2-Chloro-6,7-dimethoxy-4-quinazolinamine → Doxazosin

HRID 428378

Reaktionsgleichung

Reaktionsgleichung von HRID 428378
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[O:17]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][CH2:19][CH:18]1[C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28]>C(O)CCC>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:2]([NH2:1])=[N:3][C:4]([N:32]3[CH2:33][CH2:34][N:29]([C:27]([CH:18]4[O:17][C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[O:20][CH2:19]4)=[O:28])[CH2:30][CH2:31]3)=[N:5][C:6]2=[CH:7][C:8]=1[O:14][CH3:15]

Komponenten

4

Edukt 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 2735449N-1,4-Benzodioxane-2-carbonyl piperazine

Produkt 1

HCID 3157DoxazosinAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

4-amino-2-chloro-6,7-dimethoxyquinazoline (3.2 g, 13.35 mmol) and compound 1 (3.4 g, 13.75 mmol) prepared from Example 3 were dissolved in 72 mL of n-butanol. The mixture was refluxed under nitrogen for 3.5 hours. After cooling to 75° C., the solid product was obtained by filtration and dried to afford 5.25 g of hydrochloride salt of Doxazosin (10.76 mmol, 81% yield). 1 N NaOH solution was added to the salt. The mixture was heated to help the salt dissolved. After cooling, the mixture was extracted with 150 mL of dichloromethane twice. The organic layer was dried with anhydrous sodium sulfate and concentrated to afford 4.61 g of Doxazosin.

Aufarbeitung

  1. temperatureThe mixture was refluxed under nitrogen for 3.5 hours
  2. customthe solid product was obtained by filtration
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c0da6d462a2a4f0eb506784a32c61fdd
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313294B1

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