HCID 71253068, compound → HCID 54589064, compound

Participants

Reaction Steps

A solution of N-(4-(4-(3-(3-tert-butyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide (270 mg, 0.443 mmol) in a mixture of MeOH (20 mL) and AcOH (1.0 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, 40° C., 55 mm, 10% Pt—C Cat-Cart, full hydrogen mode). The reaction mixture was evaporated in vacuo and the residue was partitioned between EtOAc (15 mL) and saturated aq. NaHCO3 (15 mL). The organic layer was separated and was washed with brine (15 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 20-100%, gradient elution) to afford the title compound, Example 1, as a pale brown solid (115 mg, 43%); Rt 4.87 min (Method 1 basic); m/z 580 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) δ: 1.25 (9H, s), 3.30 (3H, s), 3.98 (2H, s), 5.41 (2H, s), 6.34 (1H, s), 6.68-6.71 (3H, overlapping m), 7.14 (2H, d), 7.33 (1H, d), 7.57 (1H, m), 7.63-7.67 (2H, overlapping m), 7.83 (1H, d), 7.98 (1H, dd), 8.09 (1H, d), 8.18 (1H, d), 8.65 (1H, s), 9.18 (1H, s), 10.04 (1H, s).

Provenance & Evidence