1-Methylimidazole → (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-4-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

1-Methylimidazole (39.7 μl, 0.498 mmol) was added into the solution of (55)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (100 mg, 0.249 mmol) in N,N-dimethylformamide (DMF) (1.8 ml). The resulting solution was cooled to 0° C., and then mesyl chloride (20.24 μl, 0.262 mmol) was added dropwise at 0° C. To the reaction mixture was added 4-pyrimidinamine (26.1 mg, 0.274 mmol). After stirring for 2 h 10 min at ambient temperature, the reaction solution was purified by RP-HPLC to yield (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-4-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide (76 mg, 0.159 mmol, 64% yield). MS (ES+) m/z 478.8 (MH+).

Provenance & Evidence