Triethylamine → HCID 89783970, 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; 77 mg, 0.25 mmol) was dissolved in DMF (1.5 mL), HATU (114 mg, 0.30 mmol), Et3N (0.04 mL, 0.30 mmol), and 4-aminotetrahydropyran (Combi-Blocks Inc., San Diego, Calif.; 0.05 mL, 0.50 mmol) were added, and the resulting mixture was stirred at RT for 25 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. The residue was treated with DCM, and a precipitate formed. The DCM was heated, but the precipitate did not dissolve. The suspension was held at RT for 1 h, after which the solid was removed by filtration to give 8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)quinoline-2-carboxamide (31.2 mg, 0.08 mmol, 32% yield) as a bright yellow amorphous solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.00 (br. s., 1H), 8.55-8.67 (m, 2H), 8.08-8.16 (m, 2H), 7.93 (d, J=7.8 Hz, 1H), 7.68-7.77 (m, 1H), 6.94-7.05 (m, 2H), 4.00-4.15 (m, 1H), 3.90 (d, J=11.7 Hz, 2H), 3.42-3.52 (m, 4H), 2.91 (t, J=6.7 Hz, 2H), 1.92 (d, J=12.1 Hz, 2H), 1.59-1.74 (m, 2H). m/z (ESI, +ve ion) 391.1 (M+H)+.

Provenance & Evidence