Aniline → HCID 58674485, compound

Participants

Reaction Steps

A mixture of 3-(4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenyl)-propanoic acid (100 mg, 0.33 mmol), aniline (0.033 mL, 0.36 mmol), and TBTU (117 mg, 0.36 mmol) in DCM (5 mL) was stirred at rt. To this slurry was added DIPEA (0.20 mL, 1.16 mmol). The mixture was allowed to stir at rt overnight and then diluted with water. The aqueous phase was separated and extracted with DCM. The organic solutions were combined, washed with brine, dried over MgSO4, filtered, and concentrated. The resulting solid was treated with MeOH and filtered to give 45 mg of a white solid. 1H NMR (400 MHz, d6-DMSO) δ: 9.90 (br s, 1H), 8.71-8.78 (m, 1H), 8.48 (d, J=5.6 Hz, 1H), 7.55-7.60 (m, 2H), 7.36-7.40 (m, 2H), 7.36 (d, J=2.4 Hz, 1H), 7.25-7.31 (m, 2H), 7.12-7.16 (m, 2H), 7.11 (dd, J=5.2, 2.4 Hz, 1H), 6.99-7.04 (m, 1H), 2.93-2.98 (m, 2H), 2.77 (d, J=4.8 Hz, 3H), and 2.64-2.69 (m, 2H).

Provenance & Evidence