Hydrogen Bromide → 1-Methyl-1-N-[5-(trifluoromethyl)pyrimidin-2-yl]cyclopentane-1,2-diamine

To a solution of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl N-(2-methyl-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl)carbamate (1.04 g, 2.35 mmol) in acetic acid (8 ml) was added HBr (1.28 ml, 23.48 mmol). The reaction was heated sealed and heated at 90° C. overnight. To this was then added further HBr (1.28 ml, 23.48 mmol) and the reaction mixture heated at 90° C. for 24 hours. Further acetic acid (5 ml) and HBr (5 ml) was added and the reaction mixture heated to 90° C. for 5 hours. The reaction mixture was concentrated in vacuo and azeotropically distilled with toluene. The resulting residue was purified by SCX chromatography (2M ammonia in methanol) to afford the title compound as a single trans-enantiomer.

1. temperatureThe reaction was heated
2. customsealed
3. temperaturethe reaction mixture heated at 90° C. for 24 hours
4. temperaturethe reaction mixture heated to 90° C. for 5 hours
5. concentrationThe reaction mixture was concentrated in vacuo
6. distillationazeotropically distilled with toluene
7. customThe resulting residue was purified by SCX chromatography (2M ammonia in methanol)

ORD-Eintrag

ord-6ee1f216dc6847c6a1502b16c0ba0b33

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09156829B2