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

HRID 398567Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]([OH:12])=O)=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C)C=O.O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(4-cyano-phenyl)-3-cyclopentyl-propionic acid (33.0 mg, 0.13 mmol) in methylene chloride (1.36 mL) was cooled to 0° C. and then treated with a 2.0M solution of oxalyl chloride in methylene chloride (0.07 mL, 0.14 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 (30.0 mg, 0.29 mmol) and N,N-diisopropylethylamine (0.05 mL, 0.32 mmol) in tetrahydrofuran (0.67 mL). This solution was stirred at 25° C. for 3 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(4-cyano-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (44.1 mg, 100%) as a white solid: mp 64-66° C.; EI-HRMS m/e calcd for C18H19N3OS (M+) 325.1248 found 325.1247.

Workup

stirringThis solution was stirred at 25° C. for 3 h
concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-c661b2d3d1ec4746a1e8992930a08a3f
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610846B1

Reaction notes

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