Potassium Hydroxide → HCID 178424013, compound

Participants

Reaction Conditions

Reaction Steps

(±)-2-(5-Hydroxy-6,8-dimethyl-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)-1H-benzo[d]imidazole-5-carbonitrile (41 mg, 0.083 mmol) in EtOH (0.83 mL) was treated with isomylamine (190 μL, 1.65 mmol) and KOH (46.3 mg, 0.826 mmol) and heated in a microwave for 30 minutes at 100° C. After 30 minutes an additional aliquot of isomylamine (190 μL, 1.65 mmol) and KOH (46.3 mg, 0.826 mmol) were added and the reaction heated in a microwave. After 30 minutes the reaction was complete. It was directly loaded onto a column and purified using FCC eluting with heptane:EtOAc 1:2 to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.79 (s, 1H), 10.59 (br. s., 1H), 7.89-7.95 (m, 1H), 7.55-7.72 (m, 1H), 7.34-7.55 (m, 1H), 7.01 (s, 1H), 6.56 (s, 1H), 6.15 (m, 1H), 2.89-2.90 (m, 2H), 2.27-2.45 (m, 5H). HRMS calcd. for C21H18N4O (M+H)+ 343.1554. found 343.156.

Provenance & Evidence