Triethylamine → HCID 87085130, compound

Participants

Reaction Conditions

Reaction Steps

4-Dimethylaminopyridine (81 mg, 0.66 mmol, 1.5 equiv) and methyl chlorothiolformate (50 μL, 0.57 mmol, 1.3 equiv) were sequentially added to a stirred suspension of N-methyl-5-(pyridin-3-yl)-1,3,4-thiadiazol-2-amine (85 mg, 0.44 mmol, 1.0 equiv) in dichloroethane (3.4 mL) at 23° C. The resulting solution was heated to 75° C. and stirred for 72 h. The cooled reaction mixture was directly subjected to silica gel column chromatography (55% ethyl acetate in hexane spiked with 5% triethylamine) to afford the title compound as an off-white powder (100 mg, 83%): mp 192-194° C.; IR (KBr thin film) 2931 (w), 1727 (w), 1634 (s), 1570 (w) cm−1; 1H NMR (300 MHz, CDCl3) δ 9.13 (d, J=2 Hz, 1H), 8.70 (dd, J=5, 2 Hz, 1H), 8.28 (dt, J=8, 2 Hz, 1H), 7.43 (dd, J=8, 5 Hz, 1H), 3.86 (s, 3H), 2.53 (s, 3H); ESIMS m/z 267 ([M+H]+). Compound 87 was prepared as described in Example 15.

Provenance & Evidence