Acetic Acid → Erlotinib Hydrochloride

HRID 238998

Reaktionsgleichung

Reaktionsgleichung von HRID 238998
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([C:29]#[CH:30])[CH:26]=[CH:27][CH:28]=1.C(O)(=O)C>C(#N)C>[CH3:16][O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:2]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[CH:30])[CH:24]=3)=[N:3][CH:4]=[N:5][C:6]2=[CH:7][C:8]=1[O:17][CH2:18][CH2:19][O:20][CH3:21].[ClH:1]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 104682Benzenamine, 3-ethynyl-HCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

Produkt 1

HCID 176871Erlotinib Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

50 g of 4-chloro-6,7-bis(2-methoxyethoxy) quinazoline was suspended in 1500 ml acetonitrile and 46 g of 3-aminophenyl acetylene was added at 25-30° C., followed by 10 ml acetic acid. The reaction mass was stirred at 25-30° C. for 30 minutes. Solid obtained was filtered, washed with water and dried under vacuum. This solid was suspended in water, basified with potassium hydroxide and stirred for 10 minutes. The resulting erlotinib base was isolated, washed with acetonitrile and dried under vacuum. The solid obtained was then suspended in water and acidified to pH 1.0-2.0 using hydrochloric acid. The reaction mixture was stirred for 2 hours, filtered, washed with water and dried at 40-45° C. to obtain 63 g of erlotinib hydrochloride.

Aufarbeitung

  1. customSolid obtained
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under vacuum
  5. stirringstirred for 10 minutes

Quellen und Nachweise

ORD-Eintrag
ord-104de0332f164e28ac2ab9cfac85625f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642758B2

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