Potassium Carbonate → (Cis)-2-[(5-bromopyridin-3-yl)amino]-N-(2,2,2-trifluoroethyl)cyclohexane carboxamide

Temperature

80 °C

To a nitrogen degassed mixture of 3,5-dibromopyridine (8.5 g, 35.9 mmol), (cis)-2-amino-N-(2,2,2-trifluoroethyl)cyclohexanecarboxamide hydrochloride, I-5b, (9.35 g, 35.9 mmol), potassium carbonate (19.84 g, 144 mmol) and L-proline (0.826 g, 7.18 mmol), in DMSO (70 ml) was added copper(i) iodide (Strem® crushed) (0.683 g, 3.59 mmol). The reaction was sealed and heated at 80° C. for 64 hrs. Reaction was quenched into water (500 mL) and resulting solid product filtered and then slurry washed with water (50 mL). The wet solid was dissolved in ethyl acetate (400 mL), dried over sodium sulfate, filtered thru pad of silica to remove baseline material and filtrate concentrated to give 7.4 gm tan solid. Solid slurried in ˜50 mL diethyl ether for 15 min, filtered washed with hexane and solid sucked dry under nitrogen to give 5.73 gm product, I-5. LRMS (ESI) m/z 380.1 [(M+H)+; calcd for C14H17BrF3N3O: 380.1].

1. customTo a nitrogen degassed
2. customThe reaction was sealed
3. customReaction
4. customwas quenched into water (500 mL)
5. customresulting solid product
6. filtrationfiltered
7. washslurry washed with water (50 mL)
8. dissolutionThe wet solid was dissolved in ethyl acetate (400 mL)
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customto remove baseline material and filtrate
12. concentrationconcentrated

ORD record

ord-96cd8c0334514c69b459ebef093b7194

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096598B2