Trifluoroacetic acid → HCID 9841718, compound

Participants

Reaction Steps

Trifluoroacetic acid (3 ml) was added to a solution of 3-phenyl-5-(pyridin-2-ylmethoxy)-8,9-dihydro-6H-1,2,3a,4,7-pentaazacyclopenta[α]-naphthalene-7-carboxylic acid tert-butyl ester (217 mg, 0.47 mmol) in dry dichloromethane (3 ml) at 0° C. under nitrogen. After 1 hour the volatiles were removed in vacuo and the residue was partitioned between dichloromethane and saturated aqueous potassium carbonate. The aqueous was further extracted with dichloromethane (×2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol/ammonia (60:8:1) to afford the title amine (162 mg, 96%) as a colourless solid, m.p.=157-159° C. 1H NMR (360 MHz, d6-DMSO) δ2.92-2.96 (2H, m), 3.07 (2H, t, J=5.8 Hz), 3.84 (2H, s), 5.56 (2H, s), 7.36 (1H, dd, J=6.7, 4.9 Hz), 7.52-7.60 (4H, m), 7.87 (1H, td, J=7.8, 1.7), 8.23 (2H, dd, J=6.3, 1.9 Hz), 8.62-8.64 (1H, m). MS (ES+) m/e 359 [MH]+. Anal. Found C, 64.93; H, 5.31; N, 22.30. C20H18N6O.0.75 H2O requires C, 64.59; H, 5.29; N, 22.60%.

Provenance & Evidence