Tetrahydrofuran → HCID 17751814, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium methoxide in MeOH (25% by wt, 211 mg, 0.98 mmol) was taken up in MeOH (2 mL) and THF (8 mL) and the solution cooled to 0° C. Toluenesulfonylmethylisocyanide (96.6 mg, 0.49 mmol) and N-[4-(4-amino-7-formylpyrrolo[2,1-f][1,2,4]triazin-5-yl)-2-fluorophenyl]-N′-[4-(trifluoromethyl)pyridin-2-yl]urea (150 mg, 0.33 mmol) were added in succession to the solution. The reaction was stirred at 0° C. for 5 min, then heated at 60° C. for 1 h. The reaction was cooled to rt and diluted with EtOAc (100 mL). The organic layer was wash with water (2×) and dried with sodium sulfate. The suspension was filtered and the filtrate concentrated in vacuo. The resulting solid was triturated with ether, and subsequently with THF to provide the title compound (67 mg, 41%) as a tan solid. 1H-NMR (DMSO-d6) δ 9.43 (s, 1H), 9.30 (s, 1H), 8.65 (dd, 1H), 8.31 (t, 1H), 8.17 (s, 1H), 7.52 (t, 1H), 7.37-7.46 (m, 2H), 7.26-7.32 (m, 1H), 7.23 (m, 1H); MS [M+H]+=499.1; LCMS RT=3.00 min.

Provenance & Evidence