Hydrochloric Acid → 3-[1-(6-Ethoxy-7-hydroxy-2-morpholino-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline

HRID 617157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617157
[H-].[Na+].C1(S)C=CC=CC=1.Cl.[CH2:11]([O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24]CC)[N:20]=[C:19]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:18]=[C:17]2[N:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:48](=[O:49])[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([CH3:50])[CH:46]=3)[N:41]([CH3:51])[C:40]2=[O:52])[CH2:35][CH2:34]1)[CH3:12].Cl>CN(C=O)C.O>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[OH:24])[N:20]=[C:19]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:18]=[C:17]2[N:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:48](=[O:49])[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([CH3:50])[CH:46]=3)[N:41]([CH3:51])[C:40]2=[O:52])[CH2:35][CH2:34]1)[CH3:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 99388233-[1-(6,7-Diethoxy-2-morpholino-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline hydrochloride

Produkt 1

HCID 1358228343-[1-(6-Ethoxy-7-hydroxy-2-morpholino-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazolineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

In 10 ml of DMF was suspended 1.19 g (30.0 mmol) of 60% sodium hydride, and 3.07 ml (30.0 mmol) of thiophenol in 20 ml of DMF was dropwised under ice-cooling. After the mixture was stirred at ice-cooling for 10 minutes, 5.74 g (10.0 mmol) of Compound 10 obtained in Example 10 in DMF (50 ml) was added at ice-cooling, then the reaction mixture was stirred at 150° C. for 20 hours. After the reaction mixture was cooled to room temperature, water was added, pH of the reaction mixture was adjusted at 5 by concentrated hydrochloric acid and was subjected to extraction with chloroform. The organic layer was washed with sodium chloride solution and dried, concentrated to give residue which was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1). The more polar product obtained was recrystallized from ethanol/ether to give 2.67 g (yield: 49%) of Compound 47 as white crystals.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling for 10 minutes
  3. temperaturecooling
  4. stirringthe reaction mixture was stirred at 150° C. for 20 hours
  5. extractionwas subjected to extraction with chloroform
  6. washThe organic layer was washed with sodium chloride solution
  7. customdried
  8. concentrationconcentrated
  9. customto give residue which
  10. customwas purified by silica gel column chromatography (eluent: chloroform/methanol=50/1)
  11. customThe more polar product obtained
  12. customwas recrystallized from ethanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-5199e45a13c646aeb680c0b3843f27de
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948784

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