Potassium Carbonate → HCID 178418831, compound

Participants

Reaction Steps

To a solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (397 mg, 1.0 mmol) in THF (10 mL) was added N,N′-di-t-butoxycarbonyl-pyrazole-1-carboxamidine (370 mg, 1.2 mmol) and potassium carbonate (207 mg, 1.5 mmol) and the mixture stirred at room temperature for 16 h. The reaction was diluted with aqueous NH4Cl (15 mL) and the mixture extracted with ethyl acetate (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered, concentrated and purified by chromatography on silica gel (19:1 CH2Cl2/MeOH) to afford N′,N″-di-t-butoxycarbonyl-N-(4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-methyl}-benzyl)-guanidine as a pale foam (426 mg, 67%). 1H NMR (CDCl3) δ 1.25 (s, 9H), 1.44 (s, 9H), 1.65 (m, 1H), 1.99 (m, 2H), 2.04 (m, 1H), 2.72-2.79 (m, 2H), 3.73 (s, 2H), 3.94 (d, 1H, J=16.1 Hz), 4.07 (m, 1H), 4.11 (d, 1H, J=16.1 Hz), 4.51 (d, 2H, J=6.2 Hz), 7.14 (m, 4H), 7.39 (m, 3H), 7.55 (m, 1H), 7.63 (m, 1H), 8.47 (m, 1H (NH)), 8.66 (d, 1H, J=4.8 Hz).

Provenance & Evidence