Ethanol → 1-(4-oxo-3,4,6,7,8,9-hexahydro-benzo[g]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid

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Reaktionsschritte

Preparation of 1-(4-oxo-3,4,6,7,8,9-hexahydro-benzo[g]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester. HCl (4M in dioxane, 2.1 mL, 8.3 mmol) was added to a solution of 1-[3-(2-methoxy-ethoxymethyl)-4-oxo-3,4,6,7,8,9-hexahydro-benzo[g]quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.254 g, 0.596 mmol) and ethanol (2.0 mL). The reaction mixture was stirred at room temperature for 4 h, at which point ether (2 mL) was added and the precipitate was collected. The precipitate was triturated three times with ethanol, once with ethanol/THF (1:1), and once with DMSO. The filter cake was rinsed with ethanol and dried to yield the titled compound (89.4 mg, 44% yield). MS (ESI/Cl): mass calcd. for C18H18N4O3, 338.1; m/z found, 339.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 12.66 (s, 1H), 8.98 (s, 1H), 8.30 (s, 1H), 7.84 (s, 1H), 7.40 (s, 1H), 4.30 (q, J=7.1 Hz, 2H), 2.95-2.83 (m, 4H), 1.82-1.74 (m, 4H), 1.32 (t, J=7.1 Hz, 3H).

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