Hydrogen Peroxide → HCID 59729943, compound

HRID 492336Notes

Reaction equation

HRID 492336 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=2)=[C:13]([CH3:26])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.C([O-])([O-])=[O:30].[K+].[K+]>CS(C)=O>[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]([NH2:21])=[O:30])=[CH:18][N:17]=2)=[C:13]([CH3:26])[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 59730056HCID 59730056, compound

Product 1

HCID 59729943HCID 59729943, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine nitrile, 6-[4-(2-benzylamino-ethyl)-2-methyl-phenoxy]-nicotinonitrile (compound of example 219, step 3) (13 mg, 0.04 mmol), H2O2 (5 μL) and K2CO3 (3 mg, 0.02 mmol) in DMSO (0.2 mL), and stir the mixture at room temperature overnight. Add water and extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4 and eliminate the solvent. Purify by flash chromatography (eluent: CHCl3/0.5% EtOH/0.05% NH4OH) to give the title compound (7 mg, 52%). Electrospray MS M+1 ion=362. 1H-NMR (methanol-d4, 300 MHz): 8.59 (d, 1H, J=2.5 Hz), 8.24 (dd, 1H, J=2.5 and 8.0 Hz), 7.33-7.21 (m, 5H), 7.15-7.07 (m, 2H), 6.98-6.93 (m, 2H), 3.78 (s, 2H), 2.83 (s, 4H), 2.09 (s, 3H).

Workup

  1. extractionAdd water and extract the aqueous layer with EtOAc
  2. dry with materialDry the organic layer over Na2SO4
  3. customPurify by flash chromatography (eluent: CHCl3/0.5% EtOH/0.05% NH4OH)

Sources & evidence

ORD record
ord-df2c87e8321147a2912c8346911f06a8
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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