To a stirred solution of 1-{4-[(2-aminopyridin-4-yl)methoxy]naphthalen-1-yl}-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea (5) (526 mg, 0.96 mmol) and DIPEA (184 μL, 1.06 mmol) in mixture of DCM and DMF (10:1, 11 mL) was added methoxyacetyl chloride (92 μL, 1.01 mmol). After 1 h at RT further aliquots, of DIPEA (184 μL, 1.06 mmol) and methoxyacetyl chloride (92 μL, 1.01 mmol) were added sequentially and stirring was continued for 1 h. A solution of 1% ammonia in MeOH (40 mL), was added and the mixture stirred for 15 mins and then concentrated in vacuo. The crude product was purified by flash column chromatography (Biotage 40 g); eluting with 0 to 6% MeOH in DCM to furnish N-[4-({4-[3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido]naphthalen-1-yloxy}methyl)pyridin-2-yl]-2-methoxyacetamide (1) (286 mg, 49%): m/z 593 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 1.27 (9H, s), 2.39 (3H, s), 3.32 (3H, s), 4.08 (2H, s), 5.39 (2H, s), 6.36 (1H, s), 7.03 (1H, d), 7.28 (1H, dd), 7.36 (2H, m), 7.44 (2H, m), 7.56-7.64 (3H, m), 7.93 (1H, m), 8.30-8.35 (3H, m), 8.58 (1H, s), 8.79 (1H, s) and 10.02 (1H, s).
