Hydrogen Peroxide → HCID 58338192, compound

HRID 1877523Notes

Reaction equation

HRID 1877523 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+].[CH3:39][N:40]1[CH:45]2[CH2:46][CH2:47][CH:41]1[CH2:42][CH:43]([NH2:48])[CH2:44]2.[OH-:49].[Na+].OO>CS(C)=O.C(O)C>[CH3:39][N:40]1[CH:45]2[CH2:46][CH2:47][CH:41]1[CH2:42][CH:43]([NH:48][C:2]1[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]=1[C:4]([NH2:5])=[O:49])[CH2:44]2

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 673078612-Fluoro-4-[4-(quinolin-3-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 58338192HCID 58338192, compound

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-(quinolin-3-yl)-9H-carbazol-9-yl]benzonitrile, obtained according to stage 1 of Example 32, 301 mg of potassium carbonate and 3 g of 8-methyl-8-azabicyclo[3.2.1]octan-3-amine in 1.7 ml of dimethyl sulphoxide, in a microwave for 1 hour and 15 minutes at 115° C. 1.38 ml (1.38 mmol) of a 1M aqueous solution of sodium hydroxide, 1.33 ml (13 mmol) of a 30% aqueous solution of hydrogen peroxide and 8 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 ammonia in a 7M solution in methanol (97/3 by volume), 150 mg of 2-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide are thus obtained in the form of an off-white 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 10 g of silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and ammonia in a 7M solution in methanol (97/3 by volume), 150 mg of 2-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide
  5. customare thus obtained in the form of an off-white solid

Sources & evidence

ORD record
ord-43a6e3b6181344479337a9d56ed7756a
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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