Sodium Methoxide → HCID 54581425, compound

HRID 899960Notes

Reaction equation

HRID 899960 reaction equation
[CH3:1][C:2]1([CH3:31])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14]C(=O)C)[CH:9]=2)[C:5](=[O:18])[N:4]([C:19]2[CH:24]=[CH:23][C:22]([S:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)[C:3]1=[O:30].C[O-].[Na+]>CO>[NH2:14][C:10]1[CH:9]=[C:8]([CH2:7][N:6]2[C:2]([CH3:31])([CH3:1])[C:3](=[O:30])[N:4]([C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[C:5]2=[O:18])[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 52918127HCID 52918127, compound

Product 1

HCID 54581425HCID 54581425, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

500 mg (1.11 mmol) of N-{4-[5,5-dimethyl-2,4-dioxo-3-(4-trifluoromethylsulfanylphenyl)imidazolidin-1-ylmethyl]pyrid-2-yl}acetamide are dissolved in MeOH, 1.5 mmol of NaOMe are added and the resulting mixture is refluxed for 4 hours. The solvent is removed, the residue is taken up in CH2Cl2 and washed twice with 10% NaHCO3 solution and with water, and the organic phase is evaporated off. 340 mg (75%) of 1-(2-aminopyrid-4-ylmethyl)-5,5-dimethyl-3-(4-trifluoromethylsulfanylphenyl)imidazolidine-2,4-dione are isolated in this manner.

Workup

  1. temperaturethe resulting mixture is refluxed for 4 hours
  2. customThe solvent is removed
  3. washwashed twice with 10% NaHCO3 solution and with water
  4. customthe organic phase is evaporated off

Sources & evidence

ORD record
ord-8ae43d83209e49479399b6fb64aff6f0
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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