Triethylamine → HCID 68328255, compound

Participants

Reaction Steps

To a solution of cyclopropanecarboxylic acid (55 mg, 0.642 mmol) in DMF (6 mL) was added EDC.HCl (167 mg, 0.875 mmol), HOBt (118 mg, 0.875 mmol) and triethylamine (0.244 mL, 1.75 mmol). The mixture was stirred for 15 min, then 5-(3-amino-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (150 mg, 0.583 mmol) was added and the mixture was stirred for 16 h at RT. The reaction was quenched with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with basic alumina chromatography to give N-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)cyclopropane carboxamide (21 mg, 11%). MS (ESI, pos. ion) m/z: 326.2 (M+1); 1H-NMR (300 MHz, DMSO-d6): δ 11.13 (s, 1H), 10.43 (s, 1H), 8.37 (brs, 1H), 7.75 (d, 1H, J=2.1 Hz), 7.41-7.55 (m, 3H), 3.70-3.76 (m, 1H), 1.92-1.97 (m, 1H), 1.21 (d, 6H, J=6.6 Hz), 0.77-0.79 (m, 4H).

Provenance & Evidence