Triethylamine → HCID 44553731, compound

Participants

Reaction Steps

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl}benzohydrazide (Step 1 of Example 48, 50 mg, 0.115 mmol) and 1,1′-carbonothioylbis(1H-imidazole) (41 mg, 0.23 mmol) in dichloromethane (1 mL) was added triethylamine (46 mg, 0.46 mmol) at rt. After 1 h, the reaction was quenched with aq NaHCO3 and the product was extracted 3 times with EtOAc. The combined extracts were concentrated, and the residue was subjected to reverse phase HPLC. The fractions containing the product were collected and concentrated. The residue was diluted with EtOAc, washed with aq NaHCO3, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford the title compound. 1H NMR (500 MHz, (CDCl3): 8.65 (d, 1H), 8.38 (broad d, 1H), 8.36 (d, 2H), 8.19 (s, 1H), 8.03 (d, 2H), 7.84 (m, 1H), 7.38 (m, 1H), 7.27 (d, 2H), 7.07 (d, 2H), 4.16 (s, 3H). LCMS: m/z 478 (M+H)+.

Provenance & Evidence