Hydrogen Peroxide → 2-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzamide

HRID 1877475Notes

Reaction equation

HRID 1877475 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][CH:37]=[C:38]([O:40][CH3:41])[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][CH:37]=[C:38]([O:40][CH3:41])[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]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 673080012-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile

Product 1

HCID 583382602-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

0.85 g of potassium carbonate and 3.14 ml of 3-amino-1-propanol are successively added to a solution of 0.81 g of 2-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile obtained in stage 2 of Example 27, in 7 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 1 hour and 20 minutes in a microwave, and then 20.9 ml of ethanol are added, followed by 4 ml of a 1N solution of sodium hydroxide and 4 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 trituration in diisopropyl ether, so as to give 0.45 g of 2-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-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 trituration in diisopropyl ether

Sources & evidence

ORD record
ord-7a2d93c0b66d446489f46204ffd507e2
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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