Hydrochloric Acid → Vandetanib hydrochloride

HRID 238090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238090
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Br:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[C:26]([F:31])[CH:25]=1.Cl>C(O)(C)C>[ClH:1].[Br:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[C:26]([F:31])[CH:25]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1230504-Bromo-2-fluoroanilineHCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline

Produkt 1

HCID 23133323Vandetanib hydrochlorideAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

A suspension of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (200 mg, 0.62 mmol) and 4-bromo-2-fluoroaniline (142 mg, 0.74 mmol) in isopropanol (3 ml) containing 6N hydrogen chloride in isopropanol (110 μl, 0.68 ml) was heated at reflux for 1.5 hours. After cooling, the precipitate was collected by filtration, washed with isopropanol followed by ether and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride (304 mg, 90%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with isopropanol
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-066711626caf41f08c53419fad28759d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642608B2

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