p-Toluenesulfonic acid → HCID 136037978, Verbindung

HRID 1498696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1498696
[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].[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=2)[CH2:18][CH2:17]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:27]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:19]3[CH2:18][CH2:17][N:16]([CH3:15])[CH2:21][CH2:20]3)=[CH:30][CH:29]=1)=[N:1]2

Komponenten

8

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 71646514-[(4-Methylpiperazin-1-yl)methyl]benzaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

Produkt 1

HCID 136037978HCID 136037978, Verbindung

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-(4-methyl piperazin-1-ylmethyl)benzaldehyde (166 mg, 0.76 mmol) in N,N-dimethyl acetamide (10 mL), NaHSO3 (149 mg, 0.84 mmol) and p-TSA (319 mg, 1.68 mmol) were added and the reaction mixture was heated at 150° C. for 3 h. The mixture was cooled to room temperature and water was added and neutralized by addition of NaHCO3. The solvent was removed under reduced pressure to give the crude product. The crude was purified by column chromatography (silica gel 230-400 mesh; 4% NH3 in methanol/CH2Cl2 as eluent) to give the product 5,7-dimethoxy-2-(4-((4-methylpiperazin-1-yl)methyl)phenyl)quinazolin-4(3H)-one as a free base, which was converted to the hydrochloride salt (115 mg, 35%). Selected data: MS (ES) m/z: 395.2; MP 275-277° C. (hydrochloride).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customto give the crude product
  4. customThe crude was purified by column chromatography (silica gel 230-400 mesh; 4% NH3 in methanol/CH2Cl2 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-6ee38becfdef41dbb25f96804a2bf0a0
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199990B2

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