Hydrazine → HCID 69670471, compound

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Reaction Steps

A solution of methyl 4-(3-amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)benzoate (28 mg, 0.064 mmol, from Example 192) and hydrazine (20 μL 0.637 mmol) in N,N-dimethylformamide (0.5 mL) was stirred at 100° C. for 3 h. LC-MS showed that only small amount of the desired product was formed. A 35% aqueous solution of hydrazine (0.5 mL) was added. After additional 1 h at 100° C., the mixture was cooled to give a suspension. Water was added and the mixture filtered. The solid was washed with water, dried under vacuum to give Example 194 (19 mg, 67% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 8.18 (2H, δ, J=8.53 Hz), 7.91 (2H, δ, J=8.53 Hz), 7.81-7.85 (2H, m), 7.71 (1H, s), 7.42 (2H, t, J=8.03 Hz), 7.16-7.22 (3H, m), 7.13 (2H, dd, J=8.66, 1.13 Hz); MS (ES+) m/z: 437 (M+H); LC retention time: 2.801 min (analytical HPLC Method A).

Provenance & Evidence