2,5-Dimethyl-1-phenylpyrrole-3-carboxaldehyde → Pyrvinium Pamaote Impurity 3

HRID 641810

Reaktionsgleichung

Reaktionsgleichung von HRID 641810
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=[CH:11][C:4]=2[N:3]=1.[CH3:15][C:16]1[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]([CH3:23])=[CH:19][C:20]=1[CH:21]=O>CN(C=O)C.[OH-].[Na+].[Cl-].[Cl-].[Zn+2]>[CH3:14][N:12]([CH3:13])[C:9]1[CH:8]=[C:5]2[C:4](=[CH:11][CH:10]=1)[N:3]=[C:2](/[CH:1]=[CH:21]/[C:20]1[CH:19]=[C:18]([CH3:23])[N:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]=1[CH3:15])[CH:7]=[CH:6]2

Komponenten

6

Edukt 2

HCID 665152,5-Dimethyl-1-phenylpyrrole-3-carboxaldehydeHCID 667256-Quinolinamine, N,N,2-trimethyl-

Produkt 1

HCID 25015775Pyrvinium Pamaote Impurity 3Ausbeute 2,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of compound 3 (316 mg, 1.7 mmol) and compound 5 (507 mg, 2.55 mmol) in DMF (25 mL) was added ZnCl2 (232 mg, 1.7 mmol). The reaction mixture was stirred at 160° C. overnight. Then the reaction mixture was diluted with aqueous NaOH (10%) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure, the residue was purified by column chromatography (hexane: EtOAc=20:1) to give 13 mg of the target product (2.1%). MS [M++1]=368, LC-MS: tR=1.909 min

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography (hexane: EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-542751499db846c49ec3256d8634c523
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696227B2

Verknüpfte Notizen

Wird geladen…