Methanol → 2-(3,4-dichloro-phenyl)-3-(3-methoxy-cyclopentyl)-N-thiazol-2-yl-propionamide
Reaction equation
CO[C:3](=[O:21])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([O:11][CH3:12])[CH2:7]1.[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C[O-].[Mg+2].C[O-].CO>>[Cl:20][C:15]1[CH:14]=[C:13]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH:8]([O:11][CH3:12])[CH2:7]2)[C:3]([NH:22][C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[O:21])[CH:18]=[CH:17][C:16]=1[Cl:19]Participants
Conditions
- Temperature
- 25 °C
Procedure
2-(3,4-Dichloro-phenyl)-3-(3-methoxy-cyclopentyl)-propionic acid methyl ester (118.3 mg, 0.36 mmol) and 2-aminothiazole (35.8 mg, 0.36 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 2.6 mL, 1.79 mmol). The resulting reaction mixture was then heated under reflux for 30 h. The reaction mixture was allowed to cool to 25° C. and then filtered through celite. The celite was thoroughly washed with ethyl acetate, and the filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 40% ethyl acetate/hexanes) afforded the 2-(3,4-dichloro-phenyl)-3-(3-methoxy-cyclopentyl)-N-thiazol-2-yl-propionamide (9.6 mg, 7%) as a white glass: (ES)+-HRMS m/e calcd for C18H20Cl2N2O2S (M+H)+ 399.0696, found 399.0700.
Workup
- customThe resulting reaction mixture
- temperaturewas then heated
- temperatureunder reflux for 30 h
- filtrationfiltered through celite
- washThe celite was thoroughly washed with ethyl acetate
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-85b754f961d44220950c26dd518df801
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105671B2
Reaction notes
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