Hydrogen Peroxide → HCID 58338244, compound

HRID 1877463Notes

Reaction equation

HRID 1877463 reaction equation
F[C:2]1[CH:9]=[C:8]([N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([C:23]4[NH:27][C:26]5[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:25]=5[N:24]=4)[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42][NH2:43].[OH-:45].[Na+].OO>CS(C)=O.C(O)C>[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42][NH:43][C:2]1[CH:9]=[C:8]([N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([C:23]4[NH:27][C:26]5[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:25]=5[N:24]=4)[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:7]=[CH:6][C:3]=1[C:4]([NH2:5])=[O:45]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 66053N,N-DimethylethylenediamineHCID 583383582-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 58338244HCID 58338244, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The process is carried out as in stage 3 of Example 3, but using 300 mg of 2-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile, obtained according to stage 2 of Example 3, 296 mg of potassium carbonate and 1.259 g of N,N-dimethylethylenediamine in 3 ml of dimethyl sulphoxide. 1.357 ml of a 1M aqueous solution of sodium hydroxide, 1.313 ml of a 30% aqueous solution of hydrogen peroxide and 7 ml of ethanol are then added to the reaction medium. After treatment as in stage 3 of Example 3, and then purification by flash chromatography on silica gel, elution being carried out with mixtures of dichloromethane and a 7M solution of ammonia in methanol (from 95/5 to 90/10 by volume), followed by crystallization from 10 ml of diisopropyl ether, 200 mg of 2-(2-dimethylaminoethylamino)-4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]benzamide are thus obtained in the form of a beige solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. customAfter treatment as in stage 3 of Example 3, and then purification by flash chromatography
  3. washon silica gel, elution
  4. customa 7M solution of ammonia in methanol (from 95/5 to 90/10 by volume), followed by crystallization from 10 ml of diisopropyl ether, 200 mg of 2-(2-dimethylaminoethylamino)-4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]benzamide
  5. customare thus obtained in the form of a beige solid

Sources & evidence

ORD record
ord-503b7bda7db54716b97ba01cc57356e3
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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