Dichloromethane → HCID 131728078, compound

Participants

Reaction Steps

To a solution of methanesulfonic acid 3-(7-cyano-1-cyclohexylmethyl-1H-indol-3-yl)-[1,2,4]thiadiazol-5-ylmethyl ester (120 mg, 0.28 mmol) in dichloromethane (3 ml) was added pyrrolidine (0.12 ml, 1.4 mmol) and the reaction subjected to microwave irradiation at 100° C. for 5 minutes. The reaction was purified directly by flash column chromatography eluting with dichloromethane then 25-50% (v/v) ethyl acetate in heptane to afford the title compound (71 mg, 0.175 mmol) as the free base. The free base (35 mg, 0.086 mmol) was dissolved in dichloromethane (2 ml) and hydrogen chloride (1M solution in diethyl ether) was added. The mixture was concentrated in vacuo to afford the title compound as a 1:1 hydrochloride salt. 1H NMR (400 MHz, CD3OD): 1.06-1.36 (7H, m), 1.62-1.80 (5H, m), 1.91-2.07 (1H, m), 2.09-2.34 (2H, br m), 3.35-4.20 (4H, br m), 4.42 (2H, d, J 7), 5.07 (2H, s), 7.37 (1H, t, J 8), 7.69 (1H, dd, J 7, 1), 8.23 (1H, s); 8.84 (1H, dd, J 8, 1) EsIMS: m/z 406.4 [M+H]+.

Provenance & Evidence