Hydrogen Peroxide → 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-[2-(1H-imidazol-1-yl)ethylamino]benzamide

HRID 1877487Notes

Reaction equation

HRID 1877487 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+].Cl.Cl.[N:41]1([CH2:46][CH2:47][NH2:48])[CH:45]=[CH:44][N:43]=[CH:42]1.[OH-:49].[Na+].OO>CS(C)=O.C(O)C.C(N(CC)CC)C>[F:32][C:29]1[CH:30]=[CH:31][C:25]2[N:24]=[C:23]([C:18]3[C:17]4[C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[N:10]([C:8]5[CH:7]=[CH:6][C:3]([C:4]([NH2:5])=[O:49])=[C:2]([NH:48][CH2:47][CH2:46][N:41]6[CH:45]=[CH:44][N:43]=[CH:42]6)[CH:9]=5)[C:22]=4[CH:21]=[CH:20][CH:19]=3)[NH:27][C:26]=2[CH:28]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 123779132-(Imidazol-1-yl)-ethylamine dihydrochlorideHCID 583383582-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 583383164-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-[2-(1H-imidazol-1-yl)ethylamino]benzamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

The process is carried out as in stage 3 of Example 3, but using 150 mg of 2-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile, obtained according to stage 2 of Example 3, 148 mg of potassium carbonate, 1.314 g of 2-(1H-imidazol-1-yl)ethylamine dihydrochloride and 1.445 g of triethylamine in 2 ml of dimethyl sulphoxide. 0.678 ml of a 1M aqueous solution of sodium hydroxide, 0.656 ml of a 30% aqueous solution of hydrogen peroxide and 3 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 a mixture of dichloromethane and ethanol (90/10 by volume), followed by crystallization from 2 ml of ethyl acetate, 130 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-[2-(1H-imidazol-1-yl)ethylamino]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. additionbeing carried out with a mixture of dichloromethane and ethanol (90/10 by volume)
  5. customfollowed by crystallization from 2 ml of ethyl acetate, 130 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-[2-(1H-imidazol-1-yl)ethylamino]benzamide
  6. customare thus obtained in the form of a beige solid

Sources & evidence

ORD record
ord-664f1a6c8cfa4202aacd1bccd2612f4a
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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