Sodium Chloride → HCID 10236928, compound

Participants

Reaction Steps

4-Morpholinecarbonyl chloride (0.250 mL, 2.14 mmol) was added drop wise to a slurry of 1-(4-aminobutyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (0.500 g, 2.14 mmol) in chloroform (10 mL). After 1 hour, analysis by high performance liquid chromatography showed about 60% completion. 4-Morpholinecarbonyl chloride (0.200 mL) was added and the reaction mixture was stirred overnight. The reaction mixture was poured into 5% sodium hydroxide and stirred for 10 minutes. The layers were separated. The aqueous layer was extracted with chloroform (×2). The combined organics were washed with water and brine then dried over magnesium sulfate and concentrated under reduced pressure to provide a yellow oil. The aqueous layer was saturated with sodium chloride and then extracted with dichloromethane (×3). The extracts were combined, dried and then combined with the yellow oil and concentrated under reduced pressure. The residue was purified by column chromatography (43 g of silica gel eluting with 2% methanol in dichloromethane containing 1% triethylamrine and then with 5% methanol in dichloromethane containing 1% triethylamine). The residue was dissolved in dichloromethane and the solution was diluted with hexanes. The resulting precipitate was isolated by filtration and then recrystallized twice from acetonitrile to provide 0.283 g of N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]morpholine-4-carboxamide as a pale yellow powder, m.p. 163.7-167.0° C. Analysis: Calculated for C17H26N6O2: %C, 58.94; %H, 7.56; %N, 24.26; Found: %C, 58.66; %H, 7.69; %N, 24.22. 1H NMR (300 MHz, DMSO-d6) δ7.91 (s, 1H), 6.51 (t, J=5.5 Hz, 1H), 5.73 (s, 2 H), 4.29 (t, J=7.1 Hz, 2 H), 3.51 (t, J=4.8 Hz, 4 H), 3.20 (t, J=4.8 Hz, 4 H), 3.04 (q, J=6.8 Hz, 2 H), 2.36 (s, 3 H), 2.30 (s, 3 H), 1.70 (quintet, J=7.4 Hz, 2 H), 1.35 (quintet, J=7.4 Hz, 2 H); MS (CI) m/e 347.2197 (347.2195 calcd for C17H26N6O2, M+H).

Provenance & Evidence