Dimethyl Sulfoxide → HCID 44223787, compound

HRID 1877446Notes

Reaction equation

HRID 1877446 reaction equation
OO.[NH2:3][C:4]1[CH:11]=[C:10]([N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([C:25]4[NH:29][C:28]5[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:27]=5[N:26]=4)[C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].CS(C)=[O:37].[OH-].[Na+]>C(O)C.O>[NH2:3][C:4]1[CH:11]=[C:10]([N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([C:25]4[NH:29][C:28]5[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:27]=5[N:26]=4)[C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:9]=[CH:8][C:5]=1[C:6]([NH2:7])=[O:37]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67308411HCID 67308411, compound

Product 1

HCID 44223787HCID 44223787, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 50 ml round-bottomed flask, 0.2 ml of 30% aqueous hydrogen peroxide is added to a mixture of 40 mg of 2-amino-4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]benzonitrile, obtained in the preceding stage, in 1.0 ml of ethanol and 0.4 ml of dimethyl sulphoxide and 0.2 ml of 1M sodium hydroxide, and the mixture is stirred for ¼ hour at ambient temperature. 20 ml of distilled water are added and the mixture is extracted with 3 times 30 ml of ethyl acetate. The combined organic phases are washed with 30 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and evaporated to dryness under vacuum. The residue is chromatographed on silica gel (15-40 μm), elution being carried out with a mixture of dichloromethane and methanol (95/5 by volume). 24 mg of 2-amino-4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]benzamide are obtained in the form of a beige solid, the characteristics of which are the following:

Workup

  1. extractionthe mixture is extracted with 3 times 30 ml of ethyl acetate
  2. washThe combined organic phases are washed with 30 ml of a saturated solution of sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness under vacuum
  5. customThe residue is chromatographed on silica gel (15-40 μm), elution
  6. additionbeing carried out with a mixture of dichloromethane and methanol (95/5 by volume)

Sources & evidence

ORD record
ord-1129ed44ac3844a4bf0dda619f094047
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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