1,2-Dichloroethane → (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(6-ethyl-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Participants

Reaction Steps

To a solution of (3R)-3-(cyclopentylmethyl)-4-(5-{[(6-ethyl-2-pyridinyl)amino]carbonyl}-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoic acid (314 mg, 0.79 mmol) in dichloromethane (DCM) (10 mL) was added N-methylmorpholine (0.22 mL, 2.04 mmol), O-(phenylmethyl)hydroxylamine hydrochloride (188 mg, 1.18 mmol), EDC (181 mg, 0.94 mmol) and 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (107 mg, 0.79 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The reaction mixture was then washed with water (5 mL) and NaHCO3 solution (5 mL×3), and concentrated to provide the crude product as a mixture of diastereomers. This mixture was purified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-65% MeCN:H2O) to afford (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(6-ethyl-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (157 mg, 39% yield). MS: 506 ([M+H]+).

Provenance & Evidence