HCID 59850190, compound → HCID 59850141, compound

A solution of 5,6-difluoro-1-[1-(phenylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1,3-dihydro-2H-benzimidazol-2-one (D88) (0.7 mmol, 240 mg) in ethanol (10 mL) and acetic acid (2 mL) was treated under argon with 10% palladium on charcoal (50 mg, ˜0.25 eq wt) and the mixture was stirred overnight under 25-30 PSI, then 8 h under 50 PSI of hydrogen at room temperature. The mixture was concentrated under reduced pressure to give a yellow/orange oil which crystallized with a touch of methanol (from evaporation of the methanol). The residue was dissolved again in 10 mL ethanol and 2 mL of acetic acid, then 50 mg of palladium on charcoal was added again under argon and the mixture was stirred under 50 PSI of hydrogen for 9 days, until completion of the reaction. The mixture was concentrated under reduced pressure to give the title compound as the acetate salt. M+H 254.2, M−H 252.2

1. custom8 h
2. customat room temperature
3. concentrationThe mixture was concentrated under reduced pressure
4. customto give a yellow/orange oil which
5. customcrystallized with a touch of methanol (
6. customfrom evaporation of the methanol)
7. dissolutionThe residue was dissolved again in 10 mL ethanol
8. addition2 mL of acetic acid, then 50 mg of palladium on charcoal was added again under argon
9. stirringthe mixture was stirred under 50 PSI of hydrogen for 9 days, until completion of the reaction
10. concentrationThe mixture was concentrated under reduced pressure

ORD record

ord-6cdee230261b41f990742022139924e8

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288412B2