Isoamylamine → HCID 178424035, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-2-(1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)-2-hydroxyethyl)-1H-benzo[d]imidazole-5-carbonitrile, isoamylamine (103 mg, 1.18 mmol) and KOH (66.0 mg, 1.18 mmol) in EtOH (2 mL) was stirred at 100° C. for 30 min under microwave irradiation. The reaction mixture was concentrated and the residue was partitioned between EtOAc and sat. aq. NH4Cl. The aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried over sodium sulfate and concentrated. The residue was purified with reverse phase HPLC (HC-B) to provide the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) 9.18 (br. s., 1H) 7.87 (br. s., 1H) 7.47 (d, J=7.07 Hz, 2H) 7.01 (t, J=2.84 Hz, 1H) 6.85 (s, 1H) 5.79-5.86 (m, 1H) 4.92 (dd, J=8.91, 5.49 Hz, 1H) 4.59 (dd, J=10.99, 9.09 Hz, 1H) 3.92 (dd, J=11.05, 5.49 Hz, 1H) 2.42 (s, 6H). MS (ESI+) m/z 331.3 (M+H).

Provenance & Evidence