Ethyl chloroformate → 6-chloro-3,4-dihydro-2-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride

HRID 329725

Reaktionsgleichung

Reaktionsgleichung von HRID 329725
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.C(Cl)(=O)OCC.[NH2:23][CH:24]1[CH2:30][CH:29]2[N:31]([CH3:32])[CH:26]([CH2:27][CH2:28]2)[CH2:25]1.C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH:23][CH:24]2[CH2:25][CH:26]3[N:31]([CH3:32])[CH:29]([CH2:28][CH2:27]3)[CH2:30]2)=[O:16])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1

Komponenten

9

Edukt 4

HCID 10928Ethyl chloroformateHCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 516892Sodium BicarbonateHCID 145172316-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid

Produkt 1

HCID 198711806-chloro-3,4-dihydro-2-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4.8 g of 6-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 100 ml of tetrahydrofuran and 10 ml of dimethylformamide is cooled to below 0° C. and 5 ml of triethylamine is added under stirring thereto. Further, 2.5 g of ethyl chlorocarbonate is added and the mixture is stirred at room temperature for 45 minutes. To the resultant mixture is added 3.0 g of 3-amino-8-methyl-8-azabicyclo[3.2.1]octane and the mixture stirred for 4 hours. After completion of the reaction, aqueous sodium hydrogen carbonate and ethyl acetate are added. The organic layer is separated, washed with water and dried over magnesium sulfate. The solvent is distilled off and the residue is converted into the corresponding hydrochloride by treating with ethanolic hydrochloric acid followed by recrystallizing from ethanol-water to give 6-chloro-3,4-dihydro-2-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 325°-328° C. with decomposition.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 45 minutes
  2. stirringthe mixture stirred for 4 hours
  3. additionare added
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. additionby treating with ethanolic hydrochloric acid
  9. customby recrystallizing from ethanol-water

Quellen und Nachweise

ORD-Eintrag
ord-32846653c30a4e1d8c2187d6ee8d761c
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892872

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