1,2-Dichloroethane → [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1-methylethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

Participants

Reaction Steps

A mixture of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (268 mg, 0.88 mmol), 2-chloro-5-fluoro-6-hydrazino-N-(1-methylethyl)-4-pyrimidinamine (assumed 253 mg of free base, 0.97 mmol), EDC (186 mg, 0.97 mmol), HOAt (132 mg, 0.97 mmol), and NMM (0.64 mL, 5.82 mmol) in DMF was stirred at room temperature overnight. The reaction mixture was then purified via reverse phase HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1-methylethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (74 mg, 17%). LCMS: (M+H)+: 507.1.

Provenance & Evidence