Hydrogen Peroxide → 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(4-hydroxybutan-3(R,S)-ylamino)benzamide

HRID 1877460

Reaction equation

HRID 1877460 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:33](=[O:36])([O-])[O-].[K+].[K+].[OH-:39].[Na+].OO>CS(C)=O.C(O)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:39])=[C:2]([NH:5][CH:4]([CH2:33][OH:36])[CH2:3][CH3:2])[CH:9]=5)[C:22]=4[CH:21]=[CH:20][CH:19]=3)[NH:27][C:26]=2[CH:28]=1

Participants

7

Reactant 4

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

Product 1

HCID 686394714-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(4-hydroxybutan-3(R,S)-ylamino)benzamide

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 1.273 g of 3(R,S)-aminopropanol 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, then purification by flash chromatography on silica gel, elution being carried out with a mixture of dichloromethane and ethanol (95/5 by volume), followed by crystallization from 10 ml of diisopropyl ether, 165 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(4-hydroxybutan-3(R,S)-ylamino)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, then purification by flash chromatography
  3. washon silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and ethanol (95/5 by volume)
  5. customfollowed by crystallization from 10 ml of diisopropyl ether, 165 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(4-hydroxybutan-3(R,S)-ylamino)benzamide
  6. customare thus obtained in the form of a beige solid

Sources & evidence

ORD record
ord-961315c2db1d40a0b16752e3c8b3d7f5
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Linked notes

Loading…