Cyanogen Bromide → HCID 66869562, compound

HRID 250766Notes

Reaction equation

HRID 250766 reaction equation
[N:1]#[C:2]Br.[CH:4]1([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:16]=3)=[C:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:12]=[CH:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>C(O)C>[CH2:23]([N:22]1[C:17]2[CH:16]=[C:15]([C:14]3[N:10]([CH:4]4[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]4)[CH:11]=[N:12][C:13]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:20]=[CH:19][C:18]=2[N:21]=[C:2]1[NH2:1])[CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 66868837HCID 66868837, compound

Product 1

HCID 66869562HCID 66869562, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add cyanogen bromide (101 mg, 0.96 mmol) to a solution of 1-(cyclohexyl)-4-phenyl-5-(3-(isobutylamino)-4-aminophenyl)-1H-imidazole (250 mg, 0.64 mmol) in 6 mL ethanol. Stir over night at room temperature. Add saturated aqueous sodium carbonate and extract well with 9:1 ethyl acetate:methanol. Combine the organic phases, dry over magnesium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with a gradient of 5-8% methanol in dichloromethane to provide the title compound (52%).

Workup

  1. extractionAdd saturated aqueous sodium carbonate and extract well with 9:1 ethyl acetate
  2. dry with materialdry over magnesium sulfate
  3. concentrationconcentrate under reduced pressure
  4. washeluting with a gradient of 5-8% methanol in dichloromethane

Sources & evidence

ORD record
ord-c9f809c6aad942f19aa9d0b07504c6a8
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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