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Hydrogen Peroxide → 2-[(3-hydroxypropyl)amino]-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzamide

HRID 1877482
Notes
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Reaction equation

HRID 1877482 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[NH2:7][CH2:8][CH2:9][CH2:10][OH:11].F[C:13]1[CH:20]=[C:19]([N:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([C:34]4[CH:35]=[N:36][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:39]=4)[C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].[OH-].[Na+].OO>CS(C)=O.O.C(O)C>[OH:11][CH2:10][CH2:9][CH2:8][NH:7][C:13]1[CH:20]=[C:19]([N:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([C:34]4[CH:35]=[N:36][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:39]=4)[C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:14]=1[C:15]([NH2:16])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 673087102-fluoro-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzonitrile

Product 1

HCID 58338356
2-[(3-hydroxypropyl)amino]-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

0.17 g of potassium carbonate and 0.64 ml of 3-amino-1-propanol are successively added to a solution of 0.18 g of 2-fluoro-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzonitrile in 2 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 1 hour 20 minutes in a microwave, and then 4.2 ml of ethanol are added, followed by 0.8 ml of a 1N solution of sodium hydroxide and 0.8 ml of 30% aqueous hydrogen peroxide. The reaction mixture is stirred at ambient temperature for 2 hours and then diluted with distilled water. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with water and a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The white solid obtained is purified by silica gel chromatography, elution being carried out with a mixture of dichloromethane, acetonitrile and methanol (96/2/2 by volume) so as to give 24 mg of 2-[(3-hydroxypropyl)amino]-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzamide in the form of a white solid, the characteristics of which are the following

Workup

  1. extractionThe aqueous phase is extracted twice with ethyl acetate
  2. washthe combined organic phases are washed with water
  3. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe white solid obtained
  6. customis purified by silica gel chromatography, elution
  7. additionbeing carried out with a mixture of dichloromethane, acetonitrile and methanol (96/2/2 by volume) so as

Sources & evidence

ORD record
ord-f90fb428c9194e929b6d6ee9c3aa5867
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309721B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes