Hydrochloric Acid → 2-(morpholin-4-yl)-6-[[(3R)-piperidin-3-yl]amino]-5-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]-3,4-dihydropyrimidin-4-one

Participants

Reaction Conditions

Reaction Steps

(3R)-tert-butyl 3-(6-methoxy-2-morpholino-5-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)pyrimidin-4-ylamino)piperidine-1-carboxylate (40.0 mg, 0.07 mmol, 1.00 equiv) was added to concentrated hydrochloric acid (3.0 mL, 12N). The resulting solution was stirred for 2 h at 80° C. in an oil bath. After concentrated under reducing pressure, the residue was washed with 30 mL of methanol. The solid was collected by filtration and dissolved in 5 ml of water. After adjusted the pH value to 11 with 1N sodium hydroxide (aq.), the solid was collected by filtration and dried in vacuo to provide the title compound as a yellow solid. 1H-NMR (400 MHz, DMSO-d6): δ ppm 1.58-1.86(m, 3H), 1.95-1.96(m, 1H), 2.58-2.67(m, 2H), 2.78-2.81(m, 1H), 3.11-3.13(m, 1H), 3.65-3.67 (m, 8H), 4.08-4.12(m, 1H), 7.445-7.466(d, J=8.4 Hz, 1H), 7.943-7.980(d, J=14.8 Hz, 1H), 8.072-8.092 (d, J=8.0 Hz, 1H), 10.347-10.364(m, 1H); MS m/z [M+H]+ (ESI): 481. IRAK4 IC50=70 nM

Provenance & Evidence