Sodium Bicarbonate → 3-ethylsulfanyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide

HRID 713665

反応式

HRID 713665 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)([O:6][CH3:7])[O:4][CH3:5].[CH2:17]([S:19][C:20]1[C:21]([C:26](O)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=1)[CH3:18].CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>C1C=CC2N(O)N=NC=2C=1.N1C=CC=CC=1>[CH2:17]([S:19][C:20]1[C:21]([C:26]([NH:12][C:11]2[CH:13]=[CH:14][C:8]([C:3]([O:6][CH3:7])([O:4][CH3:5])[C:2]([F:15])([F:16])[F:1])=[CH:9][CH:10]=2)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=1)[CH3:18]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 790069543-(Ethylsulfanyl)pyridine-2-carboxylic acidHCID 1181134654-(2,2,2-Trifluoro-1,1-dimethoxyethyl)aniline

生成物 1

HCID 1181134133-ethylsulfanyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide収率 89.4%

試薬・触媒・溶媒 2

HCID 757711-Hydroxybenzotriazole触媒HCID 1049Pyridine溶媒

実験手順

A mixture of 0.38 g of 4-(2,2,2-trifluoro-1,1-dimethoxyethyl)aniline, 0.22 g of 3-ethylsulfanylpicolinic acid, 0.29 g of EDCI hydrochloride, 0.01 g of HOBt and 5 mL of pyridine was stirred at room temperature for 2 hours. 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 residue was applied to a silica gel column chromatography to obtain 0.43 g of 3-ethylsulfanyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide (Compound of Present Invention 58).

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

出典と根拠

ORDレコード
ord-acc110fd4c104b7da7e5a3017d460713
出典データセット
uspto-grants-2015_11
特許番号
US09185910B2

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