Potassium Phosphate, Tribasic → HCID 46897014, Verbindung

HRID 242025

Reaktionsgleichung

Reaktionsgleichung von HRID 242025
[S:1]1[CH:5]=[C:4]([C:6]2[N:11]=[CH:10][C:9]([CH2:12][N:13]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:16]4=[N:23][NH:24][C:25](=[O:26])[C:15]4=[N:14]3)=[CH:8][CH:7]=2)[N:3]=[CH:2]1.I[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:29]=1[CH3:35].CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.[Cu]I>[CH3:35][C:29]1[C:30]([CH3:34])=[CH:31][CH:32]=[CH:33][C:28]=1[N:24]1[C:25](=[O:26])[C:15]2=[N:14][N:13]([CH2:12][C:9]3[CH:10]=[N:11][C:6]([C:4]4[N:3]=[CH:2][S:1][CH:5]=4)=[CH:7][CH:8]=3)[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]2=[N:23]1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 1416452,3-DimethyliodobenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86660007HCID 86660007, Verbindung

Produkt 1

HCID 46897014HCID 46897014, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-{[6-(1,3-Thiazol-4-yl)pyridin-3-yl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one (66 mg, 0.18 mmol) was dissolved in degassed N,N-dimethylformamide (1 mL) and copper (I) iodide (35 mg, 0.22 mmol, 1.2 equiv), 1-iodo-2,3-dimethylbenzene (51 mg, 0.22 mmol, 1.2 equiv), (±)-trans-N,N′-dimethylcyclohexane-1,2-diamine (78 mg, 0.549 mmol, 3 equiv) and potassium phosphate (0.27 g, 1.3 mmol, 7 equiv) were added. The vessel was sealed and placed into an oil bath preheated at 105° C. for 40 minutes. The mixture cooled to ambient temperature, diluted with water (5 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed three times with water and once with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 96:4; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.87 (1H, s), 8.69 (1H, s), 8.31 (1H, d, J=8.2 Hz), 8.16 (2H, m), 7.77 (1H, d, J=8.2 Hz), 7.57 (4H, m), 7.28 (1H, m), 7.22 (1H, d, J=3.9 Hz), 5.90 (2H, s), 2.37 (3H, s), 2.21 (3H, s) ppm; high resolution mass spectrometry (ES+) m/z 465.1499 [(M+H)+; calculated for C26H21N6OS: 465.1492].

Aufarbeitung

  1. customThe vessel was sealed
  2. customplaced into an oil bath
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washThe combined organic extracts were washed three times with water
  5. dry with materialonce with brine, dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 96:4; chloroform:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-59e5ed3b13fb4f53841c91f63b62f296
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653079B2

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