1,2-Dichloroethane → [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[7-(dimethylamino)-5-azaspiro[2.4]hept-5-yl]-2-ethyl-5-fluoro-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide

Participants

Reaction Steps

To a solution of racemic 5-(2-ethyl-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N-dimethyl-5-azaspiro[2.4]heptan-7-amine (0.0818 g, 0.278 mmol) in DMF (3 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.0778 g, 0.255 mmol), N-methylmorpholine (0.140 mL, 1.273 mmol), 1-hydroxy-7-azabenzotriazole (42 mg, 0.309 mmol), and EDC (59 mg, 0.308 mmol). The solution was stirred overnight and then purified directly by Gilson RPLC to give [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[7-(dimethylamino)-5-azaspiro[2.4]hept-5-yl]-2-ethyl-5-fluoro-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1058 g, 71% yield, mixture of diastereomers) as a yellow oil. LCMS: (M+H)+: 582.3.

Provenance & Evidence