Dimethylformamide → HCID 11562615, compound

Participants

Reaction Steps

A mixture of 5-(2-(tert-butoxycarbonyl)ethylamino)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (50 mg, 0.13 mmol) and 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (40 mg, 0.16 mmol, Compound B of Example 132), BOP reagent (100 mg, 0.23 mmol) in DMF (1 mL) was stirred at 50° C. with triethylamine (0.1 mL) for 1 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with methylene chloride (3×10 mL). The combined organic extracts were washed with water, dried and concentrated in vacuo. The residue was stirred with TFA (1 mL) at room temperature for 30 minutes. The TFA was removed and the residue was purified by preparative HPLC. The fraction containing the desired product was collected and concentrated in vacuo. The residue was converted to the HCl salt by adding 1 N HCl solution and lyophilizing to give the title compound (20 mg, 27%). 1H NMR (CD3OD) δ 8.35 (d, 1H, J=2.6 Hz), 8.26 (d, 1H, J=5.5 Hz), 8.01 (dd, 1H, J=10.4, 2.6 Hz), 7.48 (m, 2H), 7.41 (m, 6H), 6.81 (d, 1H, J=5.5 Hz), 6.60 (s, 1H), 3.26 (t, 2H, J=6.1 Hz), 3.07 (t, 2H, J=6.1 Hz); MS(ESI+) m/z 517 (M+H)+.

Provenance & Evidence