N-(5-benzyloxy-pyridin-2-yl)-3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionamide → 3-cyclopentyl-2-(3,4-dichloro-phenyl)-N-(5-hydroxy-pyridin-2-yl)-propionamide

HRID 430187Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:32])[CH:17]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[CH:19]1([CH2:18][CH:17]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=2)=[O:32])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of N-(5-benzyloxy-pyridin-2-yl)-3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionamide (145.3 mg, 0.3 mmol) in methanol (5.1 mL) was treated with 10% palladium on activated carbon. The reaction mixture was stirred under hydrogen gas at 25° C. for 16 h. The catalyst was then filtered off through a pad of celite (ethyl acetate). The filtrate was concentrated in vacuo to give 3-cyclopentyl-2-(3,4-dichloro-phenyl)-N-(5-hydroxy-pyridin-2-yl)-propionamide (92.2 mg, 78.5%) as a tan solid: mp 79-81° C.; EI-HRMS m/e calcd for C19H20Cl2N2O2 (M+) 378.0896, found 378.0890.

Workup

filtrationThe catalyst was then filtered off through a pad of celite (ethyl acetate)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-802162639f95404f95b7e0f9bbfcdc30
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06320050B1

Reaction notes

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