Cyanoacetamide → HCID 178509481, compound

HRID 42558Notes

Reaction equation

HRID 42558 reaction equation
CN(C)[CH:3]=[C:4]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=O.[C:21]([CH2:23][C:24]([NH2:26])=[O:25])#[N:22].C[O-].[Na+]>CN(C=O)C>[F:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[C:4]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)=[CH:3][C:23]([C:21]#[N:22])=[C:24]([OH:25])[N:26]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 545188383-(Dimethylamino)-1-(4-fluorophenyl)-2-(pyridin-4-yl)prop-2-en-1-one

Product 1

HCID 178509481HCID 178509481, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(dimethylamino)-1-(4-fluorophenyl)-2-(4-pyridyl)prop-2-en-1-one (12.77 g, 47.2 mmol, obtained in reference example 7) in DMF (175 mL), 2-cyanoacetamide (4.41 g, 52.0 mmol) was added under argon atmosphere. Then, sodium methoxide (5.35 g, 99.2 mmol) was added and heated to reflux for 1 hour. The mixture was allowed to cool, concentrated and diluted with water. The pH was adjusted to 4 with 1 N HCl. A precipitate was obtained that was filtered and dried to give 6.57 g of the desired compound as a solid (yield: 48%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureto cool
  4. concentrationconcentrated
  5. additiondiluted with water
  6. customA precipitate was obtained
  7. filtrationthat was filtered
  8. customdried

Sources & evidence

ORD record
ord-79b1347b4062441e92fb2d83e41ea7f0
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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