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4-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazoline → HCID 10229547, Verbindung

HRID 1241579
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1241579
C[Si](C)(C)N[Si](C)(C)C.[Na].[Br:11][C:12]1[C:17]([NH2:18])=[C:16]2[O:19][CH2:20][O:21][C:15]2=[CH:14][CH:13]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][N:24]=1>CN(C=O)C.O>[Br:11][C:12]1[C:17]([NH:18][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][N:24]=2)=[C:16]2[O:19][CH2:20][O:21][C:15]2=[CH:14][CH:13]=1
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Komponenten

6

Edukt 3

HCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazolineHCID 219360135-Bromo-1,3-benzodioxol-4-amineHCID 45051731Sodium hexamethyidisilazane

Produkt 1

HCID 10229547HCID 10229547, VerbindungAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

Sodium hexamethyldisilazane (1M solution in THF; 0.626 ml) was added to a solution of 6-bromo-2,3-methylenedioxyaniline (0.135 g) in DMF (2 ml) and the mixture was stirred at ambient temperature for 30 minutes. A solution of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (0.1 g) in DMF (3.5 ml) was added and the resultant mixture was stirred at ambient temperature for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (2×). The organic phase was washed with water and with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using an 80:17:3 mixture of methylene chloride, methanol and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.045 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.4 (m, 1H), 1.7 (m, 3H), 1.85 (m, 2H), 2.3 (m, 2H), 2.95 (m, 2H), 3.25 (m, 2H), 3.55 (m, 2H), 4.05 (s, 3H), 4.3 (m, 2H), 6.15 (s, 2H), 7.05 (d, 1H), 7.3 (d, 1H), 7.4 (s, 1H), 8.15 (s, 1H), 8.9 (s, 1H); Mass Spectrum: M+H+ 515 and 517; Elemental Analysis: Found C, 55.74; H, 5.30; N, 10.76. C24H27BrN4O4 requires C, 55.93; H, 5.28; N, 10.87%.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×)
  2. washThe organic phase was washed with water and with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. additionan 80:17:3 mixture of methylene chloride, methanol

Quellen und Nachweise

ORD-Eintrag
ord-bcd3a672062c4b1bba6be9d012aed963
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07115615B2

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