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 467508노트

반응식

HRID 467508 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c633d1c528954f0e942484e7e623ae16
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623870B2

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