Hydrochloric Acid → 2-[2-(morpholin-4-yl)-6-oxo-4-[[(3R)-piperidin-3-yl]amino]-1,6-dihydropyrimidin-5-yl]-1,3-benzothiazole-5-carboxamide

Participants

Reaction Steps

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[5-(5-carbamoyl-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (70.0 mg, 0.12 mmol, 1.00 equiv) and cone. hydrochloric acid (4.0 mL). The crude product was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001(SHIMADZU)): Column, XBridge Shield RP18 OBD Column, 5 um, 19*150 mm,; mobile phase, water 0.03% NH3H2O and CH3CN (14% CH3CN up to 27% in 7 min, up to 100% in 2 min, down to 14% in 1 min); Detector, Waters 2489 254&220 nm to afford the title compound as a white solid. 1H-NMR(400 MHz, DMSO-d6) δ ppm 1.54-1.66(m, 2H), 1.75(m, 1H), 1.99(m, 1H), 2.61-2.73(m, 2H), 2.80-2.85(m, 1H), 3.14-3.16(m, 1H), 3.69(m, 8H), 4.15-4.16(m, 1H), 7.38(s, 1H), 7.75-7.77(m, 1H), 7.97-8.00(m, 1H), 8.08(s, 1H), 8.26(s, 1H), 10.77-10.79(d, J=7.6 Hz, 1H). MS m/z [M+H]+ (ESI): 456. IRAK4 IC50=10 nM

Provenance & Evidence