1-Butanol → 8-[5-(1-Hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one fumarate

Participants

Reaction Conditions

Reaction Steps

Example 5 can be prepared as by adding free base 8-[5-(1-hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (60.2 mg) to 1-butanol (0.5 mL) and then add 21.9 mg fumaric acid. Add heptane (5×0.5 mL), which produces thick white slurry, and stir at 90° C./500 rpm. Vacuum filter and dry under nitrogen. Solids are lost during recovery from filtration, though sufficient for XRD. Additional crystalline fumarate salt is prepared by adding free base (101.0 mg) to 1-butanol (0.5 mL) and then add 34 mg fumaric acid. Add heptane (6×0.5 mL) and crystalline seeds of the fumarate salt from first preparation and stir the mixture at 90° C./500 rpm for 1 hour. Recover the solids by vacuum filtration and dry the solids under nitrogen. Further dry the solids in a vacuum oven (65° C.) overnight to provide the title compound.

Provenance & Evidence