Potassium Iodide → 4-(3-Acetoxy-4-methylanilino)-6-methoxy-7-((1-methylbenzimidazol-2-yl)methoxy)quinazoline

HRID 1384582

Reaktionsgleichung

Reaktionsgleichung von HRID 1384582
Cl.[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([OH:22])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)(=[O:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:36][C:37]1[N:41]([CH3:42])[C:40]2[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=2[N:38]=1>CN(C=O)C>[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:36][C:37]3[N:41]([CH3:42])[C:40]4[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=4[N:38]=3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)(=[O:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 2480442-(Chloromethyl)-1-methylbenzimidazole2×HCID 1356711804-(3-Acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride

Produkt 1

HCID 226249724-(3-Acetoxy-4-methylanilino)-6-methoxy-7-((1-methylbenzimidazol-2-yl)methoxy)quinazolineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 4-(3-acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (240 mg, 0.64 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (310 mg, 2.25 mmol), potassium iodide (10 mg, 0.064 mmol) and 2-chloromethyl-1-methylbenzimidazole (153 mg, 0.7 mmol) in DMF (12 ml) was heated at 65° C. for 3 hours. Further 2-chloromethyl-1-methylbenzimidazole (90 mg, 0.41 mmol) and potassium carbonate (165 mg, 1.2 mmol) were added and heating continued for 2 hours. The solvent was removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with water and the solid product collected by filtration, washed with ether and dried under vacuum to give 4-(3-acetoxy-4-methylanilino)-6-methoxy-7-((1-methylbenzoimidazol-2-yl)methoxy)quinazoline (292 mg, 95%). MS-ESI: 506 [MNa]+

Aufarbeitung

  1. custom(prepared
  2. temperatureheating
  3. customThe solvent was removed by evaporation
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was triturated with water
  10. filtrationthe solid product collected by filtration
  11. washwashed with ether
  12. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7974f7647296438298fdacb22346fb68
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258951B1

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