Isopropylamine → HCID 24803615, compound

Participants

Reaction Steps

A 35 mL scintillation vial was charged with 4-chloro-N-(5-chloro-2-(hydrazinecarbonyl)pyridine-3-yl)-3-(trifluoromethyl)benzenesulfonamide (500 mg, 1.1 mmol), cyanogenbromide (200 mg, 2.0 mmol) anhydrous MeCN (5 mL). The resultant mixture was heated to 65° C. and stirred for 2 h. After cooling to room temperature, isopropylamine (500 mg, 8.2 mmol) was added followed by AcOH (0.5 mL) and the mixture was heated to 135° C. and stirred for 2 h. After cooling to room temperature, reaction mixture was concentrated under reduced pressure. The residue was further purified through automated normal-phase chromatography (10% to 100% gradient of EtOAc-Hexane) and followed by preparative HPLC (10% to 90% gradient of MeCN-water) and dried (Lyophilizer) to afford the title compound. 1H NMR (400 MHz, CDCl3) 8.28 (d, 1H), 8.18 (d, 1H), 8.10 (d, 1H), 7.90 (dd, 1H), 7.58 (d. 1H), 4.32 (br, 1H), 3.88 (m, 1H), 1.34 (d (d, 6H). MS (ES) [M+H]+ expected 495.0, found 495.0.

Provenance & Evidence