Methanol → HCID 10499639, compound

HRID 465998Notes

Reaction equation

HRID 465998 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][NH:3]1.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].[OH-].C[N+](C)(C)CC1C=CC=CC=1.CO>C(Cl)(Cl)Cl>[CH3:28][O:27][C:23]([CH2:24][CH2:25][N:3]1[C:2](=[O: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]1)=[O:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

Product 1

HCID 10499639HCID 10499639, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.43 g), methyl acrylate (1.29 g), 40% methanolic trimethylbenzylammonium hydroxide (0.4 ml) and methanol (2 ml) in chloroform (8 ml) was refluxed for 40 minutes and then evaporated in vacuo. To the residue were added methylene chloride (30 ml) and water (30 ml), and the organic layer was separated, dried over magnesium sulfate and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of ethyl acetate and diethyl ether to give 3-[2-(2-methoxycarbonylethyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.37 g).

Workup

  1. temperaturewas refluxed for 40 minutes
  2. customevaporated in vacuo
  3. additionTo the residue were added methylene chloride (30 ml) and water (30 ml)
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-163aed4fd77d4d66a74441e6ad6e4b36
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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