1,2-Dichloroethane → HCID 86636953, compound

Participants

Reaction Steps

To a solution of 4-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-6-hydrazino-2-methylpyrimidine (8.04 g, assumed 31.4 mmol) in N,N-dimethylformamide (125 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid diisopropylethylamine salt, isopropanol solvate (15.48 g, 31.3 mmol), N-methylmorpholine (17.21 mL, 156 mmol), 1-hydroxy-7-azabenzotriazole (5.11 g, 37.6 mmol), and EDC (7.20 g, 37.6 mmol). The solution was stirred overnight, and then diluted with Et2O (150 mL) and washed with water (2×100 mL). The combined aqueous phase was extracted with a fresh portion of Et2O (150 mL), and this organic phase was washed with water (75 mL). The total combined aqueous phase was extracted with another fresh portion of Et2O (150 mL), and this organic phase was washed with water (75 mL). The combined organic phase was diluted with DCM (100 mL), and dried over anhydrous Na2SO4. The mixture was filtered and concentrated in vacuo to give crude [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (15.60 g, 28.8 mmol, 92% yield) as a light brown foam. LCMS: (M+H)+: 541.7.

Provenance & Evidence