Ethanol → HCID 178432527, compound

HRID 250771Notes

Reaction equation

HRID 250771 reaction equation
C([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])=[C:11]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([N:30]([CH:33]([CH:35](C)C)C)[C:31]#[N:32])[CH:22]=2)[N:10]=[C:9]1[CH3:38])C1C=CC=CC=1.[CH:39]1CC=CCC=1.[CH2:45](O)[CH3:46]>[Pd]>[CH3:39][CH:45]([CH3:46])[CH:33]([N:30]1[C:23]2[CH:22]=[C:21]([C:11]3[NH:10][C:9]([CH3:38])=[N:8][C:12]=3[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[F:20])[CH:26]=[CH:25][C:24]=2[N:27]=[C:31]1[NH2:32])[CH3:35]

Participants

5

Reactant 3

HCID 702EthanolHCID 123431,4-CyclohexadieneHCID 866232681-Benzyl-2-methyl-4-(3-(N-[3-methylbut-2-yl]-N-[cyano]amino)-4-nitrophenyl)-5-(2,4-difluorophenyl)-1H-imidazole

Product 1

HCID 178432527HCID 178432527, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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.

Workup

  1. filtrationfilter through celite
  2. concentrationconcentrate the filtrate under reduced pressure
  3. washeluting with dichloromethane/

Sources & evidence

ORD record
ord-5198676acf574f98847c952f8a19fee8
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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