Diethyl Pyrocarbonate → 2-[(4-fluorophenyl)sulfonyl-ethyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

HRID 1479809

反応式

HRID 1479809 の反応式
[CH2:1]([N:3]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4](=[CH2:8])[C:5]([OH:7])=O)[CH3:2].CCOC(OC(OCC)=O)=O.[F:30][C:31]([F:48])([F:47])[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[C:43]([CH2:45][NH2:46])[CH:42]=[CH:41][N:40]=2)=[CH:35][CH:34]=1>C1COCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([N:3]([CH2:1][CH3:2])[C:4](=[CH2:8])[C:5]([NH:46][CH2:45][C:43]2[CH:42]=[CH:41][N:40]=[C:39]([C:36]3[CH:35]=[CH:34][C:33]([O:32][C:31]([F:48])([F:30])[F:47])=[CH:38][CH:37]=3)[CH:44]=2)=[O:7])(=[O:11])=[O:10])=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 68759664HCID 68759664、化合物HCID 90384201HCID 90384201、化合物

生成物 1

HCID 783199092-[(4-fluorophenyl)sulfonyl-ethyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of acid 4B (0.25 g, 1 mmol) in THF (20 mL) was added with DEPC (0.17 mL, 1.3 mol eq) and the mixture was stirred at room temperature for about 5 minutes. Then [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (0.27 g, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was suspended in EtOAc (30 mL) and washed with water (50 mL) and brine. The separated organic phase, after drying over Na2SO4, was evaporated under reduced pressure and the residue purified by flash chromatography (7:3 EtOAc:Petroleum ether) to afford a pale orange solid (0.12 g) after crystallization from a mixture of diethyl ether/petroleum ether.

後処理

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water (50 mL) and brine
  4. dry with materialThe separated organic phase, after drying over Na2SO4
  5. customwas evaporated under reduced pressure
  6. customthe residue purified by flash chromatography (7:3 EtOAc:Petroleum ether)

出典と根拠

ORDレコード
ord-c6418437146b4e93902feaae00affdcb
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

関連ノート

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