Sodium Bicarbonate → 3-ethylsulfanyl-N-(4-trifluoromethoxyphenyl)picolinamide

HRID 713655ノート

反応式

HRID 713655 の反応式
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[CH2:13]([S:15][C:16]1[C:17]([C:22](O)=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:14].CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>C1C=CC2N(O)N=NC=2C=1.N1C=CC=CC=1>[CH2:13]([S:15][C:16]1[C:17]([C:22]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=2)=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:14]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 6008484-(Trifluoromethoxy)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 790069543-(Ethylsulfanyl)pyridine-2-carboxylic acid

生成物 1

HCID 1181133323-ethylsulfanyl-N-(4-trifluoromethoxyphenyl)picolinamide収率 89.2%

試薬・触媒・溶媒 2

HCID 757711-Hydroxybenzotriazole触媒HCID 1049Pyridine溶媒

実験手順

A mixture of 0.35 g of 4-trifluoromethoxyaniline, 0.36 g of 3-ethylsulfanylpicolinic acid, 0.46 g of EDCI hydrochloride, 0.02 g of HOBt and 3 mL of pyridine was stirred at room temperature overnight. A saturated aqueous sodium bicarbonate solution was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting solid was washed with hexane and dried to obtain 0.60 g of 3-ethylsulfanyl-N-(4-trifluoromethoxyphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 18).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washthe resulting solid was washed with hexane
  5. customdried

出典と根拠

ORDレコード
ord-8bf246cef7684967ad24936a9495a887
出典データセット
uspto-grants-2015_11
特許番号
US09185910B2

反応ノート

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