Methyl iodide → HCID 70664976, compound

HRID 1854534Notes

Reaction equation

HRID 1854534 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:7]=1)=[O:5])C.C(=O)([O-])[O-].[Cs+].[Cs+].IC.[OH-].[Na+]>CC(C)=O>[CH3:14][C:13]([CH3:16])([CH3:15])[C:12]([NH:11][C:9]1[N:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1)=[O:17]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 70664958HCID 70664958, compound

Product 1

HCID 70664976HCID 70664976, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

250 mg (0.8 mmol) of 5-(2,2-Dimethyl-propionylamino)-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester are dissolved in 10 ml of acetone, 1.0 g (3.2 mmol, 4 eq) of caesiumcarbonate and 225 mg (1.6 mmol, 2 eq) of iodomethane are added and the resulting mixture is stirred overnight at RT. The mixture is filtrated, the solvent removed in vacuo and the crude product dissolved in 10 ml of ethanol and stirred overnight at RT after the addition of 1.6 ml (2 eq) of 1N NaOH solution. After evaporation of the solvent the residue is taken up in a mixture of 10 ml CH2Cl2 and 10 ml 0.1N HCl, the organic phase is separated, dried over Na2SO4 and the solvent removed in vacuo yielding 75 mg (31%) of 5-(2,2-Dimethyl-propionylamino)-1-phenyl-1H-pyrazole-3-carboxylic acid. This material is used in the amide coupling steps.

Workup

  1. filtrationThe mixture is filtrated
  2. customthe solvent removed in vacuo
  3. dissolutionthe crude product dissolved in 10 ml of ethanol
  4. stirringstirred overnight at RT
  5. customAfter evaporation of the solvent the residue
  6. additionis taken up in a mixture of 10 ml CH2Cl2 and 10 ml 0.1N HCl
  7. customthe organic phase is separated
  8. dry with materialdried over Na2SO4
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ac54691a05ef4e039ba0c6897f6b3159
Source dataset
uspto-grants-2015_02
Patent number
US08962671B2

Reaction notes

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