4-Methylmorpholine → HCID 45484114, compound

Temperature

-50 °C

To the solution of 2-biphenyl-4-yl-1H-benzoimidazole-4-carboxylic acid (0.35 g, 1.1 mmol) in THF (20 mL) was added N-methyl morpholine (0.2 mL, 1.6 mmol) and the mixture was cooled to −50° C. Isobutyl chloroformate (0.22 mL, 1.6 mmol) was then added drop wise, the reaction mixture was warmed to −10° C. and stirred for 2 h. The reaction mixture was again cooled to −50° C. and purged with ammonia gas for 10 minutes. Reaction mixture warmed to room temperature and stirred for 1 hour. TLC showed completion of the reaction. The crude mixture was filtered and the filtrate concentrated. The resulting residue was stirred with hexane and the free solid formed filtered and dried to obtain title compound (0.24 g, 70%).

1. temperaturethe reaction mixture was warmed to −10° C.
2. temperatureThe reaction mixture was again cooled to −50° C.
3. custompurged with ammonia gas for 10 minutes
4. customReaction mixture
5. temperaturewarmed to room temperature
6. stirringstirred for 1 hour
7. customcompletion of the reaction
8. filtrationThe crude mixture was filtered
9. concentrationthe filtrate concentrated
10. stirringThe resulting residue was stirred with hexane
11. customthe free solid formed
12. filtrationfiltered
13. customdried

ORD record

ord-13aa85332b56458fb3e61b5f5efcaf36

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006454B2