Hydrochloric Acid → HCID 67951256, compound

To a round bottomed flask was added 6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepine-4-carbonitrile (32 mg, 0.096 mmol) and conc. HCl (1 mL, 32.9 mmol). The reaction was stirred at room temperature for 1 h and during this time a precipitate formed. This solution was diluted with water and the precipitate was collected via filtration. Upon washing with water the precipitate dissolved. The layers were separated and the aqueous was extracted with ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. This crude mixture was taken up in DCE (1 mL) and TFA (1 mL, 12.98 mmol). The vial was sealed and the reaction heated to 80° C. for 1 h before cooling to room temperature and stirring for an additional 2 h. The solution was concentrated and the crude residue was purified via Biotage (EtOAc/hex) to afford the titled compound (16.2 mg, 0.046 mmol) as a white solid. LC/MS m/z 352 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.07-7.86 (m, 2H), 7.82 (d, J=7.8 Hz, 1H), 7.71 (t, J=7.2 Hz, 1H), 7.52-7.47 (m, 2H), 7.46-7.36 (m, 4H), 4.73-4.42 (m, 1H), 2.50 (s, 3H)

1. customformed
2. filtrationthe precipitate was collected via filtration
3. washUpon washing with water the precipitate
4. dissolutiondissolved
5. customThe layers were separated
6. extractionthe aqueous was extracted with ether (3×)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe vial was sealed
12. temperaturethe reaction heated to 80° C. for 1 h
13. temperaturebefore cooling to room temperature
14. stirringstirring for an additional 2 h
15. concentrationThe solution was concentrated
16. customthe crude residue was purified via Biotage (EtOAc/hex)

ORD record

ord-68677f65dede4d6b91bbcfd0d1f1a2a6

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796261B2