Piperidine → HCID 57780682, compound

Participants

Reaction Steps

To a suspension of methanesulfonic acid 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-5,6,7,8-tetrahydro-quinazolin-8-yl ester (76 mg, 0.18 mmol) in dimethylformamide (2 mL) was added under nitrogen at 0° C. piperidine (30 mg, 0.35 mmol) and triethyl amine (36 mg, 0.35 mmol). The reaction was stirred at room temperature over night. Piperidine (30 mg, 0.35 mmol) was added and the reaction stirred at room temperature for 3 hours. The reaction was diluted with water and extracted twice with diethyl ether. The combined organic layers were washed with dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel using dichloromethane/methanol/concentrated aqueous ammonia (19:1:0.2 v/v/v) as eluent to yield the title compound (13 mg, 18%) as an orange solid. MS ISP (m/e): 334.3 (27), 419.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.60 (s, 1H), 8.26 (s, 1H), 7.82 (s, 1H), 7.65 (s, 1H), 7.60 (d, 1H), 7.19 (d, 1H), 7.03 (s, 1H), 3.80 (s, 3H), 3.63 (m, 1H), 3.05 (m, 1H), 2.55-2.80 (m, 2H), 2.25 (m, 2H), 2.14 (s, 3H), 1.89 (m, 2H), 1.38-1.68 (m, 8H).

Provenance & Evidence