Tetrahydrofuran → methyl 6,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)-phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-acetate

HRID 324302

反応式

HRID 324302 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][C:24](=[C:27]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[CH2:31][CH2:30][N:29]4[C:38]([CH:41]=O)=[CH:39][N:40]=[C:28]34)[CH2:23][CH2:22]2)=[CH:15][CH:14]=1.CSCS(C)=[O:47].C1[CH2:53][O:52][CH2:51]C1>[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][C:24](=[C:27]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[CH2:31][CH2:30][N:29]4[C:38]([CH2:41][C:51]([O:52][CH3:53])=[O:47])=[CH:39][N:40]=[C:28]34)[CH2:23][CH2:22]2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 99156646,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-carboxaldehyde

生成物 1

HCID 18612504methyl 6,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)-phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-acetate収率 30%

試薬・触媒・溶媒 1

HCID 66854Benzyltrimethylammonium hydroxide溶媒

実験手順

A mixture of compound 4 (8.32 g) and methyl methylthiomethyl sulfoxide (MMTS) (4.5 g) in THF (100 ml) and benzyltrimethyl ammonium hydroxide (40% in methanol; 20 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was taken up in water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. Toluene was added twice and evaporated again. The residue was taken up in methanol (50 ml). HCl gas was bubbled through the mixture, cooled on an ice bath, for 30 minutes. The mixture was stirred overnight. The solvent was evaporated. The residue was taken up in water, alkalized with K2CO3 and extracted with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 2.7 g (30%) of methyl 6,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-acetate (compound 5).

後処理

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. additionToluene was added twice
  9. customevaporated again
  10. customHCl gas was bubbled through the mixture
  11. temperaturecooled on an ice bath, for 30 minutes
  12. stirringThe mixture was stirred overnight
  13. customThe solvent was evaporated
  14. extractionextracted with DCM
  15. customThe organic layer was separated
  16. customdried
  17. filtrationfiltered
  18. customthe solvent was evaporated
  19. customThe residue was purified over silica gel on a glass
  20. filtrationfilter (eluent
  21. customThe pure fractions were collected
  22. customthe solvent was evaporated
  23. customThe residue was crystallized from ACN
  24. filtrationThe precipitate was filtered off
  25. customdried

出典と根拠

ORDレコード
ord-2a60eca8825846e4ba1403fa1e67efe3
出典データセット
uspto-grants-2001_04
特許番号
US06218381B1

関連ノート

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