Dimethylformamide → HCID 57812467, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [4-(4-{6-amino-2-bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-furo[3,2-c]pyridin-3-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (20.0 mg, 0.0299 mmol), zinc cyanide (4.2 mg, 0.036 mmol) and Pd(PPh3)4 (3 mg, 0.003 mmol) in DMF (1 mL) was degassed and refilled with nitrogen (3×). The reaction was heated at 150° C. using a microwave reactor for 2 min. The solution was passed through a PL-Thiol SPE cartridge to remove metals. The material was then dissolved in dioxane and EtOH, charged with 4M HCl in Dioxane (0.2 mL) and stirred at rt for 4 h. The solution was concentrated in vacuo, redissolved in DMF (0.5 mL) and purified via HPLC. 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=1.93 (d, J=6.8 Hz, 3H), 2.30-2.40 (m, 4H), 3.18-3.26 (m, 2H), 3.59 (d, J=13.4 Hz, 2H), 4.64-4.71 (m, 1H), 6.43 (q, J=6.8 Hz, 1H), 7.21-7.27 (m, 1H), 7.42 (dd, J=9.0, 4.9 Hz, 1H), 8.11 (s, 1H), 8.33-8.39 (m, 2H). MS (ES+): m/z 515.06/517.07 (100/68) [MH+]. HPLC: tR=2.78 min (ZQ2, polar—5 min).

Provenance & Evidence