Potassium Iodide → HCID 86681505, compound

HRID 1192821Notes

Reaction equation

HRID 1192821 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[OH:9][N:10]=[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:12]([NH:14][CH3:15])=[O:13].Cl[CH2:23][C:24]1[N:29]=[C:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=[CH:26][CH:25]=1>C(#N)C.CN(C=O)C>[CH3:15][NH:14][C:12](=[O:13])[C:11](=[N:10][O:9][CH2:23][C:24]1[N:29]=[C:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH:27]=[CH:26][CH:25]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 6400952HCID 6400952, compoundHCID 21851761tert-Butyl (6-(chloromethyl)pyridin-2-yl)carbamate

Product 1

HCID 86681505HCID 86681505, compound

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

37.4 g (114 mmol) of caesium carbonate and 0.91 g, (5.47 mmol) of potassium iodide were added to a solution of 10.7 g (60.1 mmol) of 2-(hydroxyimino)-N-methyl-2-phenylacetamide (81:19 mixture of the Z and E diastereoisomers) and 13.3 g (54.7 mmol) of tert-butyl [6-(chloromethyl)pyridin-2-yl]carbamate in 100 ml of acetonitrile: DMF 75:25. After stirring for 3 h at room temperature, the mixture was concentrated by evaporation in vacuo and the residue was admixed with 250 ml of ethyl acetate. Then, 500 ml of water were added, the phases were separated and the aqueous phase was extracted again with 250 ml of ethyl acetate. The combined organic phases were dried with MgSO4 and concentrated by evaporation in vacuo. This gave 16.8 g (95% purity; 89:11 mixture of Z and E isomers) of tert-butyl {6-[({[2-(methylamino)-2-oxo-1-phenylethylidene]amino}oxy)methyl]pyridin-2-yl}carbamate.

Workup

  1. concentrationthe mixture was concentrated by evaporation in vacuo
  2. additionThen, 500 ml of water were added
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted again with 250 ml of ethyl acetate
  5. dry with materialThe combined organic phases were dried with MgSO4
  6. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-83098e5c023d4086b122e33367fdd4a8
Source dataset
uspto-grants-2014_03
Patent number
US08680283B2

Reaction notes

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