Dimethylformamide → HCID 68358103, compound

HRID 1406004Notes

Reaction equation

HRID 1406004 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:15]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19](=[O:24])[C:16]=2[NH:17][N:18]=1)=[O:13])[CH3:2].[CH3:25]N(C=O)C.CI>CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:15]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19](=[O:24])[C:16]=2[N:17]([CH3:25])[N:18]=1)=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 178436232HCID 178436232, compound

Product 1

HCID 68358103HCID 68358103, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2,6-diethylphenyl)-8-oxo-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide (1.04 g, 3.211 mmol) in DMF (12 mL) Cs2CO3 (1.255 g, 3.85 mmol) and methyl iodide (0.22 mL, 3.532 mmol) were added. The reaction was stirred at room temperature for 1 h, then AcOEt (60 mL) was added and the organic phase washed with water (3×50 mL). The organic fraction was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (eluant: AcOEt/hexane 1/9) provided 0.99 g (91% yield) of the title compound as a white solid.

Workup

  1. washthe organic phase washed with water (3×50 mL)
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (eluant: AcOEt/hexane 1/9)

Sources & evidence

ORD record
ord-30c2bef9b6b54858a0e5a74e63304c1e
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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