Ammonia → 4-(6-Chloro-2,3-methylenedioxyanilino)-7-ethoxy-5-(1-methylpiperidin-4-yloxy)quinazoline

HRID 1826321

Reaktionsgleichung

Reaktionsgleichung von HRID 1826321
N(C(OC(C)(C)C)=O)=NC(O[C:6](C)(C)[CH3:7])=O.[Cl:17][C:18]1[C:23]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([OH:43])=[CH:32][C:33]=3[O:35][CH:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)[N:28]=[CH:27][N:26]=2)=[C:22]2[O:44][CH2:45][O:46][C:21]2=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.N>C(Cl)Cl.C(OCC)C.C(O)C>[Cl:17][C:18]1[C:23]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:43][CH2:6][CH3:7])=[CH:32][C:33]=3[O:35][CH:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)[N:28]=[CH:27][N:26]=2)=[C:22]2[O:44][CH2:45][O:46][C:21]2=[CH:20][CH:19]=1

Komponenten

9

Edukt 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 1355107014-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-5-(N-methylpiperidin-4-yloxy)quinazoline

Produkt 1

HCID 685792644-(6-Chloro-2,3-methylenedioxyanilino)-7-ethoxy-5-(1-methylpiperidin-4-yloxy)quinazolineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of di-tert-butyl azodicarboxylate (0.26 g) in methylene chloride (1 ml) was added dropwise to a stirred mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-5-(N-methylpiperidin-4-yloxy)quinazoline (0.12 g), ethanol (0.019 g), triphenylphosphine (0.15 g) and methylene chloride (2 ml) and the resultant mixture was stirred at ambient temperature for 1 hour. A 2M solution of hydrogen chloride in diethyl ether (3 ml) was added and the mixture was stirred at ambient temperature for 1.5 hours. Diethyl ether (1 ml) was added and the precipitate was isolated and dried under vacuum. The solid so obtained was dissolved in a 9:1 mixture of methylene chloride and a saturated methanolic ammonia solution. The mixture was filtered and the filtrate was evaporated. The residue was triturated under pentane and the resultant solid was isolated and dried under vacuum. There was thus obtained the title compound (0.092 g); NMR Spectrum: (CDCl3) 1.5 (t, 3H), 1.95–2.1 (m, 2H), 2.15–2.5 (m, 2H), 2.3 (s, 3H), 2.3–2.4 (m, 2H), 2.7 (br s, 2H), 4.15 (m, 2H), 4.6 (m, 1H), 6.05 (s, 2H), 6.5 (d, 1H), 6.7 (d, 1H), 6.8 (d, 1H), 6.95 (d, 1H), 8.5 (s, 1H), 9.25 (br s, 1H); Mass Spectrum: M+H+ 457 and 459.

Aufarbeitung

  1. customthe precipitate was isolated
  2. customdried under vacuum
  3. customThe solid so obtained
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated
  6. customThe residue was triturated under pentane
  7. customthe resultant solid was isolated
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8522204037164e3e9bc92909beb05c9f
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049438B2

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