1,2-Dichloroethane → [(2R)-2-(Cyclopentyl methyl)-3-(2-{5-fluoro-2-methyl-6-[(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Participants

Reaction Steps

5-Fluoro-4-hydrazino-2-methyl-6-[(1,3-thiazol-2-ylmethyl)amino]pyrimidine (80 mg, 0.33 mmol), (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (Hunigs base salt, 140 mg, 0.33 mmol), and HOAt (45 mg, 0.33 mmol) were dissolved in 3 mL of DMF. NMM (0.1 mL, 0.9 mmol) was added, followed by EDC (65 mg, 0.33 mmol). After stirring overnight at room temperature, the reaction mixture was purified by RP-HPLC to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (72 mg, 45%). LCMS: (M+H)+: 536.2.

Provenance & Evidence