Methanesulfonic Acid → Erlotinib Hydrochloride

HRID 238995

Reaktionsgleichung

Reaktionsgleichung von HRID 238995
[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.CS(O)(=O)=O>>[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

4

Edukt 3

HCID 6395Methanesulfonic AcidHCID 104682Benzenamine, 3-ethynyl-HCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

Produkt 1

HCID 176871Erlotinib Hydrochloride

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

5 g of 4-chloro-6,7-bis(2-methoxyethoxy) quinazoline was suspended in 150 ml denatured spirit (SPDS) and 4.6 g of 3-aminophenyl acetylene was charged at 25-30° C. Further 1.0 ml of methane sulphonic acid was added. The reaction mass was stirred at 25-30° C. for 3 hours. Solid obtained was filtered, washed with SPDS and dried under vacuum. This solid was suspended in water, basified with ammonia 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 at 40-45° C. to obtain 5.8 g of erlotinib hydrochloride.

Aufarbeitung

  1. additionwas charged at 25-30° C
  2. customSolid obtained
  3. filtrationwas filtered
  4. washwashed with SPDS
  5. customdried under vacuum
  6. stirringstirred for 10 minutes

Quellen und Nachweise

ORD-Eintrag
ord-84b9bfb18bbe48c0987fa54d56495d84
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642758B2

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