Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 1,4-Cyclohexadiene | HCID 12343 | — |
| Reactant | 1-Benzyl-2-methyl-4-(3-(N-[3-methylbut-2-yl]-N-[cyano]amino)-4-nitrophenyl)-5-(2,4-difluorophenyl)-1H-imidazole | HCID 86623268 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Product | HCID 178432527 | HCID 178432527 | — |
Reaction Steps
Combine 1-benzyl-2-methyl-4-(3-(N-[3-methylbut-2-yl]-N-[cyano]amino)-4-nitrophenyl)-5-(2,4-difluorophenyl)-1H-imidazole-(0.122 g, 0.24 mmol), 10% palladium on carbon (90 mg), and 1,4-cyclohexadiene (2 mL) in absolute ethanol (10 mL) and heat to 95° C. in a sealed vessel for 18 hours. Cool to room temperature, filter through celite, and concentrate the filtrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with dichloromethane/methano/ammonia mixtures to give 0.077 g (0.195 mmol) of 1-(3-methylbut-2-yl)-2-amino-6-(2-methyl-4-(2,4-difluorophenyl)-1H-imidazol-5-yl)-1H-benzimidazole. Dissolve in 10% methanol/dichloromethane, add 1.0 equivalent methanesulfonic acid, remove solvent under a stream of nitrogen and finally under high vacuum to give 0.094 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07863310B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-5198676acf574f98847c952f8a19fee8 |
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| Source note | uspto-grants-2011_01 |
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