2-Aminothiazole → 2-(4-benzyloxy-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

HRID 1935221Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:19][CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:31][C:32]1[S:33][CH:34]=[CH:35][N:36]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C)C=O.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[C:16]([NH:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(4-benzyloxy-phenyl)-3-cyclopentyl-propionic acid (0.15 g, 0.46 mmol) in methylene chloride (4.6 mL) was cooled to 0° C. and then treated with a 2.0M solution of oxalyl chloride in methylene chloride (0.25 mL, 0.50 mmol) and a few drops of N,N-dimethylformamide. The reaction mixture was stirred at 0° C. for 10 min and at 25° C. for 30 min. The reaction mixture was then treated with a solution of 2-aminothiazole (0.10 g, 1.01 mmol) and N,N-diisopropylethylamine (0.19 mL, 1.10 mmol) in tetrahydrofuran (2.3 mL). The reaction mixture was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh 80/20 hexanes/ethyl acetate) afforded 2-(4-benzyloxy-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (119.4 mg, 63.5%) as a white solid: mp 48-50° C.; EI-HRMS m/e calcd for C24H26N2O2S (M+) 406.1715, found 406.1716.

Workup

stirringThe reaction mixture was stirred at 25° C. for 18 h
concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-8d993246c61d450796d37c0a1cd389f7
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384220B2

Reaction notes

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