Water → 2-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile

HRID 508181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508181
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=2)=[CH:10][CH:9]=1.[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][OH:39])=[CH:32][CH:31]=2)[C:25]([C:40]#[N:41])=[C:24](SC2C=CC=CC=2)[N:23]=1.O>COCCOC.C(O)(=O)C>[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][OH:39])=[CH:34][CH:35]=2)[C:25]([C:40]#[N:41])=[C:24]([O:20][CH2:19][C:17]2[N:18]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=3)[O:15][CH:16]=2)[N:23]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 15555159HCID 15555159, VerbindungHCID 23665647Potassium tert-butoxideHCID 666304992-Amino-4-[4-(2-hydroxyethoxy)phenyl]-6-phenylthiopyridine-3,5-dicarbonitrile

Produkt 1

HCID 666721372-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

72 mg (0.64 mmol) of potassium tert-butoxide are suspended in 1 ml of dry 1,2-dimethoxyethane. In succession, 270 mg (1.29 mmol) of the compound from Example 100A and 50 mg (0.13 mmol) of the compound from Example 99A are then added. The reaction mixture is stirred at 60° C. for 2 h and then cooled to RT and stirred at this temperature for a further 8 h. 5 ml of water and 1 ml of 2 N acetic acid are then added to the mixture. A precipitate is formed, which is filtered off with suction and purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gives the product as a yellow solid.

Aufarbeitung

  1. temperaturecooled to RT
  2. stirringstirred at this temperature for a further 8 h
  3. customA precipitate is formed
  4. filtrationwhich is filtered off with suction
  5. custompurified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  6. customRemoval of the solvent
  7. customon a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-6665616947464c6a900b31c5405d90c3
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09095582B2

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