1-Hydroxybenzotriazole → 3-ethylsulfanyl-N-(5-pentafluoroethylpyridin-2-yl)picolinamide

HRID 713668노트

반응식

HRID 713668 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH2:15]([S:17][C:18]1[C:19]([C:24](O)=[O:25])=[N:20][CH:21]=[CH:22][CH:23]=1)[CH3:16].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH2:15]([S:17][C:18]1[C:19]([C:24]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:14])([F:13])[C:9]([F:10])([F:11])[F:12])=[CH:4][N:3]=2)=[O:25])=[N:20][CH:21]=[CH:22][CH:23]=1)[CH3:16]

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 498535555-(Perfluoroethyl)pyridin-2-amineHCID 790069543-(Ethylsulfanyl)pyridine-2-carboxylic acid

생성물 1

HCID 1182059403-ethylsulfanyl-N-(5-pentafluoroethylpyridin-2-yl)picolinamide수율 29.4%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 0.63 g of 2-amino-5-pentafluoroethylpyridine, 0.55 g of 3-ethylsulfanylpicolinic acid, 1.0 g of EDCI hydrochloride, 0.04 g of HOBt and 5 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 residue was applied to a silica gel column chromatography to obtain 0.33 g of 3-ethylsulfanyl-N-(5-pentafluoroethylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 46).

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-2d266a5a559a4c53905211a28e46641b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09185910B2

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