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 467508ノート

反応式

HRID 467508 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c633d1c528954f0e942484e7e623ae16
出典データセット
uspto-grants-2014_01
特許番号
US08623870B2

反応ノート

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