Hydrochloric Acid → (R)-5-(7-chlorobenzo[d]thiazol-2-yl)-2-morpholino-6-(piperidin-3-ylamino)pyrimidin-4(3H)-one

Participants

Reaction Steps

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[5-(7-chloro-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (40.0 mg, 0.07 mmol, 1.00 equiv) and 12 N hydrochloric acid (3.0 ml). The solid was collected by filtration and dried in vacuo to give the title compound as an off-white solid. 1H-NMR (400 MHz, DMSO-d6): ppm 1.611-1.736(m, 3H), 1.935(m, 1H), 2.621-2.819(m, 3H), 3.079-3.114(m, 1H), 3.687-3.698(m, 8H), 4.157-4.167(m, 1H), 7.306-7.325(d, J=7.6 Hz, 1H), 7.399-7.419(d, J=8.0 Hz, 1H), 7.686-7.706(d, J=8.0 Hz, 1H), 10.667-10.685(m, 1H). MS m/z [M+H]+ (ESI): 447. IRAK4 IC50=180 nM

Provenance & Evidence