(R)-1,2-Epoxypropane → HCID 178488909, compound

Participants

Reaction Steps

(1S,2S,3R,4R)-3-[6-Chloro-2-(4-methoxy-2-piperidin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (Compound XXX) (60 mg, 0.1 mmol) was stirred with (R)-propylene oxide (8.0 mg, 1.0 mmol) in methanol (5 mL) in a sealed tube overnight. The reaction was concentrated and the product purified by reverse phase chromatography (Gilson). Desired fractions were collected, combined, and neutralized by partitioning between dichloromethane and saturated sodium bicarbonate solution. The organic layer was separated, dried (magnesium sulfate) and concentrated to afford the title compound as a white solid 9 mg, 10%). 1H NMR (d-chloroform): 13.83 (br s, 1H), 7.89 (s, 1H), 7.66 (d, J=8 Hz, 1H), 7.07 (s, 1H), 6.97 (d, J=8 Hz, 1H), 6.32-6.28 (m, 3H), 5.62 (m, 1H), 5.22 (m, 2H), 3.95 (s, 3H), 3.87 (m, 1H), 3.70 (m, 1H), 3.15 (s, 1H), 3.07 (m, 1H), 2.93 (m, 2H), 2.74 (d, J=7 Hz, 1H), 2.36 (m, 4H), 1.99 (m, 3H), 1.76 (m, 3H), 1.28 (s, 1H), 1.18 (d, J=5 Hz, 3H). MS: 551.18 (M+H). HPLC retention time: 1.99 minutes (G Method).

Provenance & Evidence