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

HRID 1877465

Reaction equation

HRID 1877465 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-:34].[K+].[K+].Cl.[NH2:40][CH2:41][CH2:42][C:43]([NH2:45])=[O:44].[OH-].[Na+].OO>CS(C)=O.C(O)C.C(N(CC)CC)C>[C:43]([CH2:42][CH2:41][NH:40][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:34])(=[O:44])[NH2:45]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 222222883-Aminopropanamide hydrochlorideHCID 583383582-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 583382252-(2-carbamoylethylamino)-4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]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 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, 1.779 g of beta-alanineamide hydrochloride and 1.445 g of triethylamine 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 ethanol (from 95/5 to 90/10 by volume), followed by crystallization from 10 ml of diisopropyl ether, 200 mg of 2-(2-carbamoylethylamino)-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. customfollowed by crystallization from 10 ml of diisopropyl ether, 200 mg of 2-(2-carbamoylethylamino)-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-2e5969c61461401c8510aac5b16cb34a
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Linked notes

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