Potassium Carbonate → 4-[4-bromo-2-(trifluoromethyl)phenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 2405357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405357
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][C@@H:15]2[CH2:19][CH2:18][N:17]([C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:16]2)=[O:10])=[C:4]([C:26]([F:29])([F:28])[F:27])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH2:14][C@@H:15]3[CH2:19][CH2:18][N:17]([C:20]([CH:22]4[CH2:24][CH2:23]4)=[O:21])[CH2:16]3)=[N:12][NH:11][C:9]2=[O:10])=[C:4]([C:26]([F:29])([F:28])[F:27])[CH:3]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 71087502N-[4-bromo-2-(trifluoromethyl)phenyl]-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide

Produkt 1

HCID 673538084-[4-bromo-2-(trifluoromethyl)phenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-oneAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a round bottom flask were added N-[4-bromo-2-(trifluoromethyl)phenyl]-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide (1025 mg, 2.148 mmol) and potassium carbonate (1203 mg, 8.70 mmol). The mixture was suspended in water (100 mL) and refluxed for 16 h at 115° C. Analysis by LCMS indicated consumption of starting material and formation of desired product and by-products related to the starting material. The solution was neutralized to pH=7 with 1N aq HCl and diluted with 150 mL of ethyl acetate. The aqueous phase was extracted with ethyl acetate (3×) and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. This material was purified by silica gel chromatography (0-20% isopropanol/ethyl acetate), to afford the title product (177 mg, 18%). MS(ES)+ m/e 459.2, 461.2 M+H]+.

Aufarbeitung

  1. customconsumption of starting material and formation of desired product and by-products
  2. additiondiluted with 150 mL of ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThis material was purified by silica gel chromatography (0-20% isopropanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-12084132df694d4992bc2232da1770d6
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802864B2

Notizen zur Reaktion

Wird geladen…