Hydrochloric Acid → HCID 136508842, compound

Participants

Reaction Steps

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[6-methoxy-2-(morpholin-4-yl)-5-[7-(trifluoromethyl)-1,3-benzothiazol-2-yl]pyrimidin-4-yl]amino]piperidine-1-carboxylate (40.0 mg, 0.07 mmol, 1.00 equiv) and conce. hydrochloric acid (3.0 mL). The crude product was triturated in methanol and dissolved in 5.0 ml of water. The pH value of the solution was adjusted to 11 with sodium hydroxide (1 M). The solid was collected by filtration and dried in vacuo to afford the title compound. Yield: 16.1 mg (50%). 1H-NMR (400 MHz, DMSO-d6): ppm 1.54-1.57(m, 1H), 1.63-1.73(m, 2H), 1.94(m, 1H), 2.64-2.82(m, 3H), 3.08-3.11(m, 1H), 3.69-3.70(m, 8H), 4.17-4.18(m, 1H), 7.57-7.63(m, 2H), 8.00-8.02(d, J=7.6 Hz, 1H), 10.69-10.71(m, 1H); 19F-NMR (300 MHz, DMSO-d6): ppm −61.57; MS m/z [M+H]+ (ESI): 481. IRAK4 IC50=520 nM

Provenance & Evidence