Potassium Carbonate → 4-(3-Chloro-phenyl)-2-[6-(3-pyrrolidin-1-yl-propoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide

HRID 1667750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667750
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[CH:12][N:11]([C:14]3[S:15][C:16]([C:26]([NH2:28])=[O:27])=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[N:18]=3)[C:10]=2[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>[I-].[K+].CN(C)C=O>[Cl:25][C:21]1[CH:20]=[C:19]([C:17]2[N:18]=[C:14]([N:11]3[C:10]4[CH:29]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)[CH:7]=[CH:8][C:9]=4[N:13]=[CH:12]3)[S:15][C:16]=2[C:26]([NH2:28])=[O:27])[CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 674272962-[6-(3-Chloro-propoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

Produkt 1

HCID 468317684-(3-Chloro-phenyl)-2-[6-(3-pyrrolidin-1-yl-propoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amideAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.043 g (0.1 mmole) of 2-[6-(3-chloro-propoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.34a), 1 mL of dimethylformamide, 0.069 g (0.5 mmole) of potassium carbonate, 0.001 g of potassium iodide and 0.025 mL (0.3 mmole) of pyrrolidine was stirred at 100 degrees for 6 hours. The mixture was concentrated under reduced pressure, and diluted with 20 mL of water. The precipitate was collected by filtration and the solid triturated with diethyl ether to give 0.036 g of 4-(3-chloro-phenyl)-2-[6-(3-pyrrolidin-1-yl-propoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.34) as a white solid. MH+/Z=482

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with 20 mL of water
  3. filtrationThe precipitate was collected by filtration
  4. customthe solid triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6c6b68102b0f4ae9a708fcadb112008f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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