Thiazolidinedione → HCID 178432895, Verbindung

HRID 383661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383661
[CH3:1][C:2]1[N:3]([C:7]2[CH:8]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][N:17]4[N:20]=[CH:21][C:22]([CH:23]=O)=[C:16]4[N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH:4]=[CH:5][N:6]=1.[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCCC1>CCO.CN(C=O)C>[CH3:1][C:2]1[N:3]([C:7]2[CH:8]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][N:17]4[N:20]=[CH:21][C:22]([CH:23]=[C:29]5[S:25][C:26](=[O:31])[NH:27][C:28]5=[O:30])=[C:16]4[N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH:4]=[CH:5][N:6]=1

Komponenten

6

Edukt 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 581967575-(3-(2-methyl-1H-imidazol-1-yl)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Produkt 1

HCID 178432895HCID 178432895, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 5-(3-(2-methyl-1H-imidazol-1-yl)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (48 mg, 0.151 mmol) in 0.5 mL EtOH was added 2,4-thiazolidinedione (18 mg, 0.151 mmol) and piperidine (15 μL, 0.151 mmol). The mixture was heated at 70° C. overnight. The solid formed was isolated by filtration and dissolved in DMF. Insolubilities were filtered off and the resulting filtrate purified by HPLC to yield 5-((5-(3-(2-methyl-1H-imidazol-1-yl)phenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione. LCMS (M+1=418)

Aufarbeitung

  1. customThe solid formed
  2. customwas isolated by filtration
  3. filtrationInsolubilities were filtered off
  4. customthe resulting filtrate purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4f505a45e365492896d897e4d6e43f7b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367681B2

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