Cyanoacetamide → HCID 22452602, compound

HRID 2185835Notes

Reaction equation

HRID 2185835 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[O-]CC.[Na+].CN([CH:14]=[C:15]([C:28]1[CH:33]=[CH:32][N:31]=[C:30]([S:34][CH3:35])[N:29]=1)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)=O)C>C(O)C>[CH3:35][S:34][C:30]1[N:29]=[C:28]([C:15]2[CH:14]=[C:3]([C:1]#[N:2])[C:4](=[O:5])[NH:6][C:16]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:33]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 2723922Sodium ethoxideHCID 68444917HCID 68444917, compound

Product 1

HCID 22452602HCID 22452602, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a mixture of cyanoacetamide (1.42 gm, 0.0169 mole) in ethanol (20 mL) was added a solution of sodium ethoxide (6.3 mL, 21 wt % solution, 0.0169 mole) in ethanol. The mixture was stirred for 5 minutes and dimethylamino-2-(2-methylsulfanylpyrimidin-4-yl)-1-(3-trifluoromethylphenyl)-prop-2-en-1-one (5.88 gm, 0.0160 mole) in ethanol (40 mL) added. The reaction was stirred for 18 hrs at room temperature and then concentrated to an oil. The oil was dissolved in ethyl acetate (50 mL) and water (50 mL) and the pH adjusted to 5.0 with a 10% solution of sodium hydrogen sulfate. The ethyl acetate layer was removed, dried over sodium sulfate, and concentrated to an oil. The oil was chromatographed on silica eluting with 5% acetone/dichloromethane to give 4.0 gm (68%) of the title compound as an oil.

Workup

  1. stirringThe reaction was stirred for 18 hrs at room temperature
  2. concentrationconcentrated to an oil
  3. dissolutionThe oil was dissolved in ethyl acetate (50 mL)
  4. customThe ethyl acetate layer was removed
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to an oil
  7. customThe oil was chromatographed on silica eluting with 5% acetone/dichloromethane

Sources & evidence

ORD record
ord-a4b9f6e54f4b4a1aa6eceff804653c7c
Source dataset
uspto-grants-2002_06
Patent number
US06403596B1

Reaction notes

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