Hydrochloric Acid → HCID 136983868, compound

Participants

Reaction Steps

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[5-(5-bromo-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (60.0 mg, 0.10 mmol, 1.00 equiv) and cone, hydrochloric acid (4.0 mL). The crude product (100 mg) was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001 (SHIMADZU)): Column, SunFire Prep C18 OBD Column, 5 um, 19*150 mm,; mobile phase, water with 50 mmol NH4HCO3 and CH3CN (38.0% CH3CN up to 53.0% in 7 min, up to 100.0% in 5 min, down to 38.0% 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 1.54-1.72(m, 3H), 1.92-1.93(m, 1H), 2.65-2.75(m, 2H), 2.86(m, 1H), 3.10-3.13(m, 1H), 3.62-3.69(m, 8H), 4.17(m, 1H), 7.37-7.39(d, J=8.4 Hz, 1H), 7.89-7.94(m, 2H), 10.74-10.75(m, 1H); MS m/z [M+H]+ (ESI): 492. IRAK4 IC50=19 nM

Provenance & Evidence