Piperidine → HCID 67306163, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-(7-methoxy-3-(2-((3-methoxybenzyl)amino)pyrimidin-4-yl)naphthalen-1-yl)piperazin-1-yl)propan-1-ol (65 mg, 0.127 mmol) and triethlyamine (35 μl, 0.254 mmol) in dichloromethane (2 ml) was treated with methanesulfonyl chloride (10 μl, 0.133 mmol) and stirred for one hour. The mixture was diluted with water (2 ml), the organic layer removed and the aqueous layer extracted with dichloromethane (2 ml). The organic layer was concentrated under reduced pressure. The product was treated with acetonitrile (2 ml) and treated with piperidine (38 μl, 0.381 mmol) and heated to 50° C. for 1 hour then concentrated under reduced pressure. The mixture was diluted with saturated aqueous sodium bicarbonate (10 ml) and extracted with dichloromethane (3×10 ml). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure and purified by flash column chromatography using a gradient of methanol-dichloromethane as eluent to afford 4-(6-methoxy-4-(4-(3-(piperidin-1-yl)propyl)piperazin-1-yl)naphthalen-2-yl)-N-(3-methoxybenzyl)pyrimidin-2-amine (194) (18 mg). M.p.=63-75° C.; 400 M Hz 1H NMR (DMSO-d6) δ: 8.35 (d, J=5.2 Hz, 1H), 8.30 (s, 1H), 7.94 (d, J=9.2 Hz, 1H), 7.81 (bm, 2H), 7.42 (s, 1H), 7.23 (m, 3H), 6.99 (bm, 2H), 6.78 (dd, J=2.0 and 8.4 Hz, 1H), 4.55 (d, J=6.4 Hz, 2H), 3.91 (s, 3H), 3.71 (s, 3H), 3.40-2.40 (m, 16H), 1.73 (bm, 2H), 1.57 (bm, 4H), 1.44 (bm, 2H); LCMS: 581 [M+H+].

Provenance & Evidence