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Potassium Acetate → HCID 178518457, Verbindung

HRID 706015
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 706015
OS(C(F)(F)F)(=O)=O.[C:9](=[NH:32])([O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)=[CH:16][CH:15]=1)[NH2:10].[OH:33]/[CH:34]=[C:35](/[CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[N:45][CH:46]=1)\[C:36](OC)=O.C([O-])(=O)C.[K+]>C1(C)C=CC=CC=1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][O:11][C:9]3[NH:10][CH:36]=[C:35]([CH2:40][C:41]4[CH:46]=[N:45][CH:44]=[N:43][CH:42]=4)[C:34](=[O:33])[N:32]=3)=[CH:19][CH:18]=2)=[CH:22][C:23]=1[C:28]([F:31])([F:30])[F:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 517044Potassium AcetateHCID 67774726(Z)-methyl 3-hydroxy-2-(pyrimidin-5-ylmethyl)acrylateHCID 866661912-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate triflate

Produkt 1

HCID 178518457HCID 178518457, VerbindungAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

An alternative synthesis was provided to prepare the compound of Example 20. A suspension of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate triflate (17.29 g, 34.0 mmol), methyl (2Z)-3-hydroxy-2-(5-pyrimidinylmethyl)-2-propenoate (5.5 g, 28.3 mmol) and potassium acetate (5.56 g, 56.6 mmol) in toluene (200 mL) was stirred at room temperature for 2 min. and then heated to reflux for 3 h. The mixture was filtered off and concentrated to dryness, which was then dissolved in DMF and purified by MDAP with TFA. The purified fractions were combined and neutrallized with ammonia. The organic solvent was removed under vacuo and the water layer was extracted with EA. The organic layer was combined and dried over Na2SO4 which was concentrated to give the white solid. The solid was recrystallized in MeCN to afford the title compound (3.0 g, 21.06% yield) LCMS: rt=3.43 min, [M+H+]=503.

Aufarbeitung

  1. customAn alternative synthesis
  2. customwas provided
  3. temperatureheated
  4. temperatureto reflux for 3 h
  5. filtrationThe mixture was filtered off
  6. concentrationconcentrated to dryness, which
  7. dissolutionwas then dissolved in DMF
  8. custompurified by MDAP with TFA
  9. customThe organic solvent was removed under vacuo
  10. extractionthe water layer was extracted with EA
  11. dry with materialdried over Na2SO4 which
  12. concentrationwas concentrated
  13. customto give the white solid
  14. customThe solid was recrystallized in MeCN

Quellen und Nachweise

ORD-Eintrag
ord-fefd44536bc24cfb938ee53f240923c3
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09174968B2

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