Water → methyl N-[[2-chloro-5-[1-[3-(1-methylethyl)-1,2,4-thiadiazol-5-yl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate

HRID 70243

Reaktionsgleichung

Reaktionsgleichung von HRID 70243
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17].Cl[C:20]1[S:24][N:23]=[C:22]([CH:25]([CH3:27])[CH3:26])[N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:20]3[S:24][N:23]=[C:22]([CH:25]([CH3:27])[CH3:26])[N:21]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 128746835-Chloro-3-(propan-2-yl)-1,2,4-thiadiazole2×HCID 178502067HCID 178502067, Verbindung

Produkt 1

HCID 66790093methyl N-[[2-chloro-5-[1-[3-(1-methylethyl)-1,2,4-thiadiazol-5-yl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

A mixture of methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. the product of Step B, Example 4) (0.02 g, 0.75 mmol), 5-chloro-3-(1-methylethyl)-1,2,4-thiadiazole (i.e. the product of Step A) (0.61 g, 3.75 mmol) and potassium carbonate (0.25 g, 1.5 mmol) in N-methyl-2-pyrrolidinone (2.5 mL) was heated in a Biotage Creator XM microwave apparatus at 165° C. for 15 minutes. The reaction mixture was poured into water (60 mL), and the aqueous mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (0.5 g).

Aufarbeitung

  1. extractionthe aqueous mixture was extracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-7efc3d027cd1408baeec34c073293e2a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822521B2

Verknüpfte Notizen

Wird geladen…