Sodium Bicarbonate → HCID 11365019, compound

Participants

Reaction Steps

A solution of 6-(4-{[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (4A-4; 0.035 g, 0.072 mmol) and thiosemicarbazide (0.010 g, 0.108 mmol) in TFA (2 mL) was heated to 60° C. for 16 hr. The reaction was then cooled, poured onto ice, and basified with saturated aqueous sodium bicarbonate. The resulting precipitate was filtered, taken up in DMF and purified by reverse phase HPLC (5% CH3CN: 95% H2O+0.1% TFA to 95% CH3—CN: 5% H2O+0.1% TFA). 1H-NMR (500 MHz, d6 DMSO) δ 9.72 (bs, 1H), 9.07 (d, J=2.19, 1H), 8.93 (bs, 1H), 8.42 (bs, 1H), 8.36 (s, 1H), 8.29 (s, 1H), 8.10 (d, J=1.96, 1H), 7.65 (bs, 2H), 7.22-7.49 (m, 9H), 4.93-5.03 (m, 1H), 4.34 (s, 2H), 3.49 (d, J=12.21, 2H), 3.19-3.35 (m, 2H), 2.32-2.56 (m, 2H), 2.15 (d, J=11.96, 2H). HRMS m/z (M+H) Calcd: 561.2292, found: 561.2256.

Provenance & Evidence