benzyl {1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}methylcarbamate → 1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methylethanamine

HRID 425393Notes

Reaction equation

HRID 425393 reaction equation
[CH3:1][C:2]([CH3:39])([CH2:37][CH3:38])[CH2:3][C:4]1[N:8]([CH3:9])[C:7]([CH:10]([N:25](C)[C:26](=O)OCC2C=CC=CC=2)[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)=[CH:14][CH:13]=2)=[N:6][CH:5]=1>CO.[Pd]>[CH3:1][C:2]([CH3:39])([CH2:37][CH3:38])[CH2:3][C:4]1[N:8]([CH3:9])[C:7]([CH:10]([NH:25][CH3:26])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)=[CH:14][CH:13]=2)=[N:6][CH:5]=1

Participants

4

Reactant 1

HCID 86637801benzyl {1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}methylcarbamate

Product 1

HCID 591404041-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methylethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd (10 wt % on activated carbon) (catalytic) was added to a degassed, ambient temperature solution of benzyl {1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}methylcarbamate (11 mg, 0.02 mmol) in methanol (3 mL). After stirring at ambient temperature under an atmosphere of hydrogen for 4 h, the reaction mixture was filtered through cotton and concentrated in vacuo to afford the title compound. (M+H) found: 395.

Workup

  1. filtrationthe reaction mixture was filtered through cotton
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a42055d204f64873827dc6d48b91d4e6
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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