Acetic Acid → HCID 178521029, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 6-(trifluoromethyl)picolinimidate (291 mg, 1.3 mmol) and triethylamine (0.6 mL, 4.4 mmol) in ethanol (5 mL) was added dropwise a solution of (R)-(1-(4,5-diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (400 mg, 1.1 mmol) and acetic acid (0.3 mL, 6.6 mmol) in ethanol (10 mL) at room temperature over a period of 10 min. The reaction mixture was stirred for 16 h at 120° C. The mixture was concentrated and the residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound (110 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ 1.18-1.32 (m, 1H), 1.48 (d, 1H), 1.71 (t, 2H), 1.76-1.83 (m, 2H), 1.89 (dt, 3H), 2.55-2.64 (m, 2H), 2.85-3.03 (m, 2H), 3.42-3.50 (m, 1H), 3.51-3.63 (m, 1H), 4.76 (d, 2H), 8.00 (d, 1H), 8.22-8.32 (m, 1H), 8.49 (d, 1H), 8.83 (br s, 1H), 13.41 (br s, 1H). MS (ES+) (M+H) 446.33; LCMS retention time 3.34 min (Method S).

Provenance & Evidence