Methanol → HCID 10046859, compound

HRID 2214081Notes

Reaction equation

HRID 2214081 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][CH2:8][C:7]1([F:12])[F:11].[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][CH2:8][C:7]2([F:11])[F:12])[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

5

Reactant 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 164537Methanol, magnesium salt (2:1)HCID 67482103HCID 67482103, compound

Product 1

HCID 10046859HCID 10046859, compoundYield 23%

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(3,4-dichloro-phenyl)-3-(2,2-difluoro-cyclopentyl)-propionic acid methyl ester (265 mg, 0.73 mmol) and 2-aminothiazole (18 mg, 0.18 mmol) in a solution of magnesium methoxide in methanol (7.4 wt. %, 0.28 mL, 0.19 mmol) was heated to 110° C. for 18 h. At this time, the reaction mixture was cooled to 25° C. and then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(2,2-difluoro-cyclopentyl)-N-thiazol-2-yl-propionamide (8.3 mg, 23%) as a yellow oil: EI-HRMS m/e calcd for C17H16F2Cl2N2OS (M+H)+ 405.0402, found 405.0407.

Workup

  1. temperatureAt this time, the reaction mixture was cooled to 25° C.
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c291068e04dd446d9d37729ea944307d
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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