Tetrahydrofuran → N'-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-N,N-dimethylurea

HRID 8791

Reaktionsgleichung

Reaktionsgleichung von HRID 8791
[H-].[Na+].[NH2:3][C:4]1[C:12]2[C:7](=[N:8][C:9]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:11]=2)[O:6][C:5]=1[C:28]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:29].[CH3:36][N:37]([CH3:42])S(Cl)(=O)=O.C1[CH2:47][O:46]CC1>>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[C:12]3[C:4]([NH:3][C:47](=[O:46])[N:37]([CH3:42])[CH3:36])=[C:5]([C:28]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)=[O:29])[O:6][C:7]3=[N:8][C:9]=2[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])=[CH:18][CH:17]=1

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 9983227[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

Produkt 1

HCID 10437904N'-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-N,N-dimethylurea

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of sodium hydride (0.004 g; 60% dispersion; 0.111 mmol) in THF (0.5 mL) at 0° C. was added a solution of 0.050 g 0.101 mmol) of the product from Example 26 (in THF (0.5 mL) and the reaction mixture was stirred at 0° C. for 30 minutes. Dimethylsulfamoyl chloride (9 μL; 0.101 mmol) was added dropwise and the reaction was then stirred at room temperature for an additional 5 hours. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 50% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 564.9 (M+1), 566.9 (M+3); Rt=4.33 min.

Aufarbeitung

  1. stirringthe reaction was then stirred at room temperature for an additional 5 hours
  2. customThe reaction was quenched with saturated NaHCO3 solution
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by MPLC (silica gel; 0% to 50% ethyl acetate:hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-465b85b846ba480ab12263322a36681a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091216B2

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