Acetic Anhydride → HCID 59551680, Verbindung

HRID 1170241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1170241
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH:32]4[CH2:35][NH:34][CH2:33]4)=[CH:28][CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>C(Cl)Cl>[C:8]([O:12][C:13]([N:15]1[CH2:16][CH2:17][CH:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH:32]4[CH2:33][N:34]([C:1](=[O:3])[CH3:2])[CH2:35]4)=[CH:28][CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH2:19][CH2:20]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 595517494-[7-(Azetidin-3-yloxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 59551680HCID 59551680, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Acetic anhydride (66 μL, 703 μmol) was added dropwise with stirring at rt to a mixture of 4-[7-(Azetidin-3-yloxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester (180 mg, 469 μmol), as prepared in the previous step, in DCM (1.0 mL). The resulting homogeneous yellow solution was stirred overnight, and was then partitioned with DCM (3 mL) and IM NaHCO3 (1×4 mL). The organic layer was dried (Na2SO4), concentrated, and purified by silica flash chromatography (8:2 DCM/acetone/3% DMEA eluent) to afford the title compound as a white crystalline film (88.3 mg, 44% over two steps). LC/MS (ESI): calcd mass 426.2, found 426.9 (MH)+.

Aufarbeitung

  1. customwas then partitioned with DCM (3 mL) and IM NaHCO3 (1×4 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by silica flash chromatography (8:2 DCM/acetone/3% DMEA eluent)

Quellen und Nachweise

ORD-Eintrag
ord-138a22dc3722474eb18ae6fc27f602a6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825244B2

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