Triethylamine → 1,3-dimethyl-6-{4-[3-{4-methanesulfonamido-2-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione hydrochloride

HRID 1085269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1085269
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=1)(=[O:4])=[O:3].[CH3:20][N:21]1[C:26]([N:27]2[CH2:32][CH2:31][N:30](CCCN(S(C)(=O)=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:29][CH2:28]2)=[CH:25][C:24](=[O:50])[N:23]([CH3:51])[C:22]1=[O:52].C(N(CC)CC)C>C(O)C>[ClH:16].[CH3:20][N:21]1[C:26]([N:27]2[CH2:32][CH2:31][N:30]([CH2:15][CH2:14][CH2:13][O:12][C:9]3[CH:10]=[CH:11][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][C:8]=3[N+:17]([O-:19])=[O:18])[CH2:29][CH2:28]2)=[CH:25][C:24](=[O:50])[N:23]([CH3:51])[C:22]1=[O:52]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 200611133-(4-Methanesulfonamido-2-nitrophenyloxy)propyl chlorideHCID 200613181,3-dimethyl-6-{4-[3-(N-methanesulfonyl-4-nitroanilino)propyl]piperazin-1yl}-2,4(1H,3H)-pyrimidinedione2×

Produkt 1

HCID 200612391,3-dimethyl-6-{4-[3-{4-methanesulfonamido-2-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione hydrochlorideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

0.31 g of 3-(4-methanesulfonamido-2-nitrophenyloxy)propyl chloride, 0.22 g of 1,3-dimethyl-6-(1-piperazinyl)-2,4(1H,3H)-pyrimidinedione (Compound 157) and 0.5 ml of triethylamine were dissolved under heat in 10 ml of ethanol to give a uniform solution. The solvent was distilled off under reduced pressure. After heating the residue at 110° C. for 2 hours, 10 ml of n-butanol were added and the resulting mixture was heated under stirring at 110° C. for 5 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in a dilute aqueous solution of sodium hydroxide. The thus-prepared solution was washed with chloroform. The water layer was then adjusted to pH 1-2 with dilute hydrochloric acid, washed with ethyl acetate, and then added with sodium hydrogencarbonate to raise the pH to 7-8. Precipitated insoluble matters were collected by filtration. The thus-collected substance was dried under reduced pressure and then dissolved in methanol. 15% HCl/methanol was added to convert it into the hydrochloride by a method known per se in the art, thereby obtaining 0.2 g of 1,3-dimethyl-6-{4-[3-{4-methanesulfonamido-2-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione hydrochloride (Compound 142 as crystals.

Aufarbeitung

  1. customto give a uniform solution
  2. distillationThe solvent was distilled off under reduced pressure
  3. addition10 ml of n-butanol were added
  4. temperaturethe resulting mixture was heated
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in a dilute aqueous solution of sodium hydroxide
  7. washThe thus-prepared solution was washed with chloroform
  8. washwashed with ethyl acetate
  9. additionadded with sodium hydrogencarbonate
  10. temperatureto raise the pH to 7-8
  11. filtrationPrecipitated insoluble matters were collected by filtration
  12. customThe thus-collected substance was dried under reduced pressure
  13. dissolutiondissolved in methanol
  14. addition15% HCl/methanol was added

Quellen und Nachweise

ORD-Eintrag
ord-46300991a2314b8dafa1036dcf9b3ab1
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008267

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