Hydrogen Peroxide → 2-[(1-methyl-1H-pyrazol-4-yl)methylamino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide

HRID 1877504Notes

Reaction equation

HRID 1877504 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+].[NH2:39][CH2:40][C:41]1[CH:42]=[N:43][N:44]([CH3:46])[CH:45]=1.[OH-:47].[Na+].OO>CS(C)=O.C(O)C>[CH3:46][N:44]1[CH:45]=[C:41]([CH2:40][NH:39][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:47])[CH:42]=[N:43]1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 671225(1-methyl-1H-pyrazol-4-yl)methanamineHCID 673078612-Fluoro-4-[4-(quinolin-3-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 583382662-[(1-methyl-1H-pyrazol-4-yl)methylamino]-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 165.4 mg of 2-fluoro-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzonitrile, obtained according to stage 1 of Example 32, 165.8 mg of potassium carbonate and 356 mg of 4-aminomethyl-1-methyl-1H-pyrazole in 1.7 ml of dimethyl sulphoxide, in a microwave for 1 hour and 30 minutes at 115° C. 0.76 ml of a 1M aqueous solution of sodium hydroxide, 0.735 ml of a 30% aqueous solution of hydrogen peroxide and 4 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 10 g of silica gel, elution being carried out with a mixture of dichloromethane and methanol (95/5 by volume), 2-[(1-methyl-1H-pyrazol-4-yl)methylamino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide is thus obtained in the form of a white powder, 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 10 g of silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and methanol (95/5 by volume), 2-[(1-methyl-1H-pyrazol-4-yl)methylamino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide
  5. customis thus obtained in the form of a white powder

Sources & evidence

ORD record
ord-2ff84a4736ad43f186cc645da2b5a8ed
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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