Hydrogen Peroxide → 4-{4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazol-9-yl}-2-[(3-hydroxypropyl)amino]benzamide

HRID 1877479Notes

Reaction equation

HRID 1877479 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[NH2:7][CH2:8][CH2:9][CH2:10][OH:11].[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([C:26]2[C:38]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]([C:39]4[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41](F)[CH:40]=4)[C:30]=3[CH:29]=[CH:28][CH:27]=2)[CH:23]=[N:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].OO>CS(C)=O.O.C(O)C>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([C:26]2[C:38]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]([C:39]4[CH:46]=[CH:45][C:42]([C:43]([NH2:44])=[O:2])=[C:41]([NH:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:40]=4)[C:30]=3[CH:29]=[CH:28][CH:27]=2)[CH:23]=[N:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 673091964-{4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazol-9-yl}-2-fluorobenzonitrile

Product 1

HCID 583382244-{4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazol-9-yl}-2-[(3-hydroxypropyl)amino]benzamideYield 45.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

0.47 g of potassium carbonate and 1.7 g of 3-amino-1-propanol are successively added to a solution of 0.55 g of 4-{4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazol-9-yl}-2-fluorobenzonitrile, obtained in stage 3 of Example 67, in 6 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 1 hour 20 minutes in a microwave, and then 11.5 ml of ethanol are added, followed by 2.2 ml of a 1N solution of sodium hydroxide and 2.2 ml of 30% aqueous hydrogen peroxide. The reaction mixture is stirred at ambient temperature for 1 hour 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, and the residue is triturated with dichloromethane and diisopropyl ether, so as to give 0.29 g of 4-{4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazol-9-yl}-2-[(3-hydroxypropyl)amino]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 residue is triturated with dichloromethane and diisopropyl ether

Sources & evidence

ORD record
ord-e9e1eae0b13b40e7a5bfaae3ec3566bf
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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