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Diethyl Ether → 4-Amino-6-benzyloxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline

HRID 2228490
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2228490
Cl.[N:2]1([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:36][CH3:37])=[C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=2)[N:21]=[C:20](Cl)[N:19]=1.C(N(CC)CC)C.C(OCC)C>C(O)CCC>[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:36][CH3:37])=[C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=2)[N:21]=[C:20]([N:13]2[CH2:14][CH2:15][CH2:16][N:10]([C:8]([N:2]3[CH2:3][CH2:4][O:5][CH2:6][CH2:7]3)=[O:9])[CH2:11][CH2:12]2)[N:19]=1
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Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 109799944-Amino-6-benzyloxy-2-chloro-7-methoxyquinazolineHCID 227070621-(4-Morpholinecarbonyl)-1,4-diazepane hydrochloride

Produkt 1

HCID 109620274-Amino-6-benzyloxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazolineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

1-(4-Morpholinecarbonyl)-1,4-diazepane hydrochloride (16 g, 0.075 mol) and 4-amino-6-benzyloxy-2-chloro-7-methoxyquinazoline (15 g, 0.048 mol) were added to a solution of triethylamine (20 ml, 0.144 mol) in n-butanol (200 ml) and the reaction stirred at reflux for 1 hour. On cooling, the mixture was concentrated under reduced pressure and the residue partitioned between dichloromethane (400 ml) and water (400 ml). The phases were separated and the organic layer dried (MgSO4), filtered and evaporated under reduced pressure to give a cream coloured solid. Trituration with diethyl ether gave the title compound as a solid (16.35 g, 70%). Rf 0.50 (0.880 aqueous ammonia:methanol:dichloromethane 1:7:92, v/v). MS m/z 493 (MH)+. 1H-NMR (CDCl3): Γ=2.03 (2H, m), 3.18 (4H, m), 3.34 (2H, t), 3.56 (2H, m), 3.65 (5H, m), 3.85 (2H, m), 4.00 (4H, m), 5.00 (1H, bs), 5.18 (2H, s), 6.87 (1H, bs), 7.37 (4H, m), 7.47 (3H, m).

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. temperatureOn cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between dichloromethane (400 ml) and water (400 ml)
  5. customThe phases were separated
  6. dry with materialthe organic layer dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give a cream

Quellen und Nachweise

ORD-Eintrag
ord-25ff5d78c0c14b2890ed948050a6b610
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06417194B1

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