Ethanol → (R)-1-(4-Fluorophenyl)-6-(6-morpholin-4-yl-pyridine-3-sulfonyl]-1,4,5,6,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene-4a-carboxylic acid ethyl ester

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Reaction Steps

A solution of (R)-1-(4-fluorophenyl)-6-(6-morpholin-4-yl-pyridine-3-sulfonyl]-1,4,5,6,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene-4a-carbonyl chloride (0.1 g) in dry dichloromethane (5 mL) was treated with absolute ethanol (0.2 g) and triethylamine (0.1 g) for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (1:4 to 2:3 by volume) to afford the title compound as a white solid (0.057 g). 1H NMR (400 MHz, CHCl3-d): δ 8.53 (d, 1H), 7.77 (dd, 1H), 7.48-7.36 (m, 3H), 7.19-7.11 (m, 2H), 6.61 (d, 1H), 6.40 (d, 1H), 4.37 (d, 1H), 4.17 (qd, 2H), 3.80 (t, 5H), 3.66 (t, 4H), 3.29 (d, 1H), 2.95-2.86 (m, 1H), 2.57 (d, 1H), 2.44-2.34 (m, 3H), 1.25 (t, 3H).

Provenance & Evidence