Hydrochloric Acid → HCID 86732047, compound

Participants

Reaction Steps

To a stirred solution of trans-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl)pyrimidine-2-carbonitrile (21) (50.0 mg, 0.135 mmol, 1.0 eq.) in 1,4-dioxane (0.30 mL) was added concentrated HCl (0.30 mL, 3.6 mmol, 27 eq) at room temperature. The resulting mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was neutralized with saturated aqueous NaHCO3 and extracted with DCM (2×30 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulphate, and concentrated under reduced pressure. The resulting residue was purified by silica gel preparative TLC (5% methanol in dichloromethane) to afford trans-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl) pyrimidine-2-carboxamide (22) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 7.69 (m, 1H), 7.59 (br d, 1H, J=3.2 Hz), 7.33-7.21 (m, 3H), 6.44 (br d, 1H, J=3.2 Hz), 3.82 (s, 3H), 3.01 (m, 1H), 3.00 (s, 3H), 2.90 (m, 1H), 2.42 (s, 3H), 2.16-2.07 (m, 2H). LRMS m/z (M+H) 389 found, 389 required. m.p. 119-121° C.

Provenance & Evidence