Methanol → HCID 10250691, compound

HRID 854830Notes

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][C:8]([F:12])([F:11])[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][C:8]([F:11])([F: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

Reactant 4

HCID 887Methanol

HCID 21552-Aminothiazole

HCID 164537Methanol, magnesium salt (2:1)

HCID 67482130HCID 67482130, compound

Product 1

HCID 10250691HCID 10250691, compoundYield 49.6%

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-(3,4-dichloro-phenyl)-3-(3,3-difluoro-cyclopentyl)-propionic acid methyl ester (75 mg, 0.22 mmol) and 2-aminothiazole (27 mg, 0.26 mmol) in a solution of magnesium methoxide in methanol (7.4 wt. % , 0.63 mL, 0.44 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, 70/30 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(3,3-difluoro-cyclopentyl)-N-thiazol-2-yl-propionamide (44.2 mg, 49%) as an off-white solid: mp 154-156° C.; FAB-HRMS m/e calcd for C17H16F2Cl2N2OS (M+H)3 405.0402. found 405.0404.

Workup

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

Sources & evidence

ORD record: ord-6061e7b24895463dba07473c2dfcd570
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259166B2

Reaction notes

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