Triethylamine → 2-[4-(4-Isopropylcinnamoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxyquinazolin

HRID 1449159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449159
[CH:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.Cl.[N:29]1([C:35]2[N:44]=[C:43]([NH2:45])[C:42]3[C:37](=[CH:38][C:39]([O:48][CH3:49])=[C:40]([O:46][CH3:47])[CH:41]=3)[N:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CC(C)=O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([N:32]2[CH2:33][CH2:34][N:29]([C:35]3[N:44]=[C:43]([NH2:45])[C:42]4[C:37](=[CH:38][C:39]([O:48][CH3:49])=[C:40]([O:46][CH3:47])[CH:41]=4)[N:36]=3)[CH2:30][CH2:31]2)=[O:12])=[CH:13][CH:14]=1)([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 728543-(4-(1-Methylethyl)phenyl)-2-propenoic acidHCID 204738332-Piperazine-4-amino-6,7-dimethoxy quinoline hydrochloride

Produkt 1

HCID 544068222-[4-(4-Isopropylcinnamoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxyquinazolin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of 342 mg. of 4-isopropylcinnamic acid and 727 mg. of triethylamine in 20 ml. of acetone were added dropwise under ice-cooling 195 mg. of ethyl chlorocarbonate and the resulting mixture was stirred for 3.5 hours. Then, 543 mg. of 2-(piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline.hydrochloride were added thereto and stirring was continued at room temperature overnight. Then, the acetone was distilled off, the residue was dissolved in 20 ml. of 10% K2CO3 and extracted with ethyl acetate. After drying over magnesium sulfate, the extract was concentrated and recrystallization from methanol gave 361 mg. of the desired product.

Aufarbeitung

  1. additionTo a mixture of 342 mg
  2. temperaturecooling 195 mg
  3. distillationThen, the acetone was distilled off
  4. dissolutionthe residue was dissolved in 20 ml
  5. extractionof 10% K2CO3 and extracted with ethyl acetate
  6. dry with materialAfter drying over magnesium sulfate
  7. concentrationthe extract was concentrated
  8. customrecrystallization from methanol
  9. customgave 361 mg

Quellen und Nachweise

ORD-Eintrag
ord-11cb611237c5439e89410348931acdb0
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04189484

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