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 (323 mg, 0.81 mmol) in dichloromethane (DCM) (10 ml) was added O-(phenylmethyl)hydroxylamine (129 mg, 1.05 mmol), 4-methylmorpholine (0.23 ml, 2.1 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (110 mg, 0.81 mmol), and EDC (186 mg, 0.97 mmol) at 0° C. The reaction was left to warm to room temperature and stirred overnight. The reaction was then washed with water (15 mL) and NaHCO3 solution (15 mL×3), then concentrated to provide the crude product as a mixture of diastereomers, which 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 (119 mg, 29% yield). MS: 506 ([M+H]+).

Provenance & Evidence