Sodium Carbonate → 2-ethylsulfanyl-N-(2-propylamino-5-trifluoromethylpyridin-3-yl)-benzamide

HRID 533660노트

반응식

HRID 533660 반응식
[CH2:1]([NH:4][C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1)[CH2:2][CH3:3].[CH2:16]([S:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22])[CH3:17].CCN=C=NCCCN(C)C.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[CH2:16]([S:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:11][C:10]1[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[N:6][CH:7]=[C:8]([C:12]([F:15])([F:13])[F:14])[CH:9]=1)=[O:22])[CH3:17]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 68091213N-propyl-5-trifluoromethylpyridin-2,3-diamine

생성물 1

HCID 679814212-ethylsulfanyl-N-(2-propylamino-5-trifluoromethylpyridin-3-yl)-benzamide수율 31.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
95 °C

실험 절차

A mixture of N-propyl-5-trifluoromethylpyridin-2,3-diamine (770 mg), 2-ethylsulfanyl-benzoic acid (700 mg), WSC (740 mg), and pyridine (20 ml) was stirred with heating at 95° C. for 7 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 422 mg of 2-ethylsulfanyl-N-(2-propylamino-5-trifluoromethylpyridin-3-yl)-benzamide (Compound (1B)-513).

후처리

  1. temperatureInto the reaction mixture cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cd2ed6b2e12143f19e7fedbe820a8f9e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853238B2

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