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

HRID 713655노트

반응식

HRID 713655 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 1181133323-ethylsulfanyl-N-(4-trifluoromethoxyphenyl)picolinamide수율 89.2%

시약·촉매·용매 2

HCID 757711-Hydroxybenzotriazole촉매HCID 1049Pyridine용매

실험 절차

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).

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
  4. washthe resulting solid was washed with hexane
  5. customdried

출처 및 근거

ORD 기록
ord-8bf246cef7684967ad24936a9495a887
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09185910B2

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