Water → HCID 178457811, compound

Participants

Reaction Conditions

Reaction Steps

To a RT suspension of (E)-4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-methoxy-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide (30 mg, 0.066 mmol) and sodium iodide (69.4 mg, 0.463 mmol) in ACN (0.6 mL) was added TMS-Cl (0.059 mL, 0.463 mmol) and water (10 μL), and the mixture was heated at 60° C. After 2 hours and 4 hours, additional TMS-Cl portions (0.059 mL, 0.463 mmol) were added, and the mixture was stirred at 60° C. for a total reaction time of 20 hours. The material was purified by reverse-phase preparative HPLC using 0.1% TFA in ACN/H2O, gradient 10% to 90% over 15 minutes. The combined fractions were freebased with saturated aqueous NaHCO3 and extracted with 10% IPA/DCM, dried over Na2SO4, filtered and evaporated. The title compound was obtained as a white solid (8 mg, 21% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (d, J=8 Hz, 6H) 1.50-1.60 (m, 2H) 1.62-1.82 (m, 2H) 2.05-2.08 (m, 2H) 2.49-2.51 (m, 1H) 2.55-2.74 (m, 2H) 3.97-4.02 (m, 1H) 4.60-4.70 (m, 1H) 6.38 (s, 1H) 7.20-7.30 (m, 2H) 7.48-7.52 (m, 1H) 7.64 (d, J=7.63 Hz, 1H) 8.29 (dd, J=8.22, 5.97 Hz, 2H) 11.10 (br. s., 1H) 12.26 (br. s., 1H). M/Z calc'd for C23H26FN5O3: 439.48. found 440 [M+H].

Provenance & Evidence