Hydrochloric Acid → HCID 16755509, compound

Participants

Reaction Conditions

Reaction Steps

To separate solutions of 5-(3-amino-2-(R)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-13) (0.60 g, 1.1 mmol, 1 equiv) and 5-(3-amino-2-(S)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-14) (0.70 g, 13 mmol, 1 equiv) in methanol (20 mL) was added 4 N HCl solution in dioxane (30 mL) and the resulting solutions were stirred at 40° C. for 16 h. The clear gel precipitate was filtered, and the filtered solid was washed with ethyl acetate, dissolved in water and concentrated to yield the hydrochloride salts of 5-(3-amino-2-(R)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-15) and 5-(3-amino-2-(S)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-16) as white solids. 1H NMR (500 MHz, CD3OD) δ 7.76 (s, 1H), 7.39 (s, 1H), 5.20 (m, 1H), 4.66 (m, 2H), 3.46 (m, 2H), 2.94 (m, 4H), 2.71 (s, 3H), 1.87 (m, 4H). LRMS m/z (M+H) 329.2 found, 329.2 required.

Provenance & Evidence