Hydrochloric Acid → (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 3-hydroxycyclobutylmethyl ester

Participants

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-carboxylic acid 3-(tetrahydropyran-2yloxy)-cyclobutylmethyl ester in tetrahydrofuran (0.6 mL) was treated with 4.0 M hydrogen chloride in dioxan (1.0 mL) for 30 minutes. The reaction mixture was evaporated under reduced pressure, the residue dissolved in dichloromethane and the solution washed with 2.0M sodium carbonate solution and brine. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC eluting with a mixture of acetonitrile and water containing 0.1% formic acid (2:3 to 85:15 by volume) to give the title compound as a white solid (0.007 g). 1H NMR (400 MHz, CHCl3-d): δ 8.52 (d, 1H), 7.77 (dd, 1H), 7.40-7.30 (m, 3H), 7.18-7.10 (m, 2H), 6.62 (d, 1H), 6.42 (d, 1H), 4.38-4.30 (m, 2H), 4.11 (dd, 2H), 3.80 (t, 5H), 3.66 (t, 4H), 3.27 (d, 1H), 2.88-2.80 (m, 1H), 2.58 (d, 1H), 2.48-2.34 (m, 4H), 2.18-2.06 (m, 4H).

Provenance & Evidence