Hydrochloric Acid → HCID 178491827, 화합물

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A mixture of 3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (30.0 mg, 0.0696 mmol), 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-3,5-dimethyl-1H-pyrazole (60.5 mg, 0.139 mmol), Pd(PPh3)4 (4.02 mg, 0.00348 mmol), NaHCO3 (17.6 mg, 0.209 mmol) and 4:1 dioxane:water was heated to 80° C. overnight. 2 M of HCl in H2O (0.5 mL, 1 mmol) was added, and the solution was stirred at rt for 1 h. The material was concentrated in vacuo, redissolved in MeOH (1 mL) and passed through a syringe filter pad for HPLC purification. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.42-1.57 (m, 2H), 1.80 (d, J=7.1 Hz, 3H), 1.87-2.02 (m, 3H), 2.03 (s, 3H), 2.04-2.12 (m, 3H), 2.14 (s, 3H), 3.64 (br. s., 3H), 3.66-3.72 (m, 1H), 4.11 (tt, J=11.5, 3.9 Hz, 1H), 5.04-5.14 (m, 1H), 6.89 (dd, J=9.2, 4.2 Hz, 1H), 7.08 (t, J=8.8 Hz, 1H), 7.28 (s, 1H), 7.35 (d, J=1.3 Hz, 1H), 7.95 (br. s., 1H). MS (ES+): m/z=497.21/499.21 (100/50) [MH+]. HPLC: tR=1.40 min (polar—3 min, UPLC-ACQUITY).

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