Ethyl Acetate → N-[6-chloro-5-(4-pyridyl)-1H-indazol-3-yl]butanamide

HRID 497690ノート

反応式

HRID 497690 の反応式
[F-].C([N+:6](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([NH:37][C:38](=[O:42])[CH2:39][CH2:40][CH3:41])=[N:25][N:26]2COCC[Si](C)(C)C)=[CH:22][C:21]=1[C:43]1[CH:48]=[CH:47]C([N+]([O-])=O)=[CH:45][CH:44]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([NH:37][C:38](=[O:42])[CH2:39][CH2:40][CH3:41])=[N:25][NH:26]2)=[CH:22][C:21]=1[C:43]1[CH:44]=[CH:45][N:6]=[CH:47][CH:48]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 22319608N-[6-chloro-5-(4-nitrophenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide

生成物 1

HCID 22319680N-[6-chloro-5-(4-pyridyl)-1H-indazol-3-yl]butanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

36.8 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 3 g of N-[6-chloro-5-(4-nitrophenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 135 cm3 of tetrahydrofuran. The medium is then refluxed for 18 hours and is then allowed to return to room temperature to add 100 cm3 of ethyl acetate and 75 cm3 of saturated aqueous sodium hydrogen carbonate solution. The organic phase is separated out after settling of the phases has taken place, washed with 100 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 100 cm3 of saturated sodium chloride solution, 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 a cyclohexane/ethyl acetate mixture (80/20 by volume). 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 35 cm3 of diisopropyl ether, filtered off on a sinter funnel and then washed with 2×20 cm3 of diisopropyl ether. After drying (90 Pa; 50° C.), 88 mg of N-[6-chloro-5-(4-nitrophenyl)-1H-indazol-3-yl]butanamide are obtained in the form of yellow crystals melting at 260° C.

後処理

  1. temperatureThe medium is then refluxed for 18 hours
  2. customto return to room temperature
  3. customThe organic phase is separated out
  4. washwashed with 100 cm3 of saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialwith 100 cm3 of saturated sodium chloride solution, dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa; 45° C.)
  8. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  9. washon a column of silica gel (particle size 40-60 μm; diameter 2 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume)
  10. additionThe fractions containing the expected product
  11. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  12. filtrationfiltered off on a sinter funnel
  13. washwashed with 2×20 cm3 of diisopropyl ether
  14. dry with materialAfter drying (90 Pa; 50° C.), 88 mg of N-[6-chloro-5-(4-nitrophenyl)-1H-indazol-3-yl]butanamide

出典と根拠

ORDレコード
ord-e40f4b09819848a694077dc60b6b9ba7
出典データセット
uspto-grants-2005_09
特許番号
US06949579B2

反応ノート

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