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1,3-Oxazole-4-carbonyl chloride → N-[6-(3-{[3-(1-cyano-1-methylethyl)benzoyl]amino}-4-methylphenoxy)-1,3-benzothiazol-2-yl]-1,3-oxazole-4-carboxamide

HRID 2190382
ノート
印刷プレビュー

反応式

HRID 2190382 の反応式
[O:1]1[CH:5]=[C:4]([C:6](Cl)=[O:7])[N:3]=[CH:2]1.[NH2:9][C:10]1[S:11][C:12]2[CH:18]=[C:17]([O:19][C:20]3[CH:21]=[CH:22][C:23]([CH3:40])=[C:24]([NH:26][C:27](=[O:39])[C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([C:37]#[N:38])([CH3:36])[CH3:35])[CH:29]=4)[CH:25]=3)[CH:16]=[CH:15][C:13]=2[N:14]=1>N1C=CC=CC=1>[C:37]([C:34]([C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[C:27]([NH:26][C:24]1[CH:25]=[C:20]([CH:21]=[CH:22][C:23]=1[CH3:40])[O:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([NH:9][C:6]([C:4]3[N:3]=[CH:2][O:1][CH:5]=3)=[O:7])[S:11][C:12]=2[CH:18]=1)=[O:39])([CH3:36])[CH3:35])#[N:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 142814311,3-Oxazole-4-carbonyl chlorideHCID 86646002N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

生成物 1

HCID 86655358N-[6-(3-{[3-(1-cyano-1-methylethyl)benzoyl]amino}-4-methylphenoxy)-1,3-benzothiazol-2-yl]-1,3-oxazole-4-carboxamide収率 29%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

1,3-Oxazole-4-carbonyl chloride synthesized above was suspended in pyridine (4.0 mL) at 0° C., N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (200 mg, 0.452 mmol) produced in Example A7(vi) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in methanol (4.0 mL). 1N Aqueous sodium hydroxide solution (4.0 mL) was added, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added 1N hydrochloric acid (10 mL), and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100), and the obtained solution was concentrated under reduced pressure. The residue was triturated with ethyl acetate/diisopropyl ether to give the title compound (70 mg, 29%) as a colorless solid.

後処理

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. addition1N Aqueous sodium hydroxide solution (4.0 mL) was added
  4. stirringthe mixture was stirred at room temperature for 30 min
  5. additionTo the reaction mixture was added 1N hydrochloric acid (10 mL)
  6. extractionthe mixture was extracted with ethyl acetate (100 mL)
  7. washThe organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL)
  8. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  12. concentrationthe obtained solution was concentrated under reduced pressure
  13. customThe residue was triturated with ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-7e537da0ed1b4126a47ffb7832654b9f
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324395B2

反応ノート

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