Ammonia → HCID 54589267, compound

Participants

Reaction Steps

To a solution of 1-(4-(2-aminopyridin-4-ylthio)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea (44 mg, 0.084 mmol) and DIPEA (52 μL, 0.30 mmol) in DCM (2.0 mL) was added a solution of 2-methoxyacetyl chloride (19 μL, 0.21 mmol) in DCM (0.5 mL) over 5 min. The reaction mixture was kept at RT for 30 min and a solution of NH3 (1% in MeOH, 1.0 mL) was added. The mixture was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, 12 g, EtOAc in isohexane, 30-80%, gradient elution) to afford the title compound, Example 21, as a white solid (36 mg, 70%). Rt 2.76 min (Method 2); m/z 595 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) δ: 1.28 (9H, s), 2.39 (3H, s), 3.28 (3H, s), 3.95 (2H, s), 6.44 (1H, s), 6.56 (1H, dd), 7.37 (2H, d), 7.47 (2H, d), 7.65 (2H, m), 7.75 (1H, s), 7.93 (1H, d), 8.02 (1H, d), 8.17-8.23 (3H, overlapping m), 8.97 (1H, s), 9.37 (1H, s), 9.90 (1H, s).

Provenance & Evidence