Ethyl Acetate → N-[5,6-bis[4-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide

HRID 497698ノート

反応式

HRID 497698 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:34]=[C:35]4[C:39](=[CH:40][C:41]=3[C:42]3[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)=[CH:44][CH:43]=3)[N:38](COCC[Si](C)(C)C)[N:37]=[C:36]4[NH:64][C:65](=[O:69])[CH2:66][CH2:67][CH3:68])=[CH:29][CH:28]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>O1CCCC1>[C:19]1([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:34]=[C:35]4[C:39](=[CH:40][C:41]=3[C:42]3[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]5[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=5)=[CH:44][CH:43]=3)[NH:38][N:37]=[C:36]4[NH:64][C:65](=[O:69])[CH2:66][CH2:67][CH3:68])=[CH:29][CH:28]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 22319504N-[5,6-bis[4-(phenylmethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-indazol-3-yl]butanamide

生成物 1

HCID 22319668N-[5,6-bis[4-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

16.3 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 1.9 g of N-[5,6-bis[4-(phenylmethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-indazol-3-yl]butanamide, described previously, in 100 cm3 of tetrahydrofuran. The medium is then refluxed for 18 hours and is then allowed to return to room temperature and 100 cm3 of ethyl acetate are added; the organic phase is washed with 2×100 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 100 cm3 of saturated aqueous sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure (2 kPa; 50° 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 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); the residue is taken up in 25 cm3 of diisopropyl ether, filtered off on a sinter funnel and washed with 2×20 cm 3 of diisopropyl ether. After drying under reduced pressure (90 Pa; 50° C.), 700 mg of N-[5,6-bis[4-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide are obtained in the form of white crystals melting at 140° C.

後処理

  1. temperatureThe medium is then refluxed for 18 hours
  2. customto return to room temperature
  3. washthe organic phase is washed with 2×100 cm3 of saturated aqueous sodium hydrogen carbonate solution
  4. customThe organic phase is separated out
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure (2 kPa; 50° 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 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. filtrationfiltered off on a sinter funnel
  13. washwashed with 2×20 cm 3 of diisopropyl ether
  14. dry with materialAfter drying under reduced pressure (90 Pa; 50° C.), 700 mg of N-[5,6-bis[4-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide

出典と根拠

ORDレコード
ord-c49d31657e284a9cb30893a7944ab4a7
出典データセット
uspto-grants-2005_09
特許番号
US06949579B2

反応ノート

読み込み中…