Benzoic Acid → Erlotinib Hydrochloride

HRID 238996

Reaktionsgleichung

Reaktionsgleichung von HRID 238996
[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)C1C=CC=CC=1>CO>[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 243Benzoic AcidHCID 104682Benzenamine, 3-ethynyl-HCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

Produkt 1

HCID 176871Erlotinib Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

10.0 g of 4-chloro-6,7-bis(2-methoxyethoxy) quinazoline was suspended in 300 ml methanol and 9.2 g of 3-aminophenyl acetylene was charged at 25-30° C. Further 2.0 ml of benzoic acid was added. The reaction mass was stirred at 25-30° C. for 4 hours. Solid obtained was filtered, washed with methanol and dried under vacuum. This solid was suspended in water and then basified with sodium hydroxide and stirred for 10 minutes. The resulting erlotinib base was isolated, washed with water and dried under vacuum. The base was 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 to obtain 11.2 g of erlotinib hydrochloride.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9143f54b1f31480fb8373d23a78b6dc4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642758B2

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