Hydrochloric Acid → HCID 178518664, compound

Participants

Reaction Conditions

Reaction Steps

6-(4-(4H-1,2,4-triazol-3-yl)phenyl)-1-(2-(piperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride. Ethyl 4-(2-oxo-3-(2-(piperidin-1-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzimidate hydrochloride (0.4 g., 1.01 mmol), formic hydrazide (0.183 g., 3.04 mmol) and triethylamine (0.42 mL, 3.04 mmol) were combined in methanol (4 mL) and heated in a sealed tube at 100° C. for 3 h. The reaction mixture was cooled to room temperature and purified by reverse-phase semi-preparatory HPLC (5-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). The clean fractions were collected and concentrated and the solid obtained was treated with hydrochloric acid in ether, filtered and dried under high vacuum to yield the title compound (0.035 g., 8.1% yield). 1H NMR (400 MHz, DMSO-d6+D2O) δ 8.64 (s, 1H), 8.50(s, 1H), 8.20 (d, J=8.4, 2H), 8.15 (d, J=8.4, 2H), 4.34 (m, 2H), 3.76 (d, J=10.8, 2H), 3.53 (m, 2H), 2.98 (t, J=10.8, 2H), 1.86 (m, 2H),1.70 (m, 2H), 1.5 (m, 2H); MS (ESI) m/z 391.5[M+1]+; mp 194-197° C.

Provenance & Evidence