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Formamidine acetate → 6-Methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4(3H)-one

HRID 238095
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238095
[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][C:5]([O:13][CH3:14])=[C:4]([O:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)[CH:3]=1.C(O)(=O)C.[CH:28](N)=[NH:29]>COCCO>[CH3:14][O:13][C:5]1[CH:6]=[C:7]2[C:2](=[CH:3][C:4]=1[O:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]1)[N:1]=[CH:28][NH:29][C:8]2=[O:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 160693Formamidine acetate2×HCID 21874813Ethyl 2-amino-5-methoxy-4-((1-methylpiperidin-4-yl)methoxy)benzoate

Produkt 1

HCID 1354703756-Methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4(3H)-oneAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A solution of ethyl 6-amino-3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (16.1 g, 50 mmol) in 2-methoxyethanol (160 ml) containing formamidine acetate (5.2 g, 50 mmol) was heated at 115° C. for 2 hours. Formamidine acetate (10.4 g, 100 mmol) was added in portions every 30 minutes over 4 hours. Heating was prolonged for 30 minutes after the last addition. After cooling, the volatiles were removed under vacuum. The solid was dissolved in ethanol (100 ml) and methylene chloride (50 ml). The precipitate was removed by filtration and the filtrate was concentrated to a final volume of 100 ml. The suspension was cooled to 5° C. and the solid was collected by filtration, washed with cold ethanol followed by ether and dried under vacuum overnight at 60° C. to give 6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)-3,4-dihydroquinazolin-4-one (12.7 g, 70%).

Aufarbeitung

  1. temperatureHeating
  2. additionafter the last addition
  3. temperatureAfter cooling
  4. customthe volatiles were removed under vacuum
  5. dissolutionThe solid was dissolved in ethanol (100 ml)
  6. customThe precipitate was removed by filtration
  7. concentrationthe filtrate was concentrated to a final volume of 100 ml
  8. temperatureThe suspension was cooled to 5° C.
  9. filtrationthe solid was collected by filtration
  10. washwashed with cold ethanol
  11. customdried under vacuum overnight at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-d094b5ec3c4f4511ab7b1280f2482a27
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642608B2

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