Hydrochloric Acid → HCID 70976636, compound

Participants

Reaction Steps

A suspension of crushed tert-butyl ((2S,4R)-1-acetyl-6-(4-((2-(dimethylamino)ethyl)carbamoyl)phenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate (for a preparation see Intermediate 41) (8 g, possibly as the PF6 salt) was treated with 1,4-dioxane (30 mL) followed by hydrogen chloride in 1,4-dioxane (4N, 40 mL, 160 mmol). After −30 min most of the dioxane was removed and the residue dissolved in warm MeOH (100 mL) at 70° C. for 1.5 h. The residual insoluble material which was filtered off and discarded. The filtrate was concentrated in vacuo and purified using a SCX column (70 G, pre-conditioned with MeOH.) The cartridge was washed with MeOH (200 ml) and eluted with ammonia in MeOH (2M, 200 ml). The methanolic ammonia fractions were combined and concentrated in vacuo to give 4-((2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-(dimethylamino)ethyl)benzamide (3.65 g, 9.25 mmol, 84% yield) as a yellow foam. LCMS (HpH, 2 min), Rt=0.71 min, MH+=395.

Provenance & Evidence