2-(Ethoxymethylidene)-3-oxobutanenitrile → 4-Acetyl-5-amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)pyrazole

HRID 1291990Notes

Reaction equation

HRID 1291990 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](=[O:22])[CH3:21])[C:18]#[N:19])C>C(O)C>[C:20]([C:17]1[CH:16]=[N:12][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)[C:18]=1[NH2:19])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 534170282-(Ethoxymethylidene)-3-oxobutanenitrileHCID 545487483-Chloro-2-hydrazino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine

Product 1

HCID 543782934-Acetyl-5-amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.56 g (3 mmol) 3-Chloro-2-hydrazino-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridine was dissolved in 5 ml ethanol and treated with 0.42 g (3 mmol) 2-ethoxymethylen-3-oxobutyro-nitrile. After heating under reflux for 3 hours, the mixture was concentrated and the residue purified by silica gel chromatography (hexane/ethyl acetate 1:1).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. concentrationthe mixture was concentrated
  4. customthe residue purified by silica gel chromatography (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-fd87259a22a444858b3828e0f2baaa59
Source dataset
uspto-grants-1998_05
Patent number
US05756424

Reaction notes

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