(+)-Glycidol → HCID 178488895, 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)-1-oxiranyl-methanol (14.0 mg, 1.5 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 lyophilized to afford the title compound as a white lyophilate (46 mg, 70%). 1H NMR (d-chloroform): 9.16 (br s, 1H), 8.03 (s, 1H), 7.65 (m, 2H), 7.30 (m, 1H), 7.02 (d, J=9 Hz, 1H), 6.95 (s, 1H), 6.32 (s, 1H), 6.17 (s, 1H), 5.52 (br m, 1H), 5.15 (m, 1H), 3.87 (m, 1H), 3.85 (s, 3H), 3.65-3.26 (m, 8H), 3.22-2.70 (m, 5H), 2.24 (d, J=9 Hz, 1H), 2.12 (m, 4H), 1.94 (m, 1H), 1.28 (s, 1H), 1.18 (d, J=5 Hz, 3H). MS: 567.17 (M+H). HPLC retention time: 1.91 minutes (G Method).

Provenance & Evidence