3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]-N-(2-oxoethyl)benzamide → 6-(3,5-difluorophenyl)-2-(3-oxazol-2-ylbenzyl)-2H-pyridazin-3-one

HRID 467508Notes

Reaction equation

HRID 467508 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH2:16][C:17]3[CH:18]=[C:19]([CH:26]=[CH:27][CH:28]=3)[C:20]([NH:22][CH2:23][CH:24]=O)=[O:21])[N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.COC(NS([N+](CC)(CC)CC)(=O)=O)=O.C[N+](CC(O)=O)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH2:16][C:17]3[CH:28]=[CH:27][CH:26]=[C:19]([C:20]4[O:21][CH:24]=[CH:23][N:22]=4)[CH:18]=3)[N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 584972493-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]-N-(2-oxoethyl)benzamideHCID 86658973(Methoxycarbonylsulfamoyl)triethylammonium betaine

Product 1

HCID 584972536-(3,5-difluorophenyl)-2-(3-oxazol-2-ylbenzyl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.01 g (2.64 mmol) of 3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]-N-(2-oxoethyl)benzamide and 1.26 g (5.27 mmol) of (methoxycarbonylsulfamoyl)triethylammonium betaine (Burgess reagent) in 5.3 ml of THF is stirred at a temperature of 150° C. in a sealed vessel for 5 minutes. The reaction mixture is partitioned between saturated sodium hydrogencarbonate solution and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent, giving 6-(3,5-difluorophenyl)-2-(3-oxazol-2-ylbenzyl)-2H-pyridazin-3-one as colourless crystals; ESI 366.

Workup

  1. customThe reaction mixture is partitioned between saturated sodium hydrogencarbonate solution and dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-c633d1c528954f0e942484e7e623ae16
Source dataset
uspto-grants-2014_01
Patent number
US08623870B2

Reaction notes

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