Sodium cyanoborohydride → 2-[3-(2-tert-Butoxycarbonylmethoxy-3,5-dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one

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Reaction Steps

To a solution of the compound prepared as in Example 1b (0.13 g, 0.45 mmol) in methanol (1 ml) and acetic acid (0.2 ml) was added sodium methoxide (0.5 M in methanol, 1.8 ml, 0.9 mmol). An aliquot of this solution (1.34 ml; 0.2 mmol 2-(3-aminoprop-1-ylamino)-1H-quinolin-4-one) was added to 2-tert-butoxycarbonylmethoxy-3,5-dichlorobenzaldehyde (0.061 g, 0.2 mmol) followed by sodium cyanoborohydride (0.02 g, 0.32 mmol) in methanol (0.6 ml). The mixture was stirred at room temperature under argon for 1 h. The product was purified by chromatography on a SCX cartridge, eluting with methanol and then 0.2M NH3 in methanol to give the title compound as a colourless gum (0.08 g, 79%); δH (CD3OD) 1.39 (9H, s), 1.8 (2H, m), 2.62 (2H, t), 3.33 (2H, t), 3.82 (2H, s), 4.52 (2H, s), 5.57 (1H, s), 7.1-7.5 (5H, m), and 7.99 (1H, dd): MS (ES+) 506, 508, 510 (12, 10, 3%, MH+), 450, 452 (10, 8%) and 201 (80).

Provenance & Evidence