Sodium Bicarbonate → HCID 178509142, compound

Participants

Reaction Steps

A solution of 5-phenyl-6-(4-{[4-(5-pyridin-4-yl-1H-pyrazol-3-yl)piperidin-1-yl]methyl}phenyl)nicotinonitrile (4B-5; 0.030 g, 0.060 mmol) and thiosemicarbazide (0.006 g, 0.066 mmol) in TFA (1.5 mL) were 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 (4B-6) 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+0.01% TFA). 1H-NMR (500 MHz, d6 DMSO) δ 13.54 (bs, 1H), 9.64 (s, 1H), 9.07 (d, J=1.96, 1H), 8.81 (d, J=6.11, 2H), 8.21 (s, 2H), 8.10 (d, J=2.2, 1H), 7.65 (s, 2H), 7.23-7.49 (m, 9H), 7.00 (s, 1H), 4.33 (d, 2H), 3.45 (d, J=10.5, 2H), 2.95-3.15 (m, 3H), 2.21 (d, J=12.69, 2H), 1.76-1.90 (m 2H). HRMS m/z (M+H) Calcd: 571.2387, found: 571.2359.

Provenance & Evidence