Thionyl Chloride → HCID 86746737, compound

HRID 1590624Notes

Reaction equation

HRID 1590624 reaction equation
OCCN1C(=O)C=CC([C:11]2[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=23)=N1.S(Cl)([Cl:28])=O>C(Cl)Cl>[ClH:28].[ClH:28].[C:20]1([C:12]2[CH:11]=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10496789HCID 10496789, compound

Product 1

HCID 86746737HCID 86746737, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[2-(2-hydroxyethyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.5 g) and thionyl chloride (0.13 ml) in methylene chloride (4 ml) was stirred at room temperature for 1 hour and evaporated in vacuo. To the residue was added dropwise a solution of 1-(2-hydroxyethyl)piperazine (0.78 g) in amyl alcohol (5 ml), and the suspension was refluxed for 1.5 hours. The reaction mixture was evaporated in vacuo, and the residue was purified by column chromatography on silica gel using chloroform as eluent. The obtained oil was treated with a 20% solution of hydrogen chloride in ethanol to afford 3-[2-{2-{4-(2-}ethyl}-3-oxo-2,3-hydroxyethyl)piperazin-1-yl}ethyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine dihydrochloride.

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added dropwise a solution of 1-(2-hydroxyethyl)piperazine (0.78 g) in amyl alcohol (5 ml)
  3. temperaturethe suspension was refluxed for 1.5 hours
  4. customThe reaction mixture was evaporated in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. additionThe obtained oil was treated with a 20% solution of hydrogen chloride in ethanol

Sources & evidence

ORD record
ord-0b2dc9b13ca74b1daad9555724c1f886
Source dataset
uspto-grants-1993_04
Patent number
US05204346

Reaction notes

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