Cyanogen Bromide → HCID 66868777, compound

HRID 250770Notes

Reaction equation

HRID 250770 reaction equation
[N:1]#[C:2]Br.[CH2:4]([NH:8][C:9]1[CH:10]=[C:11]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[CH:13][C:14]=1[NH2:15])[CH:5]([CH3:7])[CH3:6]>C(O)(C)C.C(OCC)(=O)C>[CH2:4]([N:8]1[C:9]2[CH:10]=[C:11]([N:16]3[CH:20]=[CH:19][N:18]=[C:17]3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=[CH:13][C:14]=2[N:15]=[C:2]1[NH2:1])[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 66868538HCID 66868538, compound

Product 1

HCID 66868777HCID 66868777, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add cyanogen bromide (177 mg, 1.67 mmol) to a solution of 1-(3-(isobutylamino)-4-aminophenyl)-2-phenyl-1H-imidazole (410 mg, 1.34 mmol) in 10 mL isopropanol cooled to 0° C. Stir for one hour at this temperature and then stir at room temperature over night. Dilute with ethyl acetate and wash with 1N sodium hydroxide. Dry the organic layer over sodium sulfate, filter, and concentrate under reduced pressure. Subject the residue to radial silica gel chromatography, eluting with methanol containing 4% methanol to provide the title compound as a tan solid (220 mg, 50%).

Workup

  1. stirringstir at room temperature over night
  2. washwash with 1N sodium hydroxide
  3. dry with materialDry the organic layer over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. washeluting with methanol containing 4% methanol

Sources & evidence

ORD record
ord-d7bafc3a450d44319be8bf9ddf462dd5
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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