Hydrochloric Acid → HCID 178508372, compound

Participants

Reaction Steps

A solution of 4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]-2-chlorofuro[2,3-c]pyridin-7-amine (70.5 mg, 0.158 mmol), (6-fluoro-1,3-benzothiazol-7-yl)boronic acid (44.0 mg, 0.22 mmol), and Pd(PPh3)4 (18.2 mg, 0.0158 mmol) in 1,4-dioxane (1.23 mL) and aqueous 1.0 N sodium carbonate solution (0.615 mL, 0.615 mmol) was heated to 120° C. in a microwave for 60 min. Into the reaction mixture was added hydrochloric acid in 1,4-dioxane (4 N in 1,4-dioxane, 0.59 mL, 2.36 mmol), and the reaction mixture was stirred at rt for 30 min, then purified by MDPS to afford 4.4 mg (6%) of the title compound as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 9.63 (s, 1H), 8.23 (s, 1H), 8.21 (s, 1H), 8.18 (s, 1H), 8.16 (s, 1H), 7.91 (s, 1H), 7.81 (s, 1H), 6.52 (brs, 2H), 4.67 (brd, J=3.2 Hz, 1H), 4.21 (tt, J=11.4, 4.0 Hz, 1H), 3.55-3.45 (m, 1H), 2.08-2.02 (m, 2H), 1.97-1.78 (m, 4H), 1.44-1.30 (m, 2H); MS (ESI): 450.03 [M+H]+; HPLC: tR=2.85 min (ZQ3: polar—5 min).

Provenance & Evidence