Pyridine → HCID 178493029, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-7-(1S,4S)-2,5-diaza-bicyclo[2.2.1]hept-2-yl-2-(2-methoxy-4-morpholin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridine hydrochloride (Compound XXXVII) (50 mg, 0.1 mmol), (S)-2-methyl-oxirane (7.30 mg, 0.126 mmol), pyridine (10.2 μL, 0.126 mmol), and methanol (3.0 mL) were stirred in a sealed tube at room temperature overnight. An additional equivalent each of epoxide and Hunig's base were added and the mixture was heated at 80° C. overnight. The mixture was concentrated and the material was subjected to purification via reverse phase chromatography (Gilson) to afford the title compound as a yellow lyophilate (26 mg, 50%). 1H NMR (d-chloroform): 13.63 (br s, 1H), 8.10 (m, 1H), 7.90 (s, 1H), 7.71 (s, 1H), 7.55 (s, 1H), 6.59 (m, 1H), 6.46 (s, 1H), 4.62 (m, 1H), 4.35 (m, 1H), 4.24 (t, J=7 Hz, 2H), 4.15 (s, 3H), 3.92 (s, 4H), 3.35 (s, 4H), 3.14 (m, 2H), 2.38 (m, 1H), 1.71 (m, 1H), 1.44 (m, 2H), 1.32 (m, 1H), 0.94 (m, 3H). MS: 499.18 (M+H). HPLC retention time: 1.83 minutes (G Method).

Provenance & Evidence