Cyanoacetamide → 3-(3-Cyano-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 703975Notes

Reaction equation

HRID 703975 reaction equation
CN([CH:4]=[C:5]([C:8]1[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12)[CH:6]=O)C.[C:23]([CH2:25][C:26]([NH2:28])=[O:27])#[N:24].[O-]CC.[Na+].C(OC(=O)C)(=O)C>O.C(O)C>[C:23]([C:25]1[C:26](=[O:27])[NH:28][CH:4]=[C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:6]=1)#[N:24]

Participants

7

Reactant 4

HCID 7898CyanoacetamideHCID 7918Acetic AnhydrideHCID 2723922Sodium ethoxideHCID 543639333-(N,N-dimethylamino)-2-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylaldehyde

Product 1

HCID 151581163-(3-Cyano-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridineYield 48.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(N,N-dimethylamino)-2-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylaldehyde (cis and trans mixture) (4.00 g), 2-cyanoacetamide (2.31 g), sodium ethoxide (4.67 g) and ethanol (40 ml) was refluxed for 2 hours. After cooling the reaction mixture was added acetic anhydride (24 ml) and water (120 ml) and stirred at room temperature. The resultant precipitates were collected and recrystallized from a mixture of N,N-dimethylformamide and water to give 3-(3-cyano-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.08 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling the reaction mixture
  3. customThe resultant precipitates
  4. customwere collected
  5. customrecrystallized from a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-afbf8ac3c7e945dba25458be73845971
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

Loading…