Diisopropylethylamine → HCID 59451616, compound

Participants

Reaction Steps

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (25.0 mg, 0.080 mmol), 5-({2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}oxy)-1H-indole-2-carboxylic acid (24.53 mg, 0.080 mmol) and DIPEA (0.014 mL, 0.080 mmol) in DMF (1 mL) was added HATU (30.6 mg, 0.080 mmol). After 2 h the reaction mixture was poured into EtOAc and water. The organic layer was separated, dried over MgSO4 and the solvent evaporated. The residue 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 (0.019 g, 42%) as a white solid. 1H NMR (400 MHz, Acetone-d6): δ ppm 10.67 (br. s., 1H), 8.31 (t, 1H), 7.60 (t, 1H), 7.46 (d, 1H), 7.40-7.42 (m, 1H), 7.38-7.40 (m, 1H), 7.34-7.38 (m, 2H), 7.07 (d, 1H), 7.04 (d, 1H), 6.88 (dd, 1H), 4.67 (d, 2H), 4.04-4.17 (m, 2H), 3.82-3.91 (m, 1H), 3.51-3.58 (m, 1H), 3.43-3.50 (m, 1H), 1.92-2.01 (m, 1H), 1.73-1.84 (m, 1H). LCMS m/z 558.0 (M+1).

Provenance & Evidence