HCID 68810823, compound → HCID 9842488, compound

Participants

Reaction Steps

{1-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester G (8.40 g, 17.7 mmol) was dissolved in 50 mL of trifluoroacetic acid (TFA) under an atmosphere of dry N2. The reaction mixture was stirred at ambient temperature for 15 minutes after which time it was concentrated under vacuum to give a yellow oil. The oil was partitioned between DCM and 0.1N aqueous NaOH. The DCM layer was washed again with 0.1N aqueous NaOH. The DCM layer was dried over Na2SO4, filtered and concentrated to give 5.85 g of 1-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-ylamine as a yellow solid. C.I. m/z 374 [M+1]; 1H NMR (CDCl3) δ 8.66 (s, 1 H), 8.37 (d, J=8.9 Hz, 1 H), 8.30 (d, J=8.7 Hz, 1 H), 7.68 (d, J=8.9 Hz, 1 H), 7.47 (m, 2 H), 7.35 (d, J=2.3 Hz, 1 H), 7.25 (m, 1 H), 7.06 (dd, J=2.5, 8.9 Hz, 1 H), 3.91 (s, 3 H), 3.88 (m, 2 H), 2.90 (m, 3 H), 2.05 (m, 2 H), 1.83 (m, 2 H), 1.50 (brs, 2 H).

Provenance & Evidence