Hydrogen Peroxide → 4-Chloro-3-{5-[(2-cyclohexylethylamino)methyl]pyridin-2-yl}benzamide

HRID 561362Notes

Reaction equation

HRID 561362 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:12][N:11]=1.C([O-])([O-])=[O:27].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[O:27])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 595448504-Chloro-3-[5-[(2-cyclohexylethylamino)methyl]pyridin-2-yl]benzonitrile

Product 1

HCID 252169684-Chloro-3-{5-[(2-cyclohexylethylamino)methyl]pyridin-2-yl}benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-chloro-3-{5-[(2-cyclohexylethylamino)methyl]pyridin-2-yl}benzonitrile (170 mg, 0.48 mmol) in DMSO (4 mL) was added K2CO3 (66 mg, 0.48 mmol) and 70% hydrogen peroxide (0.5 mL, 4.8 mmol). The mixture was stirred at rt for 5 h before water (5 mL) was added and the mixture partitioned between EtOAc (20 mL) and water (20 mL). The organic phase was washed with water (3×20 mL), brine (20 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (0.4% NH3: 4% MeOH: DCM) to give the title compound: RT=2.57 min; m/z (ES+)=372.2 [M+H]+.

Workup

  1. additionwas added
  2. customthe mixture partitioned between EtOAc (20 mL) and water (20 mL)
  3. washThe organic phase was washed with water (3×20 mL), brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by column chromatography (0.4% NH3: 4% MeOH: DCM)

Sources & evidence

ORD record
ord-747b4553461c414cb0372b649e292558
Source dataset
uspto-grants-2011_11
Patent number
US08063247B2

Reaction notes

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