Hydrochloric Acid → HCID 178518640, compound

Participants

Reaction Steps

To a 50-mL round-bottomed flask with N-(cis-3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)benzo[d]thiazol-2-amine (example 9, 100 mg, 0.285 mmol) was added hydrogen chloride (1 M in diethyl ether, 1.0 mL, 1.0 mmol). The solution was stirred for minutes then concentrated under reduced pressure. The crude was diluted with saturated sodium bicarbonate solution and extracted with dichloromethane (10 mL). The organic extract was dried over sodium sulfate then concentrated in vacuo to give the crude material as a off-white oil. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (4 g, hexane to ethyl acetate gradient) to provide 3-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (40 mg, 0.119 mmol, 83% yield) as light-yellow solid. M+1: 338. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.67-2.80 (m, 2 H) 3.02-3.16 (m, 2 H) 4.12-4.26 (m, 1 H) 4.62-4.77 (m, 1 H) 6.93-7.10 (m, 2 H) 7.22 (td, J=7.20, 1.30 Hz, 1 H) 7.30 (dd, J=7.75, 1.32 Hz, 1 H) 7.37-7.43 (m, 1 H) 7.67 (dd, J=7.75, 0.73 Hz, 1 H) 7.98 (dd, J=5.19, 1.39 Hz, 1 H) 8.50 (d, J=6.72 Hz, 1 H).

Provenance & Evidence