Hydrochloric Acid → HCID 67003539, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with tert-butyl 3-(5-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)-3-(methoxymethoxy)azetidine-1-carboxylate (Example 54B) (500 mg, 0.849 mmol), methanol (6.5 mL) and aqueous 2 molar HCl solution (2.58 mL, 8.49 mmol). The reaction mixture was heated to 60° C. for 5 hours, then 35° C. overnight. The reaction mixture was cooled to room temperature and diluted with saturated aqueous brine solution and ethyl acetate. The layers were separated, and the aqueous layer extracted with ethyl acetate (3×20 mL). The organic layers were combined and concentrated. The remaining solid was triturated with water (pH approximately 10). The solids were collected by vacuum filtration, washed with water, and dried at low temperature in a vacuum oven to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (d, 1H), 8.40 (s, 1H), 8.10 (d, 1H), 8.01 (d, 2H), 7.44 (d, 2H), 7.14 (d, 1H), 7.06 (s, 1H), 3.96 (d, 2H), 3.71 (d, 2H), 2.35 (s, 3H); MS APCI(+) m/z 445.22 (M+H)+.

Provenance & Evidence