Water → 5-Amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-4-thioacetylpyrazole

HRID 1080382Notes

Reaction equation

HRID 1080382 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7]([C:10]2[C:18]([Cl:19])=[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][N:12]3[N:11]=2)[C:8]=1[NH2:9])(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1.O>C(COC)OC>[NH2:9][C:8]1[N:7]([C:10]2[C:18]([Cl:19])=[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][N:12]3[N:11]=2)[N:6]=[CH:5][C:4]=1[C:1](=[S:29])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 543782934-Acetyl-5-amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)pyrazole

Product 1

HCID 540968095-Amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-4-thioacetylpyrazole

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

0.28 g (1 mmol) 4-Acetyl-5-amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)pyrazole was dissolved in 5 ml dimethoxyethane and treated with 0.28 (0.6 mmol) Lawesson's reagent. After heating under reflux for 2 hours with stirring, the reaction solution was poured into water and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography. (Hexane/ethyl acetate 1:1).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43b9d8af01564e678be6ae60f247a555
Source dataset
uspto-grants-1996_12
Patent number
US05580986

Reaction notes

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