Dimethyl Sulfoxide → HCID 135899321, compound

HRID 2100469Notes

Reaction equation

HRID 2100469 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].CS(C)=O.OO.[C:13]([C:15]1[C:16]([NH:21][C:22](=O)[CH2:23][O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:17][CH:18]=[CH:19][CH:20]=1)#[N:14]>O.CO.C(OCC)(=O)C>[CH2:25]([O:24][CH2:23][C:22]1[NH:14][C:13](=[O:2])[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][C:16]=2[N:21]=1)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 68568667N-(3-cyano-pyridin-2-yl)-2-phenethyloxy-acetamide

Product 1

HCID 135899321HCID 135899321, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (1.22 g, 8.82 mmol), DMSO (0.44 ml), and hydrogen peroxide (0.9 ml of a 30% solution in H2O) were added to a suspension of N-(3-cyano-pyridin-2-yl)-2-phenethyloxy-acetamide (400 mg, 1.42 mmol) in methanol (6 ml). After 3 h at r.t., the mixture was taken up in ethyl acetate, and washed with salt. NH4Cl. The solution was dried (Na2SO4) and the solvent was evaporated. The residue was triturated with tert-butyl methyl ether to give the title compound. MS: m/e=280.4 [M−H−], 1H NMR (d6-DMSO): 2.91 (t, 2H), 3.78 (t, 2H), 4.45 (s, 2H), 7.17-7.22 (m, 5H), 7.53 (dd, 1H), 8.49 (d, 1H), 8.93 (d, 1H), 12.44 (bs, 1H).

Workup

  1. washwashed with salt
  2. dry with materialThe solution was dried (Na2SO4)
  3. customthe solvent was evaporated
  4. customThe residue was triturated with tert-butyl methyl ether

Sources & evidence

ORD record
ord-cb30b64b060a453780c2a8400f74ccf1
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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