Ethanol → HCID 178456445, compound

HRID 250764Notes

Reaction equation

HRID 250764 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([NH:25][CH:26]([CH3:28])[CH3:27])[CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Li+].[N:32]#[C:33]Br.C(O)C>ClCCl>[CH:26]([N:25]1[C:20]2[CH:19]=[C:18]([C:9]3[NH:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=3[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:23]=[CH:22][C:21]=2[N:24]=[C:33]1[NH2:32])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 10476Cyanogen BromideHCID 4177230Lithium methanolateHCID 178456733HCID 178456733, compound

Product 1

HCID 178456445HCID 178456445, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 2,4-diphenyl-5-(3-(isopropyl)amino-4-aminophenyl)imidazole (0.075 g, 0.20 mmol), lithium methoxide (0.41 mmol, 15 mg) and cyanogen bromide (0.6 mmol, 0.2 ml of 3N in dichloromethane) in dichloromethane (5 ml) under nitrogen for 1 hour. Add ethanol (5 ml), and continue stirring for 5 hours. Pour reaction mixture over an SCX column, and elute sequentially with methanol followed by 2N ammonia in methanol. Combine the basic fractions and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 9:1 dichloromethane:methanol to provide the title compound as a white solid (30 mg, 38%).

Workup

  1. additionPour
  2. customreaction mixture over an SCX column
  3. washelute sequentially with methanol
  4. concentrationconcentrate under reduced pressure
  5. washeluting with 9:1 dichloromethane

Sources & evidence

ORD record
ord-57382bbeca37415baadfce9514009021
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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