Aniline → HCID 89783279, compound

Participants

Reaction Steps

8-(4-Oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoline-2-carboxylic acid (Example 94e; 80 mg, 0.26 mmol) was dissolved in DMF (2.5 mL), HATU (119 mg, 0.31 mmol), Et3N (0.04 mL, 0.31 mmol), and aniline (0.05 mL, 0.52 mmol) were added, and the resulting mixture was stirred at RT for 20 min. The mixture was then treated with EtOAc and washed with water. The organic layer was separated, and the aq. layer was extracted with EtOAc (2×). The combined organic layers were then dried over MgSO4, filtered, and concentrated to in vacuo. DCM was added to the crude material and a precipitate was formed, which contained both the desired product and impurities. Most of the impurities crystallized from hot DCM, and were removed by filtration. The mother liquor was concentrated and the material (desired product and ca. 10% impurity) was suspended in EtOAc. The desired product was recrystallized from hot EtOAc and was isolated by filtration affording 8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-N-phenylquinoline-2-carboxamide (12.9 mg, 0.034 mmol, 13.0% yield) as an amorphous tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.04 (br. s., 1H), 10.55 (s, 1H), 8.68 (d, J=8.4 Hz, 1H), 8.25 (d, J=8.4 Hz, 1H), 8.11 (d, J=7.2 Hz, 1H), 7.99 (d, J=7.6 Hz, 1H), 7.93 (d, J=8.0 Hz, 2H), 7.72-7.81 (m, 1H), 7.44 (t, J=7.7 Hz, 2H), 7.13-7.22 (m, 1H), 7.07 (d, J=10.8 Hz, 2H), 3.44-3.53 (m, 2H), 2.95 (t, J=6.7 Hz, 2H). m/z (ESI, +ve ion) 383.0 (M+H)+.

Provenance & Evidence