Acetic Acid → Laniquidar

HRID 1264567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264567
[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:42])=[CH:39][N:40]=[C:28]34)[CH2:23][CH2:22]2)=[CH:15][CH:14]=1.[O-:43][C:44]#N.[Na+].C(O)(=O)C>CO.[O-2].[O-2].[Mn+4]>[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[CH2:22][CH2:23][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]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][N:40]=[C:28]34)[CH2:25][CH2:26]2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 517096Sodium CyanateHCID 99156646,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-carboxaldehyde

Produkt 1

HCID 6450806LaniquidarAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of compound 4 (164 g), sodium cyanate (80 g) and manganese dioxide (500 g) in methanol (5.5 l) was stirred at room temperature. Ethanoic acid (122 g) was added dropwise and the resulting reaction mixture was stirred and refluxed overnight. The reaction mixture was filtered over dicalite, and the filter residue was rinsed with CH3OH/CH2Cl2. The filtrate was evaporated. The residue was partitioned between DCM and aqueous K2CO3 solution. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 152 g (87%) of methyl 6,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]-benzazepine-3-carboxylate (compound 6, mp. 179.3° C.).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. stirringwas stirred
  3. temperaturerefluxed overnight
  4. filtrationThe reaction mixture was filtered over dicalite
  5. washthe filter residue was rinsed with CH3OH/CH2Cl2
  6. customThe filtrate was evaporated
  7. customThe residue was partitioned between DCM and aqueous K2CO3 solution
  8. customThe organic layer was separated
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from ACN
  13. filtrationThe precipitate was filtered off
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3c088e2395bb498cb10787b0b9977b1d
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544979B1

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