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Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OC1=C(C=C(C=C1)C(C)=O)SC, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:BrCCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrCCCOC1=C(C=C(C=C1)C(C)=O)SC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1-[4-hydroxy-3-(methylmercapto)phenyl]-ethanone (5.4 g; 30 mmol), K2CO3 (4.2 g), 1,3-dibromopropane (8 g, 39 mmol) in acetonitrile (150 ml) was heated at reflux for 3 hours and stirred at room temperature overnight. Acetonitrile was removed at reduced pressure and the residue was extracted into dichloromethane (250 ml). Insolubles were filtered off. The dichloromethane solution was concentrated. The crude product was purified on a silica gel column (SiO2, 100 g; eluted with 3:2 hexane:dichloromethane, 1.6 l). The compound crystallized upon concentration, and the product (3.5 g, 39%) was recrystallized from ethanol (40 ml) to yield 1-[4-(3-bromopropoxy)-3-(methylmercapto)phenyl]ethanone as white needles, 2.0 g; m.p.=120°-122° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OC1=C(C=C(C=C1)C1(CC=CC=C1)C=O)OC, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:BrCCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrCCCOC1=C(C=C(C=C1)C1(CC=CC=C1)C=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1-(4-hydroxy-3-methoxyphenyl)phenyl-methanone (14 g, 61.4 mmol), K2CO3 (13 g, 92.1 mmol), and 1,3-dibromopropane (28 g, 86 mmol) in acetonitrile (400 ml) was heated at reflux for 4 hours. The reaction was followed by thin layer chromatography. At the end of the reaction, the inorganics were filtered off and the solvent was removed on a rotary evaporator. The residue was purified on a flash chromatographic column (SiO2, 140 g, eluted with 4:1 hexane:dichloromethane, 1.2 l) to give a partially solidified material: 15.44 g (72%). Recrystallization twice from ethanol gave 2.84 g of 1-[4-(3-bromopropoxy)-3-methoxyphenyl]phenylmethanone as white crystals, m.p.=88°-89° C. |
Here is a chemical reaction formula: Reactants are m3_m4:BrCCCCl, amount is: 0.0 ;m3_m4:C(=O)N, amount is: 0.0 ;m2_m5:OC1=C(C=C(C=C1)C(C)=O)N(C)C, amount is: 0.0 ;m1_m6:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:O, amount is: 0.0 ;m2_m5:CN(C=O)C, amount is: 0.0 ;m1_m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCOC1=C(C=C(C=C1)C(C)=O)N(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of sodium hydride (2.3 g, 48.5 mmol of 50% oil dispersion) with dimethylformamide (75 ml), and cooled to 3° C. in an ice-salt bath and under a stream of nitrogen was added, dropwise, 1-(4-hydroxy-3-dimethylaminophenyl)ethanone (8.7 g, 48.5 mmol) dissolved in dimethylformamide (150 ml) so that the temperature did not go over 7° C. After the addition was over, the bath was removed and the reaction was stirred at ambient temperature for 45 minutes. The ice bath was reapplied and a solution of 1-bromo-3-chloropropane (8.4 g, 53.4 mmol) in dimethy]formamide (25 ml) was added dropwise. After the addition was complete, the reaction was stirred for 18 hours at ambient temperature under nitrogen. The reaction was chilled to 7° C. in an ice bath and water (200 ml) was carefully added. After stirring for 5 minutes, the aqueous mixture was extracted with ethyl acetate (5×200 ml). The ethyl acetate extract was washed with water (2×50 ml), dried with MgSO4, and concentrated to yield 22.2 g of a black oily liquid. The compound was purified by prep HPLC, and combination of appropriate fractions gave 5.0 g of brown oil. |
Here is a chemical reaction formula: Reactants are m1_m3:ClCCCOC1=C(C=C(C(=O)O)C=C1)OC, amount is: 0.0 ;m2:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:ClCCl, amount is: 0.0 ;m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCOC1=C(C=C(C(=O)Cl)C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4-(3-chloropropoxy)-3-methoxybenzoic acid (2.4 g, 10 mmol) in dichloromethane (5 ml) was added thionyl chloride (0.9 ml, 12 mmol) dissolved in dichloromethane (5 ml). The reaction was stirred and refluxed for 1 hour, and then the dichloromethane was removed in vacuo to leave a dark oil. The oil was triturated with hexane and the solid that formed while scratching with a glass rod was collected to afford 1.6 g of 4-(3-chloropropoxy)-3-methoxybenzoyl chloride, m.p.=60°-63° C. |
Here is a chemical reaction formula: Reactants are m1:[BH4-].[Na+], amount is: 0.0 ;m3:[BH4-].[Na+], amount is: 0.0 ;m2_m4:ClCCCOC1=C(C=C(C=C1)C(C)=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m4:C(C)O.O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCOC1=C(C=C(C=C1)C(O)C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a flask charged with sodium borohydride (1.5 g, 39.4 mmol) under nitrogen and chilled to 10° C. was added, slowly, a solution of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (6.0 g, 26.2 mmol) dissolved in ethanol-tetrahydrofuran (120 ml, 2:1). After total addition, the ice bath was removed and the reaction was stirred at ambient temperature for 3 hours. An additional amount of sodium borohydride (0.2 g, 5.3 mmol) was carefully added. After stirring at ambient temperature for one hour, the solvent was removed in vacuo. The resultant solid residue was diluted with water (100 ml) and left overnight. The product was isolated by vacuum filtration yielding 3.8 g. Two consecutive recrystallizations from toluene provided 3.3 g (55%) of 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzene methanol as a light brown solid, m.p.=107°-109° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)(=O)NC=1C=C(C=CC1O)C(C)=O, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:ClCCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)NC=1C=C(C=CC1OCCCCl)C(C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 1-[3-acetylamino-4-hydroxyphenyl]ethanone (7.7 g, 40 mmol), K2CO3 (5.7 g), 3-chloro-1-bromopropane (8.9 g, 56 mmol) and acetone (100 ml) was refluxed for 16 hours. The reaction was allowed to cool to ambient temperature and filtered. Concentration of the filtrate yielded 8.5 g of a white solid. The solid was recrystallized from toluene and then from ethanol to afford 6.5 g of an off-white solid. A 3.3 g sample of this material was flash chromatographed on silica gel with ethyl acetate as eluent. Concentration of the appropriate fractions afforded 1 2.8 g of a solid. The solid was recrystallized from toluene and then from ethanol-water to yield 2.2 g (51%) of a solid, m.p.=124°-126° C. |
Here is a chemical reaction formula: Reactants are m1_m2:CC(=O)C1=CC(OC)=C(O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)O, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE.Products are 0:C(C)C1=CC(=C(C=C1)O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Acetovanillone (Aldrich, 11.0 g, 66 mmol) was dissolved in absolute ethanol (200 ml) and added to 1.5 g of 5% palladium on carbon. A few drops of concentrated hydrochloric acid were added and the mixture hydrogenated on a shaker at 42 psi. The reaction mixture was filtered through Celite, and the filtrate was concentrated to afford 10.3 g of a golden liquid. This was diluted with water, extracted with diethyl ether and the organic phase was washed with water and sodium bicarbonate. The solvent was dried (MgSO4) and concentrated to afford 9.3 g of a slightly yellow liquid. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:C(C)(=O)NC=1C=C(C=CC1)O, amount is: 0.0 ;m1_m4_m2:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m3:BrCCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)NC=1C=C(OCCCBr)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 3-acetamidophenol (15.1 g) in dichloromethane (500 ml, dry) was added potassium carbonate (20 g) and then 1,3-dibromopropane (30 g). The resulting mixture was heated at reflux for 6 hours and then overnight at room temperature. After an additional 24 hours, the reaction was complete. Solids were filtered from the reaction mixture, and the solution was concentrated to an oil, which was purified to yield 3-(3-acetamidophenoxy)propyl bromide, 13.2 g. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[Na+], amount is: 0.0 MOLE;m1:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2)NC(C)=O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(N)C=CC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of N-[3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]acetamide (9.2 g, 22 mmol), prepared as described in the previous example, in 15% hydrochloric acid (110 ml) was heated at 100° C. for 2.5 hours until a homogeneous solution resulted. The reaction was cooled to 0° C. in an ice bath and basified with 50% NaOH. The product was extracted with ethyl acetate (3×200 ml). The ethyl acetate solution was washed with water, brine, then dried over Na2SO4. The solvent was removed. The crude product was purified on a flash chromatography column. The product thus obtained was a solid: 6.6 g (80%). Recrystallization from hot ethanol (50 ml) gave 3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-aniline as off-white crystals: 3.46 g, m.p.=115°-117° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:CN(C(C1=CC(=C(C=C1)O)OC)=O)C, amount is: 0.0 ;m1_m4_m2:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m3:BrCCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C(C1=CC(=C(C=C1)OCCCBr)OC)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To N,N-dimethyl-4-hydroxy-3-methoxybenzamide (5.64 g, 28.7 mmol) in acetonitrile (450 ml) was added potassium carbonate (7.9 g) followed by 1,3-dibromopropane (11.6 g). The resulting reaction mixture was refluxed for 3 hours and stirred at room temperature for 12 hours. The mixture was filtered and concentrated to an oil. Following purification by column chromatography, N,N-dimethyl-4-bromopropoxy-3-methoxybenzamide as a colorless oil (7.6 g) was obtained. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:CN(C(C1=CC(=C(C=C1)OCCCBr)OC)=O)C, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C(C1=CC(=C(C=C1)OCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)OC)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.9 g, 17.7 mmol), N,N-dimethyl-4-bromopropoxy-3-methoxybenzamide (5.54 g, 17.5 mmol) and K2CO3 (3 g) in acetonitrile (250 ml) was heated at reflux for one hour. At the end of the reaction, the insolubles were filtered and washed with dichloromethane. The solvent was removed on a rotary evaporator. The residue was purified by flash chromatography over a silica gel column. The product thus obtained as an oil weighed 7 g. Crystallization from hot ethanol (45 ml) afforded analytically pure N,N-dimethyl-4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide, 3.95 g, 50%, as light yellow crystals, m.p.=126°-127° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)OC)C=C1, amount is: 0.0 ;m1_m2_m3:NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=NN)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone (4.3 g, 10 mmol), prepared as in Example 3 above, hydrazine (0.8 g, 2.5 mmol), and ethanol (40 ml) was refluxed for 16 hours. The cooled solution was concentrated to yield an oily residue. The residue was triturated with water and the resultant solid was collected to afford 4.2 g of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1 -piperidinyl]propoxy]-3-methoxyphenyl]-ethanone hydrazone as a yellow solid. The compound was recrystallized from isopropanol and then from toluene to afford 1.7 g (39%), m.p.=106°-108° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC(=O)C1=CC(=C(C=C1)O)OC, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:ClC\C=C/CCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC\C=C/COC1=C(C=C(C=C1)C(C)=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 4-hydroxy-3-methoxyacetophenone (16.6 g, 10 mmole), K2CO3 (14 g, 100 mmol) and cis-1,4-dichloro-2-butene (Aldrich, 15 g, 120 mmol) in acetonitrile (250 ml) was heated at reflux for 2.5 hours. The mixture was filtered and concentrated to an oil. Purification was by flash chromatography. The fractions containing the purest product were combined and concentrated to give white crystals, 7.7 g, 30%. This was recrystallized from ether to give analytical pure (Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone (2.72 g), m.p.=64°-66° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC1=CC2=C(C(=NO2)C2CCN(CC2)C/C=C/COC=2C=C(C=CC2OCC2=CC=CC=C2)C(C)=O)C=C1, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)C/C=C/COC=2C=C(C=CC2O)C(C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The mixture of (E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-benzyloxyphenyl]ethanone (5.5 g, 10.7 mmol), acetic acid (50 ml), and hydrochloric acid (6 ml) was heated at 75° C. for 2 hours. At the end of reaction, the solvent was reduced to about 20 ml on a rotary evaporator. The solution was poured into ice water (350 ml) and extracted with dichloromethane (3×250 ml). The dichloromethane solution was washed with brine and dried over Na2SO4. A solid formed on concentration of the solvent. This was collected by filtration (3.4 g). Recrystallization from hot methanol (40 ml) gave 1.82 g of (E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-hydroxyphenyl]-ethanone hydrochloride as white crystals, 37.5%, m.p.=208°-210° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:CS(=O)(=O)OCC1COC2=C(O1)C=CC=C2, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CC2COC3=C(O2)C=CC=C3)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), K2CO3 (2.45 g, 17.7 mmol), 2-methanesulfonyloxymethyl-1,4-benzodioxan (3.35 g, 13.7 mmole) in acetonitrile (100 ml) was heated at reflux for 12 hours. At the end of the reaction, the insolubles were filtered and rinsed with dichloromethane. The organic solution was concentrated. The crude oil was purified by flash chromatography on a silica gel column. The fractions containing the pure product were pooled and concentrated to a light yellow oil (3.94 g, 74%). Crystallization from ethanol and petroleum ether gave 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]methyl-1,4-benzodioxan as off-white crystals, 2.22 g, m.p.=86°-87° C. |
Here is a chemical reaction formula: Reactants are m3:S(=O)(=O)(C)Cl, amount is: 0.0 ;m1_m4_m2:OCCC1COC2=C(O1)C=CC=C2, amount is: 0.0 ;m1_m4_m2:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:S(=O)(=O)(C)OCCC1COC2=C(O1)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To the compound 2-hydroxyethyl-1,4-benzodioxan (11.96 g) in dichloromethane (450 ml) was added triethylamine (0.12 mol, 10 ml). Mesylchloride (9.2 g) was then added dropwise and the reaction mixture was stirred for one hour at room temperature. After completion of the reaction, the solution was washed with water, brine, and concentrated to an oil, which was purified by chromatography on silica gel to yield 2-mesyloxyethyl-1,4-benzodioxan, 17.08 g. |
Here is a chemical reaction formula: Reactants are m1_m2_m5:OC=1C=C2CCCC(C2=CC1OC)=O, amount is: 0.0 ;m1_m2_m5:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m3_m4:BrCCCCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:CC(=O)C, amount is: 0.0 ;m3_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCOC=1C=C2CCCC(C2=CC1OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-hydroxy-7-methoxy-1-tetralone (J. Org. Chem., 1985, 50, 4937) (1.5 g, 7.8 mmol), K2CO3 (1.7 g, 12.3 mmol), and acetone (30 ml) was stirred at reflux under nitrogen for 45 minutes. The reaction was cooled to ambient temperature and a solution of 1-bromo-3-chloropropane (1.9 g, 12.1 mmol) dissolved in 8 ml acetone was dripped into the mixture. After total addition, the reaction was heated to reflux and stirred under nitrogen for 21 hours. The reaction was cooled to ambient temperature and filtered. The filter cake was washed well with acetone and the filtrate was concentrated to yield 2.0 g 6-(3-chloropropoxy)-7-methoxy-1-tetralone as an amber oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:BrCCCN1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (6.44 g, 29.1 mmole), K2CO3 (6.4 g, 46 mmol), N-(3-bromopropyl)phthalimide (8.4 g, 31 mmol) in acetonitrile (150 ml) was heated at reflux for 3.5 hours. The insolubles were filtered. The solvent was removed at reduced pressure and the residue was purified by silica gel column chromatography to give N-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl]phthalimide as a white solid. Recrystallization from ethanol yielded 9.8 g (83%) of off-white crystals, m.p.=129°-130° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m6:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1, amount is: 0.0 ;m1_m2_m6:O.NN, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE;m5_m7:Cl, amount is: 0.0 MOLE;m3:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m6:CO, amount is: 0.0 ;m8:CO, amount is: 0.0 MOLE;m5_m7:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.Cl.NCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-propyl]phthalimide (8.5 g, 21 mmol), hydrazine monohydrate (1.5 g, 30 mmol) in methanol (60 ml) was heated at reflux for 2 hours. At the end of the reaction, methanol was removed to leave a crude solid. To this was added water (60 ml), then the mixture was acidified with HCl to pH 1. The insolubles were filtered with the aid of a pad of Celite. The aqueous solution was basified with 50% NaOH, (pH 13), then extracted with dichloromethane. The combined dichloromethane solution was washed with brine, then dried to a colorless oil (4.5 g). The analytical sample (1.5 g) was prepared by treating the oil with HCl in ethanol at 0° C. The 1-(3-aminopropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine dihydrochloride was obtained as white crystals, 2.03 g, m.p.=231°-234° C. |
Here is a chemical reaction formula: Reactants are m4_m7:Cl, amount is: 0.0 MOLE;m1_m2_m5:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1, amount is: 0.0 ;m1_m2_m5:O.NN, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m7:C(C)O, amount is: 0.0 MOLE;m1_m2_m5:CO, amount is: 0.0 ;m6:O, amount is: 0.0 MOLE;m8:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.Cl.NCCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidinyl]-butyl]phthalimide (6.9 g, 16.4 mmol) and hydrazine monohydrate (1.64 g, 32.8 mmol) in methanol (70 ml) was heated at reflux for 3 hours. At the end of the reaction, methanol was removed to leave a crude solid. This was dissolved in water and acidified with HCl to pH 2. The insolubles were filtered. The aqueous solution was basified with 50% NaOH, and then extracted with dichloromethane. The dichloromethane solution was washed with water and brine, and then dried over MgSO4. The solvent was removed to a colorless oil: 4.48 g. This oil was treated with 2.5 equivalents of HCl in ethanol. The solid was collected. Recrystallization from ethanol (65 ml) and methanol (20 ml) gave 2.0 g of 1-(4-aminobutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine dihydrochloride as white crystals, m.p.=234°-237° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m6:CC(=O)C1=CCC(=S)C(=C1)OC, amount is: 0.0 ;m1_m2_m6:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4:C1CCCCC1, amount is: 0.0 MOLE;m3_m5:BrCCCCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m6:CC(=O)C, amount is: 0.0 ;m3_m5:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCSC1=C(C=C(C=C1)C(C)=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1-(4-thio-3-methoxyphenyl)ethanone (10.0 g, 54.9 mmol), potassium carbonate (9.0 g, 65.1 mmol), and acetone (100 ml) was stirred at reflux under nitrogen for 30 minutes. The reaction was cooled to ambient temperature and a solution of 1-bromo-3-chloropropane (6.5 ml, 9.5 g, 60.4 mmol) dissolved in acetone (25 ml) was dripped into the reaction. After complete addition, the reaction was heated to reflux and stirred under nitrogen for 17 hours. After the reaction was carried to substantial completion, the reaction mixture was filtered and the resulting filter cake was washed with acetone. The filtrate was concentrated to provide an amber oil. A small sample was solidified by trituration with hot cyclohexane to provide 1-[4-[(3-chloropropyl)thio]-3-methoxyphenyl]ethanone as a yellow solid, 11.7 g, m.p.=53°-55° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:ClCCCSC1=C(C=C(C=C1)C(C)=O)OC, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:CC#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCSC2=C(C=C(C=C2)C(C)=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), 1-[4-[(3-chloropropyl)-thio]-3-methoxyphenyl]ethanone (3.5 g, 13.6 mmol), K2CO3 (2.3 g, 16.6 mmol), KI (200 mg) and CH3CN (100 ml) was stirred at reflux under nitrogen for 7.5 hours and then was left at ambient temperature for 65 hours. The reaction was poured into water and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed twice with water, once with brine and dried over MgSO4. The solvent was removed in vacuo to afford 6.8 g of a light brown oil. The sample was purified by flash chromatography. Concentration of appropriate fractions yielded 3.0 g. Recrystallization from ethanol provided 2.4 g (41%) of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl]thio]-3-methoxyphenyl]-ethanone as a beige solid, m.p.=93°-95° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m5:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:BrCCCCC1=C(C=CC=C1)OC, amount is: 0.0 ;m1_m2_m3_m5:C(C)#N, amount is: 0.0 ;m4_m6:C(\C=C/C(=O)O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m6:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(\C=C/C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)CCCC(C2=C(C=CC=C2)OC)N2CCCCC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.36 g, 10.7 mmole), K2CO3 (2 g, 14.5 mmol) and 2-(4-bromobutyl) anisole (2.4 g, 10 mmol) in acetonitrile (100 ml) was heated at reflux for 2.5 hours. At the end of reaction, the solvent was removed. The residue was extracted into dichloromethane (200 ml) and filtered. The dichloromethane solution was concentrated. The crude oil obtained was purified on a flash chromatography column. The material thus purified was a light yellow oil (2.73 g, 53%). This oil was dissolved in ethanol and treated with maleic acid (607 mg, 1.0 eq) in ethanol. The 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-(2'-methoxyphenyl)-butylpiperidine maleate crystals formed on concentration and subsequent cooling to 0° C. These were collected and dried to yield 2.05 g, m.p.=132°-133° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:BrC1=CC=C(C=C1)C(C)=O, amount is: 0.0 ;m1_m4_m2_m3:C(CCS)S, amount is: 0.0 ;m1_m4_m2_m3:B(F)(F)F.CCOCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:ClC(Cl)Cl, amount is: 0.0 ;m5:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=CC=C(C=C1)C(C)C1SCCCS1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To the compound p-bromoacetophenone (36.85 g, 185 mmol) in trichloromethane (300 ml) was added 1,3-propanedithiol (25 g, 230 mmol) and boron trifluoride etherate (3 ml). The resulting mixture was stirred at room temperature for 48 hours. The mixture was diluted with dichloromethane (500 ml), washed twice with 10% sodium hydroxide (200 ml), water, and brine, and then dried (Na2SO4). The product was concentrated to an oil. A portion was stirred with ether (100 ml) and a crystalline product was formed. The crystalline product was recovered by filtration and purified by recrystallization to yield 4-bromo-1-(1,3-dithian-2-yl)ethylbenzene. |
Here is a chemical reaction formula: Reactants are m1_m4_m5_m2_m3:FC1=C(C=CC(=C1)F)C(=O)C1CN(CC1)CC1=CC=CC=C1, amount is: 0.0 ;m1_m4_m5_m2_m3:NO.Cl, amount is: 0.0 ;m1_m4_m5_m2_m3:C(C)(=O)[O-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5_m2_m3:C(C)O, amount is: 0.0 ;m1_m4_m5_m2_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To the compound (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone (22 g) in 95% ethanol (350 ml) and water (100 ml) was added NH2OH.HCl (10.1 g) and ammonium acetate (12.7 g, 2.1 eq). The resulting mixture was refluxed for 3.5 hours. The mixture was then allowed to stir at room temperature for 24 hours. The reaction mixture was concentrated to remove ethanol, poured into water (500 ml), and extracted with dichloromethane (500 ml). This was followed by washing with water, brine, and drying over magnesium sulfate. The product was concentrated to an oil and purified by column chromatography to yield 12 g of (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m7:FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m7:[OH-].[K+], amount is: 0.0 ;m1_m2_m3_m7:O, amount is: 0.0 ;m4_m6:C(\C=C\C(=O)O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m7:C(C)O, amount is: 0.0 ;m5:C(C)O, amount is: 0.0 MOLE;m4_m6:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CN(CC2)CC2=CC=CC=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime (10.8 g, 34.2 mmol), potassium hydroxide (10 g), water (100 ml), and ethanol (100 ml) was heated at reflux for 2 hours. At the end of the reaction, the solution was cooled and ethanol was removed on a rotary evaporator. The aqueous mixture was diluted with water (100 ml) then extracted with dichloromethane (500 ml). The organic solution was washed with brine and dried over anhydrous MgSO4. The solution was concentrated to an oil (9.8 g). The crude product was purified by flash chromatography over a silica gel column. The product thus obtained weighed 4.46 g (44%) as a light yellow oil. The oily product was dissolved in ethanol, and then treated with a solution of fumaric acid (1.73 g, 1.0 eq) in ethanol. Crystallization took place slowly with the addition of isopropyl ether. Recrystallization from ethanol (15 ml) gave 4.6 g of 6-fluoro-3-[1-(phenylmethyl)-3-pyrrolidinyl]-1,2-benzisoxazole fumarate as white crystals, m.p.=142°-144° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1, amount is: 0.0 ;m1_m3_m2_m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2_m4:ClCCl.C(C)O, amount is: 0.0 ;m1_m3_m2_m4:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 8.0 g of N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]phthalimide in dichloromethane/ethanol (150 ml) was added 1M -HCl in ether. The salt crystallized out rapidly. It was filtered off, washed with ethanol and dried to afford 8.15 g with m.p.=257°-259° C., dec. Recrystallization provided 7.20 g of pure white salt, with m.p. unchanged. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5_m6_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m5_m6_m4:Cl.ClCCCN1CCCCC1, amount is: 0.0 ;m1_m2_m3_m5_m6_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5_m6_m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5_m6_m4:C(C)#N, amount is: 0.0 ,Catalysts are m1_m2_m3_m5_m6_m4:S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2CCCCC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.0 g, 13.6 mmol), N-(3-chloropropyl)piperidine hydrochloride (4.05 g, 20.4 mmol), K2CO3 (6 g, 43.4 mmol), tetrabutylammonium hydrogen sulfate (phase transfer catalyst, 2.3 g) in acetonitrile (100 ml) and water (15 ml) was heated at reflux for 16 hours. The mixture was washed with brine and the layers were separated. The organic solution was concentrated. The crude product (6.4 g) was purified by flash chromatography over a silica gel column (55 g, sorbsil C-30; eluted with 2% CH3OH:0.5% DEA in DCM, 1.4 l). The oil thus purified (4.5 g) was treated with fumaric acid (1.6 g) in ethanol. The solid was collected: weight 3.1 g, m.p.178°-181° C. Recrystallization from ethanol yielded 2.28 g of white crystals, m.p.=190°-192° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:ClCCCOC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m1_m2_m3_m4:CC#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C3C=CNC3=CC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.6 g, 11.8 mmol), K2CO3 (1.6 g, 11.6 mmol), KI (200 mg), 5-(3-chloropropoxy)indole (2.2 g, 10.5 mmol) and CH3CN (100 ml) was stirred at reflux under N2 for 18 hours. The cooled reaction was poured into H2O and the aqueous mixture was extracted with EtOAc. The EtOAc extract was washed 2 times with H2O, 2 times with brine and after drying with MgSO4 the solvent was removed in vacuo to yield 5.1 g of a dark oil. The oil was purified by preparative HPLC (Water's Associates Prep LC/System 500, using 2 silica gel columns and 4% MeOH--CH2Cl2 as eluent) to afford 2.65 g (65%) of a beige solid. Recrystallization from ethanol gave 2.2 g (54%) of a beige powder, m.p.=118°-121° C. |
Here is a chemical reaction formula: Reactants are m5:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:ClCCCOC1=C2C=CNC2=CC=C1, amount is: 0.0 MOLE;m1_m2_m3_m4:CC#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C3C=CNC3=CC=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.5 g, 16 mmol), K2CO3 (2.2 g, 16 mmol), KI (200 mg), 4-(3-chloropropoxy)indole (3.0 g, 14 mmol CH3CN (100 ml) was stirred at reflux under N2 for 7 hours and then at ambient temperature for 68 hours. Reflux was resumed for an additional 6 hours whereupon a TLC revealed incomplete reaction. K2CO3 (0.5 g, 4 mmol) was added and the reaction was stirred at reflux for 17 hours. The cooled reaction was poured into H2O and the aqueous mixture was extracted with EtOAc. The organic extract was washed with H2O and saturated NaCl and after drying over MgSO4 the solvent was removed to afford 5.7 g of a beige solid. The product was purified by preparative HPLC (Water's Associates Prep LC/System 500 using 2 silica gel columns and 4% MeOH--CH2C2 as eluent) to yield 3.4 g (61%) of a beige solid. Two consecutive recrystallizations from EtOH provided 2.3 g (41%) of a white powder, m.p.=129°-131° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NS2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:ClCCCOC1=C(C=C(C=C1)C(C)=O)O, amount is: 0.0 ;m1_m2_m3_m4:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m1_m2_m3_m4:CC#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NS2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (2.4 g, 10.1 mmol), 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (2.5 g, 11.1 mmol), NaHCO3, (0.94 g, 11.1 mmol), KI (100 mg) and CH3CN (100 ml) was stirred at reflux under N2 for 65 hours. The cooled reaction was poured into H2O and the aqueous mixture was extracted with EtOAc. The EtOAc extract was washed with H2O (1×) and brine (3×) and after drying with MgSO4 the solvent was evaporated to give 4.2 g of a dark solid. Three consecutive recrystallizations from EtOH provided 2.1 g (48%) of glittery beige crystals m.p.=135°-137° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5_m6:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4_m5_m6:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4_m5_m6:BrCC(CO)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5_m6:O, amount is: 0.0 ;m1_m2_m3_m4_m5_m6:C(C)#N, amount is: 0.0 ,Catalysts are m1_m2_m3_m4_m5_m6:S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CO)(C)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.0 g, 13.6 mmol), K2CO3 (12.5 g, 17.5 mmol), 3-bromo-2,2-dimethyl-1-propanol (3 g, 21 mmol, 1.5 eq.), tetra-butylammonium hydrogen sulfate (1 g, phase transfer catalyst) in water (5 ml) and acetonitrile (150 ml) was heated at reflux for 43 days. TLC showed a small spot for the expected product. The mixture was diluted with EtOAc (400 ml) and washed with brine. The organic solution was dried and concentrated to a dark brown mixture. The crude mixture was purified carefully by flash chromatography (SiO2, 95 g to afford the dried pure product; 260 mg, (6%) as an oil. This oil was converted to the fumarate salt by treatment with fumaric acid (98.5 mg, 1.0 eq.) in ethanol. Recrystallization from ethanol:ether yielded 210 mg of white crystals, m.p.=144°-145° C. |
Here is a chemical reaction formula: Reactants are m2:[BH4-].[Na+], amount is: 0.0 ;m1_m3_m4:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:CO, amount is: 0.0 ;m1_m3_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]phthalimide (7.8 g, 19.8 mmol) in methanol (250 ml) and DCM (30 ml) was added NaBH4 (1.7 g, 45.5 mmol) at room temperature under nitrogen. After stirring for 0.5 hours the homogeneous reaction mixture was concentrated. The remaining solid was purified on a flash chromatography column (SiO2, 1:1 EtOAc/DCM, increased to 10% MeOH) to give 7.0 g (90%) of the desired product as a solid which was recrystallized from EtOAc, m.p.=172°-173° C. |
Here is a chemical reaction formula: Reactants are m3:CCOCC, amount is: 0.0 ;m1:FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 MOLE;m2:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 5.0 g sample of N-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]-ethyl]phthalimide was suspended in methanol (130 ml) and was made acidic with ethereal-HCl. After stirring for 1 hour, anhydrous ether (100 ml) was added and the suspension was stirred for an additional 30 minutes. The solid was collected and dried to afford 4.5 g of an off-white powder. This was combined with an additional sample (7.3 g total) and recrystallization from MeOH gave 4.3 g of the salt as an off-white powder, mp=265°-268° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(=O)OCC)C=C1, amount is: 0.0 ;m1_m3_m2:C(C)[Mg]Br, amount is: 0.0 ;m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(CC)(CC)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of ethyl 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionate (3.9 g, 12.0 mmol) in THF (100 ml) was added ethylmagnesium bromide (12.0 ml, 36.0 mmol, 3.0M in ether) at room temperature under nitrogen (mild exotherm). The reaction mixture was stirred for 17 hours at which time it was carefully quenched with NH4Cl (sat., 20 ml). The precipitated salts were dissolved into water (25 ml) and the layers were separated. The aqueous phase was extracted with EtOAc (2×) and the combined organics were washed with brine and dried (Na2SO4). Filtration and concentration gave the crude product which was purified via flash column chromatography (silica gel, 1% MeOH/DCM) to give 2.4 g (61%) of the desired product as an oil which solidified on standing, m.p.=50°-53° C. |
Here is a chemical reaction formula: Reactants are m3:C(CCCCCCCCC)(=O)Cl, amount is: 0.0 MOLE;m1_m4_m2:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1, amount is: 0.0 ;m1_m4_m2:CCN(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2=O)OC(CCCCCCCCC)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl-2,3-dihydro-3-hydroxy-1H-isoindol-1-one (1.4 g, 3.5 mmol) in DCM (30 ml) was added Et3N (1.2 ml, 8.8 mmol) followed by decanoyl chloride at 0° C. under nitrogen. After stirring for 1 h in the cooling bath, the solvent was removed using a stream of nitrogen. The remaining residue was diluted with EtOAc and the precipitated triethylamine hydrochloride was filtered off. The filtrate was concentrated and the remaining oil was flushed through alumina with ether to give 1.6 g (83%) of the desired product as a yellow oil. |
Here is a chemical reaction formula: Reactants are m3:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m1_m4_m2:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(CC)(CC)O)C=C1, amount is: 0.0 ;m1_m4_m2:C(CCCCCCCCC)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(C)C(CCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)(CC)OC(CCCCCCCCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 6-fluoro-3-[1-(3-hydroxy-3-ethylpentyl)-4-piperidinyl]-1,2-benzisoxazole (2.5 g, 7.48 mmol) in DCM (100 ml) was added decanoyl chloride (1.5 ml, 7.48 mmol) at 0° C., under nitrogen. The reaction mixture was stirred for 4 days at which time it was poured into NaHCO3 (sat., 50 ml). The layers were separated and the aqueous phase was extracted with DCM (2×). The combined organics were dried, filtered and concentrated to give the crude product which was purified via flash column chromatography (silica gel, 20-40% EtOAc/DCM). The product containing fractions were concentrated to give 3.0 g (81%) of the desired product as a yellow oil. The hydrochloride salt was prepared in anhydrous ether (60 ml) and isopropanol (1 ml) with ethereal HCl. The white salt was filtered and washed with anhydrous ether, m.p.=159°-161° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:C(Br)C1CO1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(\C=C\C(=O)O)(=O)O.O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (7.5 g, 54 mmol) and epibromohydrin (9 g, 54 mmol) in acetonitrile (150 ml) was heated at reflux for 16 hours. The mixture was filtered and concentrated to dryness. The crude product was purified by flash chromatography (SiO2, 180 g, eluted with methylene chloride (DCM), and 1-2% CH3OH in DCM). The material thus purified as off-white solids weighed 8.7 g (63%). This material (3 g) was converted to fumarate salt in ethanol and isopropyl ether to give 3.27 g of white crystals, m.p.=145°-147° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:O1C(COC2=C(C=C(C=C2)C=O)OC)C1, amount is: 0.0 ;m1_m2_m3:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(COC2=C(C=C(C=C2)C=O)OC)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 4-(2,3-epoxypropoxy)-3-methoxyphenyl methanone (4.5 g, 22.5 mmol) and 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (5.36 g, 24.3 mmol) in isopropyl alcohol (150 ml) was heated at 55° C. for 16 hours. The mixture was cooled and the solvent was removed on a rotary evaporator. The residue was purified by flash chromatography over a silica gel column (SiO2, 80 g; eluted with dichloromethane, DCM, and 1% CH3OH in DCM). The oil thus obtained solidified quickly, weight: 9.47 g. Recrystallization from ethanol and isopropyl ether, then toluene provided 8.6 g (86%) of white crystals, m.p.=107°-108° C. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC(=O)OCCCCCCCCCC, amount is: 0.0 ;m1_m2:FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.C(CCCCCCCCC)ON1N=C(C2=CC=C(C=C12)F)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of decanyl chloroformate (2.4 g, 11 mmol), and N-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimide (3.9 g, 10 mmol) was warmed on the steam bath for 15 minutes. The reaction was allowed to cool to ambient temperature, and then ether was added to the residue. The resulting solid was filtered to afford N-[2-[4-(1-decanoxy-6-fluoro-1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimide hydrochloride. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:COC1=C(C=C(C=C1)OC)O, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:ClCCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCOC1=C(C=CC(=C1)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2,5-dimethoxyphenol (29 g, 0.19 mol), K2CO3 (35 g), 3-chlorobromopropane (38.5 g, 0.25 mol) and acetone (250 ml) was stirred and refluxed for 6 hours, and then stirred at ambient temperature for 16 hours. The reaction was filtered, and the filtrate was concentrated to an orange liquid. The liquid was taken up into Et2O, and the organic layer washed with 1N NaOH, H2O, dried (MgSO4) and was concentrated to yield 37.8 g of an orange solid. An 11.7 g sample of this solid was flash chromatographed on silica gel (180 g) with 5% EtOAc/CH2Cl2 as eluent. Concentration of similar fractions gave 7.2 g of white, waxy solid, which was recrystallized from petroleum ether to afford a white solid, m.p. 48°-50° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC(=O)C1=CC(=C(C=C1O)O)OC, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:ClCCCBr, amount is: 0.0 ;m1_m2_m3_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClCCCOC1=CC(=C(C=C1OC)C(C)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2,4-dihydroxy-5-methoxyacetophenone (1.4 g, 7.7 mmol), K2CO3 (1.4 g, 10.0 mmol), 3-chlorobromopropane (1.6 g, 10.0 mmol) and acetone (25 mL) was stirred and refluxed under N2 for 16 hours. The reaction was poured into H2O, and the aqueous suspension was extracted with ethyl acetate. The extract was washed (H2O, brine) dried (MgSO4) and concentrated to yield 1.4 g of an off-white solid. Recrystallization twice from ethanol afforded 0.4 g of the alkylated phenol as a solid, m.p. 99°-101° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:ClCCCOC1=CC(=C(C=C1OC)C(C)=O)O, amount is: 0.0 ;m1_m2_m3_m4:C(=O)(O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=CC(=C(C=C2OC)C(C)=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (4.2 g, 19 mmol), 1-[4-(3-chloropropoxy)-2-hydroxy-5-methoxyphenyl]ethanone (5.0 g, 19 mmol), NaHCO3 (1.8 g, 20 mmol) and acetonitrile (120 mL) was stirred and refluxed for 16 hours. The reaction was filtered and the filtrate was concentrated to a dark oil. The oil was taken up in anhydrous ether and ethereal HCl was added to precipitate 8.7 g of an off-white hydrochloride salt. A 2.0 g sample of the salt was converted to its free base and chromatographed by preparative HPLC (silica gel with 5% MeOH/CH2 Cl2 as eluent). Concentration of the desired fractions gave 1.1 g of a white solid, which was recrystallized from EtOH to yield 0.85 g of the product, m.p. 122°-124° C. |
Here is a chemical reaction formula: Reactants are m1_m2:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CC)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (5.5 g 25 mmol) and 1,2-expoxybutane (1.89 g, 26.3 mmol) in isopropyl alcohol (100 ml) was heated at 65° C. for 2 days. This mixture was cooled and the solvent was removed to leave a brown oil which was purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, 1 l and MeOH:DCM 2%: 98%) to give an off-white solid weighing 6.3 g. Recrystallization from hot ethanol yielded 1.96 g of fine crystals, m.p. 87°-88° C. |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m3_m4_m6:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:FC1=CC2=C(C(=NO2)C2CCN(CC2)C(CO)CC)C=C1, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:C1(C=2C(C(N1)=O)=CC=CC2)=O, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:CCOCC, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:C1CCOC1, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)C(CN2C(C=3C(C2=O)=CC=CC3)=O)CC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of diethyl azodicarboxylate (DEAD, 4.9 g, 28.3 mmol) in THF (50 ml) was added dropwise to a solution of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butanol (6.9 g, 23.6 mmol), phthalimide (4.16 g, 1.2 eq), and triphenylphosphine (7.4 g, 28.3 mmol) in THF (200 ml) at room temperature. The solution was stirred at room temperature for 24 hours. After the reaction, the solvent was stripped to dryness. The residue was stirred in ether (200 ml) and the insolubles were removed by filtration. The oily residue from concentration of the ether solution was purified by two flash chromatography (SiO2, 75 g, eluted with dichloromethane, DCM, and 1-2% CH3OH in DCM) and (100 g of SiO2 ; eluted with DCM, 11, and 1% CH3OH in DCM, 1.2 l). Two close compounds were separated and the top compound on TLC (1.6 g) was recrystallized from isopropyl ether to yield 0.76 g of white crystals, m.p. 86°-88° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)(=O)N1N=C(C2=CC=C(C=C12)F)C1CCN(CC1)C, amount is: 0.0 ;m1_m3_m2:ClC(=O)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)(=O)N1N=C(C2=CC=C(C=C12)F)C1CCN(CC1)C(=O)OC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-benzoyl-6-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole (2.0 g, 5.93 mmol) in dichloromethane (100 ml) was added phenyl chloroformate (3.9 ml, 29.65 mmol) at room temperature. The reaction mixture was stirred at room temperature for 24 hours, refluxed for an additional 0.5 hours and subsequently concentrated. The remaining residue was dissolved into dichloromethane and washed with 10% HCl (aq.). The organic phase was dried (MgSO4), filtered, and concentrated to give an oil which was purified via flash column chromatography (silica gel, 20% DCM/EtOAc). Concentration of the product-containing fractions gave an oil which solidified on standing. The white solid was washed with EtOAc, leaving 0.47 g of the desired product, m.p. 137°-139° C. |
Here is a chemical reaction formula: Reactants are m3:ClCC#N, amount is: 0.0 ;m1_m2_m5:FC1=CC=C2C(=NNC2=C1)C1CCNCC1, amount is: 0.0 ;m1_m2_m5:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m4:C(Cl)Cl.CCOC(=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred suspension of 4-(6-fluoro-1H-indazol-3-yl)piperidine (4.95 g, 22.6 mmol) and NaHCO3 (2.1 g, 24.9 mmol) in dry acetonitrile (110 ml) was added chloroacetonitrile (1.6 ml, 24.9 mmol) at room temperature, under nitrogen. The suspension was warmed to reflux for 22.5 hours, cooled to room temperature, and subsequently filtered. The remaining solids were washed with DCM and the combined filtrates were concentrated. The resulting brown oil was dissolved into EtOAc and washed with water. The organic phase was dried (MgSO4), filtered and concentrated to give a brown solid which was redissolved into DCM/EtOAc and flushed through alumina with DCM. The eluent was concentrated to give 5.2 g of the desired product as a solid, m.p. 149°-151° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CC#N, amount is: 0.0 ;m1_m3_m2:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 28.399999618530273 MILLIMOLE,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of [4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]-acetonitrile (6.1 g, 23.6 mmol) in dry THF (235 ml) was added (dropwise) lithium aluminum hydride (LAH) (28.4 mmol, 1.0M in THF) at room temperature, under nitrogen. Upon complete addition, the reaction mixture was warmed to reflux for 3 hours. After cooling to 0° C. in an ice bath, the reaction was carefully quenched with water (4.0 ml). The solids were removed via filtration and washed with THF. The combined filtrates were concentrated to give 5.6 g of the desired product. This material was suspended in DCM and filtered to give the product as an off-white solid, m.p. 125°-128° C. |
Here is a chemical reaction formula: Reactants are m3:C(Cl)Cl.CO, amount is: 0.0 MOLE;m1_m4_m2:FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN, amount is: 0.0 ;m1_m4_m2:FC=1C=C2C(C(=O)OC2=O)=CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(\C=C/C(=O)O)(=O)O.FC=1C=C2C(C(=O)N(C2=O)CCN2CCC(CC2)C2=NNC3=CC(=CC=C23)F)=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-[4-(6-fluoro-1H-3-indazolyl)-1-piperidinyl]ethylamine (6.1 g, 23.3 mmol) in DMF (230 ml) was added 4-fluorophthalic anhydride (4.2 g, 25.5 mmol) at room temperature under nitrogen. The reaction mixture was warmed to 80° C. for 2.5 hours at which time it was allowed to cool to room temperature. The DMF was removed under reduced pressure to give a brown oil which was dissolved into DCM/MeOH. Purification via flash column chromatography (silica gel, 2% MeOH/DCM) afforded 3.6 g of the desired product as a white solid. The maleate salt was prepared in methanol (75 ml) using maleic acid (2.1 eq.). The precipitated salt was collected via filtration and recrystallized from acetonitrile to give a white solid, m.p. 193°-195° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C, amount is: 0.0 ;m1_m3_m2:ClC(=O)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C(=O)OC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-benzenesulfonyl-3-(1-methyl-4-piperazinyl)-1H-indazole (2.1 g, 5.89 mmol) in dichloromethane (100 ml) was added phenyl chloroformate (3.8 ml, 29.45 mmol) at room temperature. The reaction mixture was warmed to reflux for 2 hours, cooled to room temperature, and concentrated. The residue was diluted with ethyl acetate, filtered and purified via flash column chromatography (silica gel, ethyl acetate). Concentration of the product containing fractions gave an oil which solidified on standing. The product was washed well with heptane to give 1.5 g of a white solid, m.p. 112°-114° C. |
Here is a chemical reaction formula: Reactants are m1_m4:C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C(=O)OC1=CC=CC=C1, amount is: 0.0 ;m3:Cl, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCNCC1)C1=NNC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 1-benzenesulfonyl-3-(1-phenoxycarbonyl-4-piperazinyl)-1H-indazole (31.3 g, 67.7 mmol) in ethanol (500 ml) was added 50% KOH (aq.) (100 g of KOH in 100 g H2O ) at room temperature. The reaction mixture was warmed to reflux for 6.5 hours and cooled to room temperature. After adjusting the pH to about two using HCl (con., 120 ml), the volatiles were removed under reduced pressure. The remaining residue was diluted with water and removed via filtration. The aqueous filtrate was washed with EtOAc and basified to pH=8 using 50% NaOH (aq.). The product was extracted into 10:1 dichloromethane/isopropylalcohol. The combined organics were dried (MgSO4), filtered, and concentrated to give 13.0 g of desired 3-piperazin-1-yl-1H-indazole as a brown solid which was used without further purification. |
Here is a chemical reaction formula: Reactants are m3:ClCC#N, amount is: 0.0 ;m1_m2_m4:N1(CCNCC1)C1=NNC2=CC=CC=C12, amount is: 0.0 ;m1_m2_m4:C(=O)(O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1N=C(C2=CC=CC=C12)N1CCN(CC1)CC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred suspension of 3-piperazin-1-yl-1H-indazole (6.0 g, 29.7 mmol) and NaHCO3 (2.7 g, 32.7 mmol) in dry acetonitrile (125 ml) was added chloroacetonitrile (2.1 ml, 31.2 mmol) at room temperature, under nitrogen. The suspension was warmed to reflux for 17.5 hours, cooled to room temperature, and subsequently filtered. The remaining solids were washed with dichloromethane and the combined filtrates were concentrated. The resulting brown oil was purified via flash column chromatography (silica gel, 0-50% EtOAc/DCM) to give 4.0 g of product as an off-white solid, m.p. 121°-123° C. |
Here is a chemical reaction formula: Reactants are m1_m2:FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C2=CC=CC=C2C1=O)=O, amount is: 0.0 ;m1_m2:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.C(C1=CC=CC=C1)(=O)N1N=C(C2=CC=C(C=C12)F)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]ethyl]-1H-isoindol-1,3-(2H)-dione (6.0 g, 15 mmol) and benzoyl chloride (25 ml) was stirred at 175° C. under N2 for 2.0 hours. The reaction was cooled and diluted with anhydrous Et2O and the resultant hydrochloride salt was collected to yield 7.2 g. The compound was stirred in boiling absolute ethanol (300 ml) for 1 hour and then at ambient temperature overnight. The solid was collected and dried to afford 6.9 g. Recrystallization from MeOH gave 3.9 g of a light grey solid, m.p. 257°-260° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m5:NC1CN(CCC1C1=NOC2=C1C=CC(=C2)F)CC(C)O, amount is: 0.0 ;m1_m2_m5:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m5:C(C)#N, amount is: 0.0 ;m4_m7:Cl, amount is: 0.0 MOLE;m3:BrCC=1C(=CC=CC1)CBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(C)O, amount is: 0.0 MOLE;m4_m7:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CC3=CC=CC=C3C2)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred mixture of 1-(3-amino-2-hydroxypropyl-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.24 g, 7.6 mmol), K2CO3 (1.61 g, 11.7 mmol) in acetonitrile (100 ml) was added α,α'dibromo-o-xylene (1.54 g, 6.1 mmol). The mixture was heated at reflux for 4 hours then cooled. The insolubles were filtered. The dark red solution was concentrated down. The residue was purified by flash chromatography over s silica gel column (SiO2, 30 g; eluted with 1% CH3OH in dichloromethane). The product so obtained weighed 940 mg as an oil. This oil was dissolved in ethanol and was treated with a solution of HCl in ethanol (188 mg of AcCl in ethanol). The dark solids were collected and recrystallized again in ethanol to yield off-white crystals (1.01 g), m.p. 240°-243° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:BrCC(=O)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (6.77 g, 30.7 mmol), K2CO3 (5 g, 36.2 mmol) and 2-bromoacetamide (4.46 g, 32.3 mmol) in acetonitrile (250 ml) was heated to reflux for 4 hours. The insolubles were filtered and rinsed with dichloromethane (DCM). The solvents were removed. The residual solid was dissolved in DCM and upon concentration of this solution, 2.3 g of product crystallized out and was collected when the volume was reduced to about 50 ml. The rest of the product in DCM was purified by flash chromatography over a silica gel column (80 gm, SiO2 ; eluted with DCM and 1% CH3OH in DCM). The total product (4.2 g) thus purified was recrystallized from ethanol to yield 2.82 g of white crystals, m.p. 170°-172° C. dec. |
Here is a chemical reaction formula: Reactants are m3:C(Cl)Cl.CO, amount is: 0.0 MOLE;m2:FC=1C=C2C(C(=O)OC2=O)=CC1, amount is: 0.0 ;m1:FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C(C(=O)N(C2=O)CCN2CCC(CC2)C2=NNC3=CC(=CC=C23)F)=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution consisting of 2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]ethylamine (6.1 g, 23.2 mmol) in DMF (230 ml) was added 4-fluorophthalic anhydride (4.2 g, 25.5 mmol) at room temperature, under nitrogen. The reaction mixture was warmed to 80° C. for 2.5 hours at which time it was allowed to cool to room temperature. The DMF was removed under reduced pressure (<0.5 mmHg, 55° C.) to give a brown oil which was dissolved into DCM/MeOH. Purification via flash column chromatography (silica gel, 2% MeOH/DCM) afforded 3.6 g of 4-fluoro-N-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]ethyl]phthalimide. To a solution of the latter compound (3.6 g 8.8 mmol) in anhydrous THF (100 ml) was added LAH (18.4 ml of a 1.0M solution in THF, 18.4 mmol) at room temperature, under nitrogen. The reaction mixture was warmed to reflux for 4 hours. Upon cooling to room temperature, the reaction was quenched with water (1.5 ml, dropwise). The precipitated salts were removed via filtration and washed with DCM. The combined filtrates were concentrated to give a solid which was purified via flash column chromatography (silica gel, 0-8% MeOH/DCM). The product containing fractions were concentrated to give 2.4 g product as an off-white solid. The dimaleate salt was prepared in methanol using 2.4 eq. of maleic acid. The white precipitate was collected via filtration and washed with methanol, m.p. 186°-188° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:N1N=C(C2=CC=CC=C12)N1CCNCC1, amount is: 0.0 ;m1_m2_m3_m4:BrCCN1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ;m1_m2_m3_m4:C([O-])(O)=O.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1N=C(C2=CC=CC=C12)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 4-(1H-indazol-3-yl)piperazine (1.6 g, 7.9 mmol), N-(2-bromoethyl)phthalimide (2.1 g, 7.9 mmol), and sodium bicarbonate (0.7 g, 8.3 mmol) in acetonitrile (160 ml) was warmed to reflux for 24 hours. Upon cooling to room temperature, the reaction mixture was filtered through a pad of celite and the solids were washed with DCM. The combined filtrates were concentrated to give the N-[2-[4-(1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimide which was used without further purification. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3_m5:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m4_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m4_m3_m5:ClCC(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:ClCCl, amount is: 0.0 ;m1_m2_m4_m3_m5:C(Cl)(Cl)Cl, amount is: 0.0 ;m1_m2_m4_m3_m5:C(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCC(=O)N1CCC(CC1)C1=NOC2=C1C=CC(=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (4.4 g, 20 mmol), triethylamine (2.1 g, 21 mmol) in chloroform (50 ml) was added to a solution of chloroacetyl chloride (2.5 g, 22 mmol) in chloroform (100 ml) dropwise at room temperature. The mixture was stirred for 2 hours. The solution was diluted with dichloromethane (DCM, 100 ml) and then washed with H2O and brine. The solvent was removed and the oily product was purified by flash chromatography (SiO2, 50 g; eluted with DCM and 1% CH3OH in DCM). The pure product was obtained as an oil, 4.2 g. Crystallization from ethanol yielded 2.2 g of white crystals, m.p. 101°-102° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:Cl.COC=1C=C2CCNCC2=CC1OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=C2CCN(CC2=CC1OC)CC(CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 1-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.2 g, 11.6 mmol), K2CO3 (2 gm, 1.25 eq) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.3 g, 1.25 eq) in isopropyl alcohol (200 ml) was heated at reflux for 6 hours. The mixture was cooled and filtered. The solvent was removed to about 50 ml and the solution was allowed to stand overnight. Crystals (0.6 g) formed and were collected. The mother liquor was concentrated to a white solid. Recrystallization twice from ethanol yielded the product (1.95 g, m.p. 153°-154° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:FC1=CC=C2C(=NNC2=C1)C1CCNCC1, amount is: 0.0 ;m1_m4_m2_m3:BrCC(=O)N1CC2=CC=CC=C2CC1, amount is: 0.0 ;m1_m4_m2_m3:C([O-])(O)=O.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:CC#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1N(CCC2=CC=CC=C12)C(CN1CCC(CC1)C1=NNC2=CC(=CC=C12)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-(6-fluoro-1H-indazol-3-yl)piperidine (4.8 g, 18.9 mmol) in CH3CN (200 ml) was added 2-bromo-1-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethanone (4.8 g, 18.9 mmol) and sodium bicarbonate (1.9 g, 22.7 mmol) at room temperature. The reaction mixture was warmed to reflux (4 hours), cooled to room temperature and filtered through a pad of celite. The solids were washed with DCM and the combined filtrates were concentrated. The remaining residue was purified via preparative HPLC (silica gel, 5-10% MeOH/DCM) to give 4.1 g of 1-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]ethanone which was used without further purification. To a suspension of the latter (3.7 g, 9.4 mmol) in THF (100 ml) was added (dropwise) lithium aluminum hydride (11.3 ml of 1.0M solution in THF, 11.3 mmol) at room temperature, under nitrogen. The reaction mixture was warmed to reflux (5 hours), cooled to room temperature and carefully quenched with water (10 ml). The precipitated salts were removed via filtration and washed with 1:1 EtOAc/DCM. The combined filtrates were concentrated and the remaining oil was purified via flash column chromatography (silica gel, 10% MeOH/DCM) to give 2.2 g of the product. The dimaleate salt was prepared in methanol (30 ml) with maleic acid (3.0 eq.), m.p. 185°-187° C. |
Here is a chemical reaction formula: Reactants are m3_m5:C(\C=C\C(=O)O)(=O)O, amount is: 0.0 ;m1_m2:O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1, amount is: 0.0 ;m1_m2:N1CCCC2=CC=CC=C12, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m5:C(C)O, amount is: 0.0 MOLE;m4:C(C)(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CCCC3=CC=CC=C23)O)C=C1.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CCCC3=CC=CC=C23)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of N-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.41 g, 8.73 mmol), 1,2,3,4-tetrahydroquinoline (1.33 g, 10 mmol, in isopropyl alcohol (50 ml) was heated at reflux for 6 hours. The solution was cooled and the solvent was removed on a rotary evaporator. The crude solid was purified by flash chromatography over a silica gel column (SiO2, 40 g, eluted with methylene chloride DCM, and 1-3% MeOH in DCM). The product thus purified weighed 2.0 g. This material was dissolved in ethanol and was treated with a solution of fumaric acid (567 mg, 1.0 eq) in ethanol. The solids collected were recrystallized again from ethanol (50 ml) to yield 1.0 g of white crystals, as a hemifumarate, m.p. 170°-171° C. |
Here is a chemical reaction formula: Reactants are m2_m3_m5:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1, amount is: 0.0 ;m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m4:Cl.C(C1=CN=CC=C1)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m5:C(Cl)(Cl)Cl, amount is: 0.0 ;m6:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(C)OC(C)C;0:O.Cl.Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (1.17 g, 4.34 mmol) and triethylamine (1.08 g, 10.8 mmol) in chloroform (30 ml) was added nicotinoyl chloride hydrochloride (0.96 g, 5.4 mmol) in one portion. The mixture was stirred for 1 hour at room temperature. The solution was diluted with methylene chloride (DCM) and washed with brine and dried over anhydrous MgSO4. The solution was concentrated and the crude product was purified by flash chromatography over a silica gel column (SiO2, 25 g; eluted with DCM and 1-3% MeOH in DCM). The free base thus purified weighed 1.7 g. This product was treated with 1M. HCl in ethanol and recrystallized twice from methanol:isopropyl ether to yield white crystals, 1.19 g, m.p. 243°-245° C. as a dihydrochloride hydrate. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:BrCCC#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC#N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (8.5 g, 74 mmol) and 3-bromopropionitrile (8.2 g, 1.2 eq) in acetonitrile (300 ml) was heated at reflux for 24 hours. The mixture was cooled and the insolubles were filtered. The solvent was removed on a rotary evaporator and the crude product was purified by flash chromatography over a silica gel column (SiO2, 120 g). The product thus purified weighed 8.94 g. Recrystallization from ethanol yielded the nitrile as white crystals 4.3 g, m.p. 100°-101° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:FC1=CC=C2C(=NNC2=C1)N1CCNCC1, amount is: 0.0 ;m1_m2_m3:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m1_m2_m3:CC#N, amount is: 150.0 MOLE,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-fluoro-3-(4-piperazinyl)-1H-indazole (6.0 g, 2.7 mmol), NaHCO3 (2.5 g, 3.0 mmol) chloroacetonitrile (2.5 g, 3.3 mmol) and CH3CN (150 mol) was stirred at reflux under N2 for 18 hours. The cooled reaction was poured into H2O and the aqueous solution was extracted with EtOAc. The EtOAc extract was washed with H2O, washed with brine, dried with MgSO4 and concentrated to yield 7.0 g of a tan solid. A 1.3 g sample was recrystallized from EtOAc to yield 0.65 g of a beige solid, m.p. 154°-156° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:ClCCCOC1=C(C=C(C=C1)C(C)=O)OC, amount is: 0.0 ;m1_m2_m3_m4_m5:FC(C(=O)OI(OC(C(F)(F)F)=O)C1=CC=CC=C1)(F)F, amount is: 0.0 ;m1_m2_m3_m4_m5:O, amount is: 0.0 ;m1_m2_m3_m4_m5:C(F)(F)(F)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5:CC#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCOC1=C(C=C(C=C1)C(CO)=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4.3 g, 17.7 mmol), [bis(trifluoroacetoxy)iodo]benzene (15.6 g, 36.2 mmol), H2O (18 ml), CF3CO2H (2.8 ml) and CH3CN (90 ml) was refluxed for 3 hours. The CH3CN was removed under reduced pressure and the resulting yellow liquid was partitioned between H2O and CH2 Cl2. The biphasic mixture was filtered, the organic phase collected, washed with saturated NaHCO3 solution and concentrated to afford 1.5 g of an amorphous brown solid. The solid was flash chromatographed on silica gel, eluting the column with 5% EtOAc/CH2Cl2. Concentration of similar fractions afforded 0.7 g of the compound as a pale yellow solid, m.p. 99°-101° C. |
Here is a chemical reaction formula: Reactants are m1_m4:[Na+].C1(=CC=C(C=C1)S(=O)[O-])C, amount is: 0.0 ;m3:Cl, amount is: 0.0 ;m2:C(C)(C)(C)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=C(C=C1)S(=O)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of p-toluenesulfinic acid sodium salt (30 g) in H2O (100 mL) was added methyl t-butyl ether (50 mL) followed by dropwise addition of conc HCl (15 mL). After stirring 5 min, the organic phase was removed and the aqueous phase was extracted with methyl t-butyl ether. The organic phase was dried (Na2SO4) and concentrated to near dryness. Hexane was added and the resulting precipitate collected to afford p-toluenesulfinic acid; yield 22 g. |
Here is a chemical reaction formula: Reactants are m2:COC1=CC=C(CO)C=C1, amount is: 0.0 ;m3:ClC(C#N)(Cl)Cl, amount is: 0.0 ;m1_m4:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6:CCCCCC, amount is: 0.0 ;m5_m6:CO, amount is: 0.0 MOLE;m1_m4:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC(C(OCC1=CC=C(C=C1)OC)=N)(Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5 mg (0.125 mmol) of sodium hydride, at 60% in mineral oil, in suspension in 2.5 cm3 of anhydrous ether are placed, under an argon atmosphere, in a 10 cm3 round-bottomed flask equipped with a magnetic stirrer system. 156 μl (172.8 mg, 1.251 mmol) of pure 4-methoxybenzyl alcohol are then added. The resulting homogeneous solution is stirred (evolution of gas) for 30 minutes at a temperature in the region of 20° C. and it is then cooled to 0° C. 125 μl (180 mg, 1.20 mmol) of trichloroacetonitrile are then added. The reaction mixture is allowed to react for 4 hours while allowing the temperature to slowly rise to the region of 20° C. The reaction mixture is concentrated under reduced pressure until an orange-yellow oil is obtained which is redissolved in 1.7 cm3 of hexane containing 5.5 μl of dry methanol. The suspension is filtered through Celite under reduced pressure. The solids obtained are washed once with 5 cm3 of hexane and the solvents are then removed under reduced pressure. The yellow oil obtained (4-methoxybenzyl trichloroacetimidate) is dissolved in 2 cm3 of cyclohexane. 240 mg (0.81 mmol) of methyl (2R,3S)-3-t-butoxycarbonylamino-3-phenyl-2-hydroxy-propionate, 1.0 cm3 of dry dichloromethane and 4 μl of boron trifluoride etherate are then added. The reaction mixture is allowed to react at a temperature in the region of 20° C. for 13 hours. The reaction mixture is filtered through Celite and the solids are washed 3 times with 10 cm3 of a dichloromethane/cyclohexane (1/2 by volume) mixture. The resulting organic phase is washed twice with 5 cm3 of a saturated aqueous sodium hydrogencarbonate solution, 3 times with 5 cm3 of water and once with 5 cm3 of a saturated aqueous sodium chloride solution. It is dried over anhydrous magnesium sulphate. After filtration and evaporation of the solvents under reduced pressure, the residue obtained (547 mg) is purified by chromatography on a column of silica gel, the eluent being a hexane/ethyl acetate (70/30 by volume) mixture. There are obtained 282 mg of a solid which is recrystallized from the dichloromethane/hexane mixture at 0° C. After separation of the crystals obtained (impurities), the liquid phase ("mother liquors") is evaporated under reduced pressure. There are obtained, with a yield of 68%, 228 mg (0.55 mmol) of methyl (2R,3S)-3-t-butoxy-carbonylamino-3-phenyl-2-[(4-methoxybenzyl)oxy]-propionate, the characteristics of which are the following: |
Here is a chemical reaction formula: Reactants are m1_m5:C1(=CC=CC=C1)S(=O)[O-].[Na+], amount is: 0.0 ;m2_m3:C(C1=CC=CC=C1)(=O)N, amount is: 0.0 ;m2_m3:C(C1=CC=CC=C1)=O, amount is: 0.0 ;m4:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(=O)O, amount is: 0.0 ;m1_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)S(=O)(=O)C(C1=CC=CC=C1)NC(C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 40.2 g of sodium phenylsulphinate in 200 cm3 of water is introduced into a 500 cm3 reactor equipped with a magnetic stirrer and a reflux condenser. A mixture of 12.35 g of benzamide and 21.22 g of benzaldehyde is then added. 60 cm3 of methanol are then added so as to obtain an off-white emulsion and then 7.54 cm3 of formic acid (d=1.22) are added. After stirring for 41 hours 30 minutes at a temperature in the region of 20° C., the mixture is heated for 3 hours at 65° C. After filtration through sintered glass No. 4, the product obtained is washed with twice 15 cm3 of isopropyl ether and then with twice 15 cm3 of water. After drying, there are obtained, with a yield of 15.6%, 5.48 g of N-(α-phenylsulphonyl-benzyl)benzamide. |
Here is a chemical reaction formula: Reactants are m2:C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O, amount is: 0.0 MOLE;m1_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 11.7 ml (136.3 mmol) of oxalyl chloride were dissolved in 150 ml of CH2Cl2. The solution was cooled at -10° C. and 20 g (80.2 mmol) of commercially available 2-phenylquinoline-4-carboxylic acid were added portionwise. The reaction mixture was left overnight at room temperature and then evaporated to dryness to yield 22 g of the title compound, used without further purification. |
Here is a chemical reaction formula: Reactants are m2:COC1=CC=C2C(=CC(=NC2=C1)C1=CC=CC=C1)C(=O)O, amount is: 0.0 ;m1_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:ClCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC1=CC=C2C(=CC(=NC2=C1)C1=CC=CC=C1)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.8 ml (32.3 mmol) of oxalyl chloride were dissolved in 60 ml of CH2 Cl2. The solution was cooled at -10° C. and 6 g (19.0 mmol) of 7-methoxy-2-phenylquinoline-4-carboxylic acid were added portionwise. The reaction mixture was left overnight at room temperature and then evaporated to dryness to yield 7 g of the title compound, used without further purification. |
Here is a chemical reaction formula: Reactants are m1_m2:COC1=CC=C2C(=CC(=NC2=C1)C1=CC=CC=C1)C(=O)O, amount is: 0.0 ;m1_m2:I, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:I.OC1=CC=C2C(=CC(=NC2=C1)C1=CC=CC=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.5 g (5.4 mmol) of 7-methoxy-2-phenylquinoline-4-carboxylic acid were added portionwise to 50 ml of 57% aqueous HI. The reaction mixture was refluxed and vigourously stirred for 5 hours; then it was evaporated in-vacuo to dryness to yield 2.1 g of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N1C(=O)C(=O)C2=CC=CC=C12, amount is: 0.0 ;m1_m2_m3:C(C)(=O)C=1SC=CC1, amount is: 0.0 ;m1_m2_m3:[OH-].[K+], amount is: 0.0 ;m4:CCO, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:S1C(=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5 g (34.0 mmol) of isatin, 4.4 ml (40.8 mmol) of 2-acetylthiophene and 6.3 g (112.2 mmol) of potassium hydroxide were dissolved in 40 ml of abs. EtOH and the slurry heated at 80° C. for 16 hours. After cooling of the reaction mixture, 50 ml of water were added and the solution extracted with 50 ml of Et2O. The ice-cooled aqueous phase was acidified to pH 1 with 37% HCl and the precipitate collected by filtration and washed with water. The crude product obtained was dried in-vacuo at 40° C. and triturated with EtOAc to yield 4.8 g of the title compound. |
Here is a chemical reaction formula: Reactants are m4:CCO, amount is: 0.0 MOLE;m1_m2_m3:N1C(=O)C(=O)C2=CC=CC=C12, amount is: 0.0 ;m1_m2_m3:C(C)(=O)C=1OC=CC1, amount is: 0.0 ;m1_m2_m3:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O1C(=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5 g (34.0 mmol) of isatin, 4 ml (40.8 mmol) of 2-acetylfuran and 6.3 g (112.2 mmol) of potassium hydroxide were dissolved in 40.9 ml of abs. EtOH and the slurry heated at 80° C. for 12 hours. After cooling of the reaction mixture, 50 ml of water were added and the solution extracted with 50 ml of Et2O. The ice-cooled aqueous phase was acidified to pH 1 with 37% HCl and the precipitate collected by filtration and washed with water. The crude product obtained was dried in-vacuo at 40° C. to yield 8.5 g of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m2:O1C(=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:ClCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:O1C(=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5.2 ml (60.4 mmol) of oxalyl chloride were dissolved in 70 ml of CH2 Cl2. The solution was cooled at -10° C. and 8.5 g (35.5 mmol) of 2-(2-furyl)quinoline-4-carboxylic acid were added portionwise. The reaction mixture was left overnight at room temperature and then evaporated to dryness to yield 9.2 g of the title compound, used without further purification. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m2:Cl.N1=CC=C(C=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:ClCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.N1=CC=C(C=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.3 ml (10.4 mmol) of oxalyl chloride were dissolved in 60 ml of CH2 Cl2. The solution was cooled at -10° C. and 3.0 g (14.4 mmol) of 2-(4-pyridyl)quinoline-4-carboxylic acid hydrochloride were added portionwise. The reaction mixture was left 72 hours at room temperature and then evaporated to dryness to yield 4.0 g of the title compound, used without further purification. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:[N+](=[N-])=C, amount is: 0.0 MOLE;m1_m3_m2_m4:C(C)(C)(C)C1=C(C=CC=C1)OC(=O)CC(C)(C)NS(=O)(=O)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:CCOCC, amount is: 0.0 MOLE;m1_m3_m2_m4:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CN(S(=O)(=O)C(F)(F)F)C(CC(=O)OC1=C(C=CC=C1)C(C)(C)C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A freshly prepared solution of diazomethane in anhydrous ether was added in excess to a solution of N-[2-(2-tert-butylphenylcarboxy)-1,1-dimethylethyl]-trifluoromethanesulfonamide (13.1 g) in ether. The resulting yellow solution was allowed to stand at RT overnight, then was washed with 10% HCl followed by 2.5N aq NaOH. The organic solution was dried (MgSO4), and concentrated to afford 13.0 g of pure N-methyl-N-[2-(2-tert-butylphenylcarboxy)-1,1-dimethylethyl]trifluoromethanesulfonamide as a white solid, a 96% yield. m.p. 42°-44° C. |
Here is a chemical reaction formula: Reactants are m5:CI, amount is: 0.0 ;m6:C(CC(O)(C(=O)O)CC(=O)O)(=O)O, amount is: 0.0 ;m1_m2:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2:C1CCCCC1, amount is: 0.0 ;m4:CC(C)(C)[Si](C1=C(C(=O)N(CC)CC)C=CC=C1F)(C)C, amount is: 0.0 ;m8_m3:CN(C)CCN(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:C1CCOC1, amount is: 0.0 MOLE;m8_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)[Si](C1=C(C(=O)N(CC)CC)C(=CC=C1F)C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.3M s-BuLi in cyclohexane (1.8 mL, 2.3 mmol) was added dropwise with stirring to THF (20 mL) and TMEDA (0.32 g, 2.76 mmol), cooled to -78° C. under nitrogen. To this mixture was added dropwise the compound of Example 9 (0.6 g, 2 mmol), dissolved in a minimum amount of THF. After stirring for 10 min, MeI (0.98 g, 6.9 mmol) was injected. The mixture was stirred for 1 h; 15 mL of 25% citric acid was added and the mixture extracted with ether 3 times. The ether extracts were combined and washed twice with water, dried (MgSO4), and concentrated. The crude product was purified by RC, eluting with 3:7 ethyl acetate/hexanes. The title compound was obtained as a light yellow oil in a 31% yield. |
Here is a chemical reaction formula: Reactants are m1_m2:C(CC)N(C(C1=C(C=CC=C1)[Si](C)(C)C)=O)CCC, amount is: 0.0 MOLE;m1_m2:CI, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)N(CCC)CCC)C(=CC=C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound of Example 13 was reacted with MeI sing General Method A to prepare the title compound. |
Here is a chemical reaction formula: Reactants are m4:C[Si](C)(C)Cl, amount is: 0.0 ;m1_m2_m3:C(C)N(C(C1=CC(=CC=C1)Cl)=O)CC, amount is: 0.0 ;m1_m2_m3:ClC=1C=C(C(=O)O)C=CC1, amount is: 0.0 MOLE;m1_m2_m3:C(C)NCC, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C(=C(C(=O)N(CC)CC)C=CC1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N,N-diethyl-3-chlorobenzamide (10.45 g, 50 mmol) (prepared from 3-chlorobenzoic acid and diethylamine using the procedures described above) was reacted with TMSCl (16.30 g, 150 mmol) using General Method A to afford 13.4 g of the title compound as an orange oil in 95% yield. |
Here is a chemical reaction formula: Reactants are m1_m6_m2_m4:C[Si](C)(C)[N-][Si](C)(C)C.[Na+], amount is: 0.0 MOLE;m1_m6_m2_m4:ClC1=C(C(=O)NCC)C(=CC=C1)[Si](C)(C)C, amount is: 0.0 ;m1_m6_m2_m4:C1CCOC1, amount is: 0.0 ;m1_m6_m2_m4:C1CCOC1, amount is: 0.0 ;m3_m5:C(C)(=O)Cl, amount is: 0.0 ;m3_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(=O)N(C(C1=C(C=CC=C1[Si](C)(C)C)Cl)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1M sodium bis(trimethylsilyl)amide in THF (5.5 mL, 5.5 mmol) was added dropwise over several min to a solution of the compound of Example 45 (1.28 g, 5 mmol) in THF (30 mL). The resulting mixture was cooled with a water bath while a solution of acetyl chloride (0.432 g, 5.5 mmol) in THF (10 mL) was added, maintaining the internal reaction temperature -25° C. After 1 h, the resulting reaction mixture was partitioned between sat aq NaHCO3 and ether. The ether phase was dried (MgSO4), concentrated, and purified by RC with 1:4 ethyl acetate/hexanes to afford 0.25 g of the title compound as a pale yellow oil, a 17% yield. |
Here is a chemical reaction formula: Reactants are m1:C(C)NC(C1=CC=CC=C1)=O, amount is: 0.0 ;m2:C[Si](C)(C)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC=C1)[Si](C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-Ethylbenzamide (74.5 g, 500 mmol) and TMSCl (135.8 g, 1.25 mol) were combined according to General Method C and purified by HPLC with 1:4 ethyl acetate/hexanes to afford 75.59 g of the title compound, as a white solid, a 68% yield. m.p. 64.0°-66.0° C. |
Here is a chemical reaction formula: Reactants are m5_m1_m2_m4:C[Si](C)(C)[N-][Si](C)(C)C.[Na+], amount is: 0.0 ;m5_m1_m2_m4:C(C)NC(C1=C(C=CC=C1)[Si](C)(C)C)=O, amount is: 0.0 ;m3:COCCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m1_m2_m4:C1CCOC1, amount is: 0.0 ;m5_m1_m2_m4:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC=C1)[Si](C)(C)C)=O)COC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 1M THF solution of sodium bis(trimethylsilyl)amide (52.5 mL, 52.5 mmol) was added dropwise over 5 min to a solution of the compound of Example 49 (11.07 g, 50 mmol) in THF (100 mL). The resulting mixture was cooled with a dry ice/acetone bath while neat chloromethyl methyl ether (4.83 g, 60 mmol) was added, maintaining the internal reaction temperature <-70° C. The cold bath was removed and the resulting reaction mixture was allowed to warm for 1 h, then was partitioned between sat aq NaHCO3 and ether. The ether phase was dried (MgSO4), concentrated, and purified by HPLC with 3:17 ethyl acetate/hexanes to afford 6.55 g of the title compound as a colorless oil, a 49% yield. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)N(C(C1=C(C(=CC=C1C=O)F)[Si](C)(C)C)=O)CC, amount is: 0.0 ;m1_m2_m3:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C(=CC=C1CO)F)[Si](C)(C)C)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound of Example 41 (1.2 g, 4.1 mmol) and sodium borohydride (200 mg, 5.3 mmol) in ethanol (20 mL) were stirred at ambient temperature for 2 h. The solution was concentrated and partitioned between ether and 10% citric acid. The ether layer was washed with water and then brine, dried (MgSO4), concentrated, and recrystallized from cold hexanes to afford 1.0 g of the title compound, an 82% yield. m.p. 107°-108° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)NCC, amount is: 0.0 ;m1_m2:FC1=C(C(=O)Cl)C=C(C=C1)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC(=C1)F)F)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Diethyl amine (15.4 g, 210 mmol) and 2,5-difluorobenzoyl chloride (17.6 g, 100 mmol) were reacted using General Method E1 to afford 20.0 g of N,N-diethyl-2,5-difluorobenzamide as a clear oil, a 94% yield. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)N(C(C1=C(C=C(C=C1)C)[Si](C)(C)C)=O)CC, amount is: 0.0 MOLE;m1_m2:ClC(C(Cl)(Cl)Cl)(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=C(C=C1[Si](C)(C)C)C)Cl)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from the compound of Example 58 and 1.2 eq hexachloroethane according to General Method A. Purification by HPLC with 1:9 ethyl acetate/hexanes afforded 1.6 g of the title compound as a clear oil, a 54% yield. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)N(C(C1=C(C=C(C=C1)C)[Si](C)(C)C)=O)CC, amount is: 0.0 MOLE;m1_m2:CI, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=C(C=C1[Si](C)(C)C)C)C)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from the compound of Example 58 and MeI (4.0 eq) according to General Method A. Purification by HPLC with 3:17 ethyl acetate/hexanes gave 1.4 g of the title compound as a clear oil, an 83% yield. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5_m7:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m3_m4_m5_m7:C1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m5_m7:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4_m5_m7:C(C)NC(=O)C1=CSC=C1, amount is: 0.0 ;m1_m2_m3_m4_m5_m7:CN(C)CCN(C)C, amount is: 0.0 ;m6:C[Si](C)(C)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5_m7:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)NC(=O)C1=C(SC=C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.3M s-BuLi in cyclohexane (37.23 mL, 48.4 mmol) was added dropwise to a dry-ice/acetone cooled solution of N-ethyl-3-thiophenecarboxamide (3.41 g, 22 mmol) and TMEDA (5.62 g, 48.4 mmol) in THF (100 mL). After stirring for 30 min at -78° C., TMSCl (5.26 g, 48.4 mmol) was added in a single portion. The reaction was allowed to slowly warm to -10° C. over 1 h, then was quenched with dilute aq citric acid and extracted with ethyl acetate (3×). The combined organic solutions were dried (MgSO4), concentrated, and purified by HPLC with 3:7 EtOAc/hexanes to give 1.4 g of the title compound as a white solid, a 28% yield. m.p. 114°-116° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)N(C(C1=C(C(=CC=C1)F)[Si](C)(C)C)=S)CC, amount is: 0.0 MOLE;m1_m2:CI, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C(=C(C=C1)C)F)[Si](C)(C)C)=S)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from the compound of Example 74 and 3.0 eq MeI according to General Method A and recrystallized from cold hexanes/ethyl acetate to give 2.5 g of the title compound, an 82% yield. m.p. 96°-97° C. |
Here is a chemical reaction formula: Reactants are m2:C(C)N, amount is: 0.0 MOLE;m1:FC(C1=C(C(=O)Cl)C=CC=C1)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC=C1)C(F)(F)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(Trifluoromethyl)benzoyl chloride and ethyl amine were combined according to General Method E1 and recrystallized from cold hexanes to give 7.7 g N-ethyl-2-(trifluoromethyl)benzamide as a white solid, a 67% yield. m.p. 73°-76° C. |
Here is a chemical reaction formula: Reactants are m1_m2:[BH4-].[Na+], amount is: 0.0 ;m1_m2:C(C)N(C(C1=C(C=CC=C1C=O)[Si](C)(C)C)=O)CC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:CCOCC, amount is: 0.0 MOLE;m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC=C1CO)[Si](C)(C)C)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium borohydride (1.0 g, 26.4 mmol) was added to a solution of N,N-diethyl-2-trimethylsilyl-6-formylbenzamide, prepared in Example 97, (5.54 g, 20 mmol) in absolute ethanol (100 mL). After 3 h the mixture was diluted with ether, extracted three times with brine, dried (MgSO4), concentrated, and recrystallized from 1:1 ethyl acetate/hexanes to afford 4.12 g of N,N-diethyl-2-trimethylsilyl-6-hydroxymethylbenzamide as a white solid, a 74% yield. m.p. 81°-82.5° C. |
Here is a chemical reaction formula: Reactants are m1:FC1=C(C(=O)Cl)C=CC=C1, amount is: 0.0 ;m2:C(C)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC=C1)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Fluorobenzoyl chloride (2 g, 12.6 mmol) and 70% aq ethyl amine (1.78 g, 27.7 mmol) were combined in CH2Cl2 according to General Method E1, and kugelrohr distilled to give 1.85 g of N-ethyl-2-fluorobenzamide as a colorless oil, an 87% yield. |
Here is a chemical reaction formula: Reactants are m4:C[Si](C)(C)Cl, amount is: 0.0 ;m1_m2_m7_m3_m5_m6:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m7_m3_m5_m6:C1CCCCC1, amount is: 0.0 ;m1_m2_m7_m3_m5_m6:C(C)NC(C1=C(C=CC=C1)F)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m8:O, amount is: 0.0 ;m1_m2_m7_m3_m5_m6:C1CCOC1, amount is: 0.0 ;m1_m2_m7_m3_m5_m6:CCOCC, amount is: 0.0 ;m1_m2_m7_m3_m5_m6:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC=C1[Si](C)(C)C)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (20.3 mL, 26.4 mmol) was added to an ether/liquid nitrogen cooled solution of N-ethyl-2-fluorobenzamide (2.00 g, 11.98 mmol) in THF (75 mL) and ether (75 mL), maintaining the internal reaction temperature ≤-95° C. The resulting mixture was stirred at this temperature for 30 min, then TMSCl (1.43 g, 13.2 mmol) was added and the mixture warmed to -60° C. After 2 h, the reaction was poured into water (200 mL). The organic layer was dried (MgSO4), concentrated, and purified by silica gel chromatography, eluted with 3:7 ethyl acetate/hexanes, to afford 0.45 g of the title compound as a white solid, a 16% yield. m.p. 86°-87° C. |
Here is a chemical reaction formula: Reactants are m5:C[Si](C)(C)Cl, amount is: 0.0 ;m4_m7:FC=1C=C(C(=O)N2CCCC2)C=CC1, amount is: 0.0 ;m3_m6:CN(C)CCN(C)C, amount is: 0.0 ;m1_m2_m8:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m8:C1CCCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7:C1CCOC1, amount is: 0.0 MOLE;m3_m6:C1CCOC1, amount is: 0.0 ;m1_m2_m8:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC=1C(=C(C(=O)N2CCCC2)C(=CC1)[Si](C)(C)C)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (23.91 mL, 31.1 mmol) was added to an ether/liquid N2 cooled (-90° C.) solution of TMEDA (3.97 g, 34.2 mmol) in THF (40 mL), followed by the addition of a solution of N-(3-fluorobenzoyl)pyrrolidine (5.0 g, 25.9 mmol) in a minimum volume of THF. The resulting reaction mixture was stirred at -90° C. for 15 min, then TMSCl (6.75 g, 62.2 mmol) was added in a single portion. The reaction was warmed to RT, quenched with dilute aq citric acid, then was extracted with ether (3×). The combined ether extracts were dried (MgSO4), concentrated, and purified by HPLC with 3:7 EtOAc/hexanes to afford 0.45 g of the title compound as an oil, a 45% yield, which solidified on standing to a white solid. m.p. 97°-100° C. |
Here is a chemical reaction formula: Reactants are m1:C(C)N(C(C1=C(C=CC=C1)[Si](C)(C)C)=O)COC, amount is: 0.0 ;m2:CI, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC=C1[Si](C)(C)C)C)=O)COC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound of Example 50 (1.33 g, 5.0 mmol) and MeI (2.8 g, 20 mmol) were combined according to General Method B. The resulting reaction was partitioned between ethyl acetate and sat aq NaHCO3. The organic phase was washed with brine, dried (MgSO4), and concentrated to afford a quantitative yield of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are m3_m5:C(C)I, amount is: 0.0 ;m6_m1_m2_m4:C[Si](C)(C)[N-][Si](C)(C)C.[Na+], amount is: 0.0 ;m6_m1_m2_m4:C(C)OCCNC(C1=C(C=CC=C1[Si](C)(C)C)Cl)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C1CCOC1, amount is: 0.0 ;m6_m1_m2_m4:C1CCOC1, amount is: 0.0 ;m6_m1_m2_m4:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)N(CC)CCOCC)C(=CC=C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 1M THF solution of sodium bis(trimethylsilyl)amide (7.7 mL, 7.7 mmol) was added dropwise over 5 min to a solution of N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamide (2.1 g, 7 mmol) in THF (30 mL). The resulting mixture was stirred for 1 h at RT, then a solution of ethyl iodide (1.31 g, 8.4 mmol) in THF (15 mL) was added with a mild exotherm. The resulting reaction mixture was stirred overnight, then was partitioned between ethyl acetate and dilute aq citric acid. The ethyl acetate phase was washed with sat aq NaHCO3 followed with brine, then was dried (MgSO4) and concentrated to afford 1.9 g of the title compound as an amber oil, an 83% yield. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)N(C(C1=C(C=CC=C1[Si](C)(C)C)C)=O)COC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)#N, amount is: 0.0 ;m1_m2_m3:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC=C1[Si](C)(C)C)C)=O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound of Example 127 (0.80 g, 2.9 mmol) was refluxed in a mixture of acetonitrile (20 mL) and 2N HCl (20 mL). Within 2 h the reaction was complete by GLC, and was cooled and partitioned between ether and water. The ether phase was concentrated and purified by RC with 1:4 ethyl acetate/hexanes, then recrystallized from hexanes to give 160 mg of the title compound as a solid, a 21% yield. |
Here is a chemical reaction formula: Reactants are m5_m7:ClC(C(Cl)(Cl)Cl)(Cl)Cl, amount is: 0.0 ;m1_m2:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2:C1CCCCC1, amount is: 0.0 ;m3_m4_m6:C(C)NC(=O)C1=CSC=C1, amount is: 0.0 ;m3_m4_m6:CN(C)CCN(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m7:C1CCOC1, amount is: 0.0 ;m3_m4_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)NC(=O)C1=C(SC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (44 mL, 57.2 mmol) was added dropwise to a -78° C. cooled solution of N-ethyl-3-thiophenecarboxamide (4.04 g, 26 mmol) and TMEDA (6.65 g, 57.2 mmol) in THF (100 mL). After stirring for 30 min at -78° C., a solution of hexachloroethane (13.54 g, 57.2 mmol) in THF (20 mL) was added dropwise. The resulting reaction mixture was warmed to RT over 1 h, quenched with dilute aq citric acid, and extracted with EtOAc (3×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 3:7 EtOAc/hexanes to give 2.8 g of N-ethyl-2-chloro-3-thiophenecarboxamide as a yellow oil, a 57% yield. |
Here is a chemical reaction formula: Reactants are m5:C[Si](C)(C)Cl, amount is: 0.0 ;m3_m4_m6:C(C)NC(=O)C1=C(SC=C1)Cl, amount is: 0.0 ;m3_m4_m6:CN(C)CCN(C)C, amount is: 0.0 ;m1_m2_m7:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m7:C1CCCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4_m6:C1CCOC1, amount is: 0.0 ;m1_m2_m7:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1SC=C(C1C(=O)NCC)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (16.15 mL, 21 mmol) was added dropwise to an ether/liquid N2 cooled (-100° C.) solution of N-ethyl-2-chloro-3-thiophenecarboxamide (1.90 g, 10 mmol) and TMEDA (3.17 mL, 21 mmol) in THF (100 mL). After stirring for 30 min at -100° C., TMSCl (2.28 g, 21 mmol) was added in a single portion. The resulting reaction mixture was warmed to -25° C. over 1 h, quenched with dilute aq citric acid, and extracted with EtOAc (3×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 3:17 EtOAc/hexanes to afford 0.3 g of the title compound as a white solid, an 11% yield. m.p. 46°-48° C. |
Here is a chemical reaction formula: Reactants are m6:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4_m5_m8:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m3_m4_m5_m8:C1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m5_m8:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4_m5_m8:C(C)N(C(C1=CC=CC=C1)=O)C(C(C)(C)C)OC, amount is: 0.0 ;m1_m2_m3_m4_m5_m8:CN(C)CCN(C)C, amount is: 0.0 ;m7:C[Si](C)(C)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5_m8:C1CCOC1, amount is: 0.0 ;m9:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC=C1)[Si](C)(C)C)=O)C(C(C)(C)C)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (140.6 mL, 182.8 mmol) was added dropwise to a dry-ice/acetone cooled solution of N-ethyl-N-(1-methoxy-2,2-dimethylpropyl)benzamide (35 g, 140.6 mmol) and TMEDA (25.44 mL, 168.6 mmol) in THF (280 mL), maintaining the internal reaction temperature ≤-60° C. The yellow solution was stirred at -78° C. for 1 h, then was cannulated into a dry-ice/acetone cooled solution of TMSCl (26.72 mL, 210.6 mmol) in THF (140 mL) at a rate which maintained the internal reaction temperature ≤-55° C. The resulting mixture was warmed to 0° C. and partitioned between ether and sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and kugelrohr distilled under vacuum to give 44.8 g of the title compound as a pale yellow solid, a 99% yield. m.p. 76°-78° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)N(C(C1=C(C=CC=C1)NC(C)(C)C)=O)C, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:CI, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC=C1)N(C(C)(C)C)C)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-ethyl-N-methyl 2-(N-tert-butylamino)benzamide (1.89 g, 8.1 mmol), potassium carbonate (2.2 g, 15.9 mmol), and methyl iodide (2.3 g, 16.2 mmol) in DMF (40 mL) was heated overnight at 40° C., then was partitioned between EtOAc and water. The EtOAc was dried (MgSO4), concentrated, and purified by HPLC with 1:4 ethyl acetate/cyclohexane to afford 1.923 g of N-ethyl-N-methyl 2-(N-methyl-N-tert-butylamino)benzamide as a yellow oil, a 96% yield. |