2-Aminothiazole → 3-cyclopentyl-2-(nitrophenyl)-N-thiazol-2-yl-propionamide

HRID 430106Notes

Reaction equation

C1(CC([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)C(O)=O)CCCC1.[C:20](Cl)(=[O:24])[C:21](Cl)=O.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1.C(N(CC)[CH:36]([CH3:38])[CH3:37])(C)C.O1C[CH2:44][CH2:43][CH2:42]1>C(Cl)Cl.CN(C)C=O>[CH:36]1([CH2:37][CH:21]([C:12]2[CH:11]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:17]([O-:19])=[O:18])[C:20]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:24])[CH2:38][CH2:44][CH2:43][CH2:42]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(3-nitro-phenyl)-propionic acid (432 mg, 1.64 mmol) in methylene chloride (16 mL) was cooled to 0° C. and then treated with a 2.0 M solution of oxalyl chloride in methylene chloride (0.90 mL, 1.80 mmol) and a few drops of N,N-dimethylformamide. The reaction mixture was stirred at 0° C. for 15 min and at 25° C. for 1.2 h. The reaction mixture was then treated with a solution of 2-aminothiazole (361.4 mg, 3.61 mmol) in tetrahydrofuran (16 mL) and N,N-diisopropylethylamine (0.70 mL, 3.93 mmol). The reaction mixture was stirred at 25° C. for 6 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh 70/30 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(nitrophenyl)-N-thiazol-2-yl-propionamide (409.3 mg, 72.2%) as a tan solid: mp 171-174° C.; EI-HRMS m/e calcd for C17H19N3O3S (M+) 345.1147, found 345.1153.

Workup

stirringThe reaction mixture was stirred at 25° C. for 6 h
concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-7a1f078a06cb4faf96e4655626ffac4f
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06320050B1

Reaction notes

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