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Ethyl Acetate → N-(6-(pyridin-4-yl)-1H-indazol-3-yl)butyramide

HRID 497642
ノート
印刷プレビュー

反応式

HRID 497642 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:33]=[C:32]3[C:28]([C:29]([NH:42][C:43](=[O:47])[CH2:44][CH2:45][CH3:46])=[N:30][N:31]3COCC[Si](C)(C)C)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[N:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:33]=[C:32]3[C:28]([C:29]([NH:42][C:43](=[O:47])[CH2:44][CH2:45][CH3:46])=[N:30][NH:31]3)=[CH:27][CH:26]=2)=[CH:23][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 22319546N-[6-(4-pyridyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide

生成物 1

HCID 10085059N-(6-(pyridin-4-yl)-1H-indazol-3-yl)butyramide

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
67 °C

実験手順

4.1 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 280 mg of N-[6-(4-pyridyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 20 cm3 of tetrahydrofuran, the medium is maintained at 67° C. for 17 hours and is then allowed to return to room temperature to add 50 cm3 of ethyl acetate and 50 cm3 of saturated aqueous sodium hydrogen carbonate solution. The organic phase is washed with 50 cm3 of saturated aqueous sodium chloride solution and then with 50 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 45° C.). The residue is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2 cm), eluting with ethyl acetate. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure (2 kPa; 50° C.). The residue is taken up in 10 cm3 of diisopropyl ether, filtered off on a sinter funnel and then washed successively with 5 cm3 of ethyl acetate and with 10 cm3 of diisopropyl ether. After drying (90 Pa; 50° C.), 60 mg of N-[6-(4-pyridyl)-1H-indazol-3-yl]butanamide are obtained in the form of a white solid melting at 200° C.

後処理

  1. customto return to room temperature
  2. washThe organic phase is washed with 50 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialwith 50 cm3 of water, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2 kPa; 45° C.)
  6. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  7. washon a column of silica gel (particle size 40-60 μm; diameter 2 cm), eluting with ethyl acetate
  8. additionThe fractions containing the expected product
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  10. filtrationfiltered off on a sinter funnel
  11. washwashed successively with 5 cm3 of ethyl acetate and with 10 cm3 of diisopropyl ether
  12. dry with materialAfter drying (90 Pa; 50° C.), 60 mg of N-[6-(4-pyridyl)-1H-indazol-3-yl]butanamide

出典と根拠

ORDレコード
ord-3ceb2aa9059947a8a9200c210c00804b
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949579B2

反応ノート

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