Hydrochloric Acid → HCID 178470362, compound

Participants

Reaction Steps

A solution of 300 mg of 6-tert-butyloxy-9-[5-(5,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-2,4,5,7,8,9-hexahydro-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester in 10 ml of dioxane is combined with 1.8 ml of 4N HCl in dioxane and the reaction mixture is stirred for 16 hours at room temperature. The formed insoluble material is collected by filtration, washed with dioxane (70 ml), pentane (50 ml), diisopropylether (50 ml) and dried under vacuum to yield 227 mg of 9-[5-(5,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester hydrochloride as a light brown powder. Yield=84%. Analytical LC/MS (method C): m/z=511 (negative ion mode [M−H]−), m/z=512 (positive ion mode [M+H]+) 500 MHz 1H NMR on a BRUKER AVANCE DRX-500 spectrometer, chemical shifts (δ in ppm) in d6 dimethylsufoxyde (DMSO-d6) solvent referenced at 2.50 ppm at 303K temperature: 1.28 (t, J=7.0 Hz, 3H); 3.72 (d broad, J=16.0 Hz, 1H); 3.81 (m, 1H); 4.22 (m, 1H); 4.28 (q, J=7.0 Hz, 2H); 4.45 (d broad, J=16.0 Hz, 1H); 5.20 (s, 1H); 6.40 (d, J=3.5 Hz, 1H); 6.85 (d, J=3.5 Hz, 1H); 6.90 (d, J=3.5 Hz, 1H); 7.06 (dt, J=2.0 et 11.0 Hz, 1H); 7.17 (dd, J=2.0 et8.5 Hz, 1H); 9.39 (s, 1H); 10.1 (m broad, 1H); 10.4 (m broad, 1H); 11.65 (d, J=3.5 Hz, 1H).

Provenance & Evidence