Pyridine → HCID 76584760, Verbindung

HRID 911367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911367
Cl.[NH2:2][OH:3].N1C=CC=CC=1.[C:10]([C:13]1[CH:38]=[CH:37][C:16]([CH2:17][NH:18][C:19]2[C:29]3[CH2:28][CH2:27][N:26]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])[CH2:25][CH2:24][C:23]=3[CH:22]=[CH:21][C:20]=2[Cl:36])=[CH:15][CH:14]=1)(=O)[CH3:11]>C(O)C>[Cl:36][C:20]1[CH:21]=[CH:22][C:23]2[CH2:24][CH2:25][N:26]([C:30](=[O:35])[C:31]([F:34])([F:32])[F:33])[CH2:27][CH2:28][C:29]=2[C:19]=1[NH:18][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([C:10](=[N:2][OH:3])[CH3:11])=[CH:38][CH:37]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 59828832HCID 59828832, Verbindung

Produkt 1

HCID 76584760HCID 76584760, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Add hydroxylamine hydrochloride (19 mg, 0.27 mmol) and pyridine (0.04 mL, 0.54 mmol) to a solution of 6-(4-acetylbenzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (115 mg, 0.27 mmol) in ethanol (10 mL). Heat the mixture to reflux for 2 h. Remove the solvent in vacuo and partition the residue between DCM and 0.1N aqueous HCl. Dry the organic phase over Na2SO4, filter and concentrate. Dissolve the oil into the minimum amount of ether and add hexane to precipitate the solid. Filter to obtain 7-chloro-6-[4-(1-hydroxyiminoethyl)-benzylamino]3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a solid (12 mg, 94%) that was used without further purification. MS (ES+) m/z: 440 (M+H)+.

Aufarbeitung

  1. temperatureHeat the mixture
  2. temperatureto reflux for 2 h
  3. customRemove the solvent in vacuo
  4. custompartition the residue between DCM and 0.1N aqueous HCl
  5. dry with materialDry the organic phase over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. dissolutionDissolve the oil into the minimum amount of ether
  9. additionadd hexane
  10. customto precipitate the solid
  11. filtrationFilter

Quellen und Nachweise

ORD-Eintrag
ord-e83761b1d4ff41efa04a209245f70e9f
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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