Diisopropylethylamine → HCID 59451614, compound

Participants

Reaction Steps

HATU (0.055 g, 0.145 mmol) was added as a solid to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.045 g, 0.145 mmol), 5-{[2-(methylthio)ethyl]oxy}-1H-indole-2-carboxylic acid (0.036 g, 0.145 mmol) and DIPEA (0.025 mL, 0.145 mmol) in DMF (1 mL). After 2 hours the reaction mixture was poured into EtOAc and water and the layers were separated. The organic layer was dried over MgSO4, filtered and the solvent evaporated. The residue was dissolved in MeOH and purification was accomplished by reverse-phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.041 g, 52%) as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.64 (br. s., 1H), 8.28 (br. s., 1H), 7.61 (s, 1H), 7.33-7.51 (m, 5H), 7.00-7.13 (m, 2H), 6.89 (dd, 1H), 4.66 (d, 2 H), 4.15 (t, 2H), 2.85 (t, 2H), 2.17 (s, 3H). LC-MS (ES+) m/z 544.4 [M+H].

Provenance & Evidence