2-(Ethoxymethylene)propanedinitrile → 5-Amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-1h-pyrazole-4-carbonitrile

HRID 1378668Notes

Reaction equation

HRID 1378668 reaction equation
[Cl:1][C:2]1[C:3]([NH:11][NH2:12])=[N:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=12.C(O[CH:16]=[C:17]([C:20]#[N:21])[C:18]#[N:19])C>C(O)C>[NH2:21][C:20]1[N:11]([C:3]2[C:2]([Cl:1])=[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][N:5]3[N:4]=2)[N:12]=[CH:16][C:17]=1[C:18]#[N:19]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 545487483-Chloro-2-hydrazino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine

Product 1

HCID 153764335-Amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-1h-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.1 g (5.92 mmole) 3-Chloro-2-hydrazino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine and 0.72 g (5.92 mmole) ethoxymethylenemalononitrile in 10 ml ethanol was heated at reflux for 2 hours. The resulting precipitate was suction filtered, washed with ethanol, dried and purified by silica gel column chromatography (hexane/ethyl acetate).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationfiltered
  3. washwashed with ethanol
  4. customdried
  5. custompurified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fb967d5ddbdb424a956d3f923dffde6d
Source dataset
uspto-grants-1997_09
Patent number
US05668278

Reaction notes

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