Amantadine → 4-(1-Adamantylamino)-2-chloro-6-nitroquinazoline

HRID 1250602

Reaktionsgleichung

Reaktionsgleichung von HRID 1250602
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O.C(N(C(C)C)C=O)(C)C.[C:30]12([NH2:40])[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2.C(N(CC)CC)C>O>[C:30]12([NH:40][C:7]3[C:6]4[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[N:10]=[C:9]([Cl:18])[N:8]=3)[CH2:37][CH:36]3[CH2:35][CH:34]([CH2:33][CH:32]([CH2:38]3)[CH2:31]1)[CH2:39]2

Komponenten

7

Edukt 5

HCID 2130AmantadineHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 75912N,N-bis(1-methylethyl)formamideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Produkt 1

HCID 183264334-(1-Adamantylamino)-2-chloro-6-nitroquinazolineAusbeute 20,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 250 mg (1.21 mmol) of 6-nitroquinazoline-2,4(1H,3H)-dione were added 5.00 ml (53.64 mmol) of phosphorus oxychloride and 0.18 ml (1.21 mmol) of diisopropylformamide, and the resulting mixture was subjected to heating under reflux for 24 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 5 ml of acetonitrile, followed by addition of 183 mg (1.21 mmol) of 1-adamantylamine and 0.84 ml (6.05 mmol) of triethylamine under ice cooling and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 90 mg (20.7%) of the title compound.

Aufarbeitung

  1. temperatureto heating
  2. temperatureunder reflux for 24 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 5 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-f77c119c947f45b7bbc8fb01093600d6
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

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