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

HRID 713665

반응식

HRID 713665 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 757711-Hydroxybenzotriazole촉매HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-acc110fd4c104b7da7e5a3017d460713
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09185910B2

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