p-(Methylsulphonyl)benzoic acid → HCID 59451473, compound

Participants

Reaction Steps

In a 1 dram vial, 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (25 mg, 0.080 mmol), DIPEA (0.014 mL, 0.080 mmol) and 4-(methylsulfonyl)benzoic acid (16.09 mg, 0.080 mmol) were dissolved in DMF (1 mL). HATU was added (30.6 mg, 0.080 mmol) and the solution stirred overnight. The reaction mixture was diluted to 2 mL with MeOH. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.016 g, 39%) as a white solid. 1H NMR (400 MHz, Acetone-d6): δ ppm 8.59 (t, 1H), 8.11-8.18 (m, 2H), 8.00-8.07 (m, 2H), 7.63 (t, 1H), 7.47-7.53 (m, 1H), 7.41-7.45 (m, 1H), 7.36-7.41 (m, 2H), 4.70 (d, 2H), 3.16 (s, 3H). LCMS m/z 494.9 (M+1).

Provenance & Evidence