Hydrochloric Acid → HCID 178508369, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-{1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-1H-pyrazol-4-yl}-2-chloro-furo[2,3-c]pyridin-7-ylamine (179 mg, 0.400 mmol), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3-benzothiadiazole (105.0 mg, 0.4006 mmol), Pd(PPh3)4 (46.3 mg, 0.0400 mmol), potassium carbonate (166 mg, 1.20 mmol) and 4:1 1,4-dioxane:water (6 mL) was heated in a microwave reactor at 110° C. for 1 h. Aqueous 12 N hydrochloric acid (0.5 mL, 6 mmol) and methanol (2 mL) were added, and the solution was heated to 30° C. for 30 min. The organic solvent was removed in vacuo, and the material was extracted with DCM and saturated aqueous sodium bicarbonate (2×). The organic layer was purified by column chromatography (1 to 3% 7 N ammonia/methanol:DCM), followed by trituration from methanol (5 mL) and filtration to afford 80 mg (50%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 1.31-1.46 (m, 2 H), 1.82-2.02 (m, 4 H), 2.04-2.15 (m, 2 H), 3.48-3.61 (m, 1 H), 4.14-4.25 (m, 1 H), 4.71 (d, J=4.5 Hz, 1 H), 6.42 (s, 2 H), 7.94-8.03 (m, 3 H), 8.06 (s, 1 H), 8.26 (s, 1 H), 8.65 (dd, J=7.5, 0.6 Hz, 1 H), 8.81-8.89 (m, 1 H); MS (ESI): 433.14 [M+H]+; HPLC tR=1.18 min (TOF: polar—3 min).

Provenance & Evidence