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

HRID 533660ノート

反応式

HRID 533660 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
95 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cd2ed6b2e12143f19e7fedbe820a8f9e
出典データセット
uspto-grants-2014_10
特許番号
US08853238B2

反応ノート

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