Hydrazine → N-(4-(3-Amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)phenyl)acetamide

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Reaction Conditions

Reaction Steps

A mixture of N-(4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)phenyl)acetamide (24.9 mg, 0.057 mmol), 35% aqueous hydrazine (20 μL, 0.637 mmol) and N,N-dimethylformamide (0.5 mL) in a sealed tube was heated to 100° C. for 3 h, 120° C. for 6 h and concentrated. Silica gel chromatography, eluting with 0-10% methanol in dichloromethane, gave the desired product. The material was triturated with dichloromethane and filtered to give Example 200 as light yellow solid (9.4 mg, 38% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.20 (1H, s), 10.08 (1H, s), 8.11 (2H, δ, J=8.78 Hz), 7.81-7.84 (2H, m), 7.69 (2H, δ, J=8.78 Hz), 7.63 (1H, s), 7.43-7.48 (2H, m), 7.13-7.23 (5H, m), 4.83 (2H, s), 2.07 (3H, s); MS (ES+) m/z: 436 (M+H); LC retention time: 3.200 min (analytical HPLC Method A).

Provenance & Evidence