Ethane, 2-bromo-1,1-diethoxy- → HCID 9843102, compound

HRID 1955301Notes

Reaction equation

HRID 1955301 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][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)=[N:4][N:3]1[CH2:23][C:24](=[S:26])[NH2:25].[CH2:27](OC(OCC)CBr)[CH3:28]>CO.C(Cl)(Cl)Cl>[O:1]=[C:2]1[CH:7]=[CH:6][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)=[N:4][N:3]1[CH2:23][C:24]1[S:26][CH:27]=[CH:28][N:25]=1

Participants

5

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 10948415HCID 10948415, compound

Product 1

HCID 9843102HCID 9843102, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 3-(3-oxo-2-thiocarbamoylmethyl-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.50 g) and bromoacetaldehyde diethyl acetal (0.54 ml) in a mixture of methanol (2.5 ml) and chloroform (5 ml) was refluxed for 54 hours. After evaporating the solvent, the residue was chromatographed on silica gel (40 ml) using a mixture of chloroform and ethyl acetate (20:1). The desired fractions were collected and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 3-[3-oxo-2-(2-thiazolylmethyl)-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.23 g) as yellow needles.

Workup

  1. temperaturewas refluxed for 54 hours
  2. customAfter evaporating the solvent
  3. customthe residue was chromatographed on silica gel (40 ml)
  4. additiona mixture of chloroform and ethyl acetate (20:1)
  5. customThe desired fractions were collected
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-8c177ec203fb4c499387b915f49a19b8
Source dataset
uspto-grants-2000_09
Patent number
US06124456

Reaction notes

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