3-Cyclopentyl-2-(4-nitro-phenyl)-N-thiazol-2-yl-propionamide → 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

HRID 966554Notes

Reaction equation

[CH:1]1([CH2:6][CH:7]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.[Pd]>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([CH:7]([CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-nitro-phenyl)-N-thiazol-2-yl-propionamide (prepared as in Example 22, 345 mg, 1.0 mmol) in ethyl acetate (100 mL) was treated with 10% palladium on activated carbon (34.5 mg). The reaction mixture was stirred under hydrogen gas at 60 psi at 25° C. for 6 h. The catalyst was then filtered off through a pad of celite, which was washed well with ethyl acetate. The resulting filtrate was concentrated in vacuo to give 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (288.3 mg, 91.4%) as a yellow solid: mp 102-107° C.; EI-HRMS m/e calcd for C17H21N3OS (M+) 315.1405, found 315.1401.

Workup

filtrationThe catalyst was then filtered off through a pad of celite, which
washwas washed well with ethyl acetate
concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-2519c42d90bc4b6ca0ecc74bc4ab072a
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951945B2

Reaction notes

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