Hydrochloric Acid → HCID 72943390, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (Example-31) (200 mg, 0.351 mmol) in methanol (5 ml) added saturated HCl in methanol at 0° C. This gradually brought to RT and stirred for four hours. Reaction mass was cooled and added ether to get solids. Solvents decanted and solids washed by ethyl acetate and dried. This residue was made free base using saturated sodium carbonate. This afforded 16.0 mg (9.75% yield) of titled compound after purification by preparative TLC (SiO2 using 3% methanol in chloroform as eluent). 1H NMR (CD3OD, 300 MHz): δ 8.557-8.550 (d, 1H), 8.192-8.184 (d, 1H), 7.866 (s, 1H), 7.762 (s, 1H), 7.446-7.360 (m, 2H), 7.160-7.10 (m, 2H), 7.05-6.85 (m, 3H), 5.420 (s, 2H), 3.276-3.242 (m, 4H), 3.119-3.086 (m, 4H). MS: m/z=470.9 (M+1); HPLC: 97.41% in method A.

Provenance & Evidence