Dimethylformamide → 4-(3-Chlorophenyl)-6-methyl-2-(methylthio)-1,4-dihydropyridine-5-carboxylic acid 3-phenylpropyl ester
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:24])[C:12]([C:21](=O)[CH3:22])=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN[C:27](=N)[SH:28].S([O-])([O-])(=O)=O.[C:35]([O-])(=O)[CH3:36].[Na+].C[N:41](C=O)C>>[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]([C:12]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH:36]=[C:35]([S:28][CH3:27])[NH:41][C:21]=2[CH3:22])=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Conditions
- Temperature
- 60 °C
Procedure
200 mg (0.583 mmol) of 2-acetyl-3-(3-chlorophenyl) acrylic acid 3-phenylpropyl ester was dissolved in 10 ml of DMF. 130 mg (0.467 mmol) of methylisothiourea-sulfate and 95.6 mg (1.17 mmol) of sodium acetate was added at room temperature and stirred at 60° C. for 2 days. After DMF was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 2/1) to obtain the title compound.
Workup
- customAfter DMF was evaporated under reduced pressure
- additionthe reaction mixture was diluted with ethyl acetate
- washwashed with saturated aqueous sodium chloride solution
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 2/1)
Sources & evidence
- ORD record
- ord-c6a26457c70148b49ec3ac3a56b6c7a4
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288544B2
Reaction notes
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