p-Toluenesulfonic acid → 5,7-dimethoxy-2-(4-(morpholinomethyl)phenyl)quinazolin-4(3H)-one

HRID 1498705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1498705
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[N:15]1([CH2:21][C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CN(C)C(=O)C.O>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:26]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:29][CH:28]=1)=[N:1]2

Komponenten

8

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 27954984-[(Morpholin-4-yl)methyl]benzaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

Produkt 1

HCID 1360380055,7-dimethoxy-2-(4-(morpholinomethyl)phenyl)quinazolin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 2-amino-4,6-dimethoxy-benzamide (150 mg, 0.76 mmol) and 4-morpholin-4-ylmethyl benzaldehyde (156 mg, 0.76 mmol) in N,N-dimethyl acetamide (10 mL), NaHSO3 (150 mg, 0.84 mmol) and p-TSA (174 mg, 0.91 mmol) were added and the reaction mixture was heated at 150° C. for 5 h. The reaction mixture was cooled to room temperature, water was added and the mixture was neutralized with NaHCO3. The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography to give 5,7-dimethoxy-2-(4-(morpholinomethyl)phenyl)quinazolin-4(3H)-one, which was converted to the hydrochloride salt (165 mg, 51%). Selected data: MS (ES) m/z: 382.07; MP 206-208° C. (at decomposition).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customto give the crude product, which
  4. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-32219b2121b347debe53a41b0ad6e90f
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199990B2

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