1,2-Dichloroethane → HCID 86637008, compound

Participants

Reaction Steps

To a solution of 1-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N,5,5-tetramethyl-3-pyrrolidinamine (1.0502 g, 3.469 mmol) in DMF (16 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (1.0075 g, 3.299 mmol), N-methylmorpholine (1.8 mL, 16.37 mmol), 1-hydroxy-7-azabenzotriazole (0.540 g, 3.968 mmol), and EDC (0.760 g, 3.964 mmol). The solution was stirred overnight and then diluted with Et2O (100 mL). The mixture was washed with water (3×50 mL), and the combined aqueous phase was extracted with a fresh portion of Et2O (50 mL). This organic phase was washed with a fresh portion of water (25 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in DCM (150 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to provide crude [(2R)-3-(2-{2-chloro-6-[4-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (1.6539 g, 85% crude yield) as a dark red foam. LCMS: (M+H)+: 590.2.

Provenance & Evidence