p-Toluenesulfonic acid → 3-(4-sec-butylphenyl)-2-(6-methoxypyridin-3-yl)quinazolin-4(3H)-one

HRID 1846336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846336
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:27][C:28]1[CH:46]=[CH:45][CH:44]=[CH:43][C:29]=1[C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]([CH2:41][CH3:42])[CH3:40])=[CH:35][CH:34]=1)=[O:31]>CC(N(C)C)=O>[CH:39]([C:36]1[CH:37]=[CH:38][C:33]([N:32]2[C:30](=[O:31])[C:29]3[C:28](=[CH:46][CH:45]=[CH:44][CH:43]=3)[N:27]=[C:9]2[C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:34][CH:35]=1)([CH2:41][CH3:42])[CH3:40]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 167700372-Amino-N-(4-sec-butylphenyl)benzamideHCID 23665763Sodium Bisulfite

Produkt 1

HCID 468414133-(4-sec-butylphenyl)-2-(6-methoxypyridin-3-yl)quinazolin-4(3H)-oneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

6-Methoxy-3-pyridinecarboxaldehyde (1.20 mmol), NaHSO3 (0.200 g, 1.90 mmol) and p-TsOH (0.024 g, 0.12 mmol) were added to a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (0.340 g, 1.20 mmol) in DMA (10 mL). The mixture was heated and stirred at 150° C. overnight and concentrated in vacuo. The residue was dissolved in EtOAc, and washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 15% to 100% EtOAc in heptane, afforded the title compound as a white solid (26%). 1H-NMR (300 MHz, DMSO-d6): δ 8.11-8.27 (m, 2H), 7.89-7.91 (m, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.51-7.67 (m, 2H), 7.11-7.33 (m, 4H), 6.62 (d, J=8.0 Hz, 1H), 3.77 (s, 3H), 2.54-2.68 (m, 1H), 1.30-1.71 (m, 2H), 1.16 (d, J=7.0 Hz, 3H), 0.64 (t, J=7.4 Hz, 3H). MS (APCI) m/z: 386 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialbrine, dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 15% to 100% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-59d627152e774058b7abf294dba2b145
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952021B2

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