Hydrogen Peroxide → 2-[2-(1H-imidazol-1-yl)ethylamino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide

HRID 1877489Notes

Reaction equation

HRID 1877489 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[CH:24]=[N:25][C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)[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>[N:41]1([CH2:46][CH2:47][NH:48][C:2]2[CH:9]=[C:8]([N:10]3[C:22]4[CH:21]=[CH:20][CH:19]=[C:18]([C:23]5[CH:24]=[N:25][C:26]6[C:31]([CH:32]=5)=[CH:30][CH:29]=[CH:28][CH:27]=6)[C:17]=4[C:16]4[C:11]3=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:7]=[CH:6][C:3]=2[C:4]([NH2:5])=[O:49])[CH:45]=[CH:44][N:43]=[CH:42]1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 123779132-(Imidazol-1-yl)-ethylamine dihydrochlorideHCID 673078612-Fluoro-4-[4-(quinolin-3-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 583383202-[2-(1H-imidazol-1-yl)ethylamino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The process is carried out as in stage 3 of Example 3, but using 150 mg of 2-fluoro-4-[4-(quinolin-3-yl)carbazol-9-yl]benzonitrile, obtained according to stage 1 of Example 32, 150.5 mg of potassium carbonate, 1.336 g of 2-(1H-imidazol-1-yl)ethylamine dihydrochloride in 2 ml of dimethyl sulphoxide. 0.69 ml of a 1M aqueous solution of sodium hydroxide, 0.667 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 1 ml of ethyl acetate and 3 ml of diisopropyl ether, 130 mg of 2-[2-(1H-imidazol-1-yl)ethylamino]-4-[4-(quinolin-3-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. additionbeing carried out with a mixture of dichloromethane and ethanol (90/10 by volume)
  5. customfollowed by crystallization from 1 ml of ethyl acetate and 3 ml of diisopropyl ether, 130 mg of 2-[2-(1H-imidazol-1-yl)ethylamino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide
  6. customare thus obtained in the form of a beige solid

Sources & evidence

ORD record
ord-bc491b9032f14073a4e6bfd1f8a0c870
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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