Dimethylformamide → HCID 10256229, Verbindung

HRID 8795

Reaktionsgleichung

Reaktionsgleichung von HRID 8795
NC1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[O:27].[H-].[Na+].IC.[CH3:38][N:39]([CH:41]=O)[CH3:40]>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[C:10]3[C:41]([N:39]([CH3:38])[CH3:40])=[C:3]([C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:27])[O:4][C:5]3=[N:6][C:7]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:16][CH:15]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9983227[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

Produkt 1

HCID 10256229HCID 10256229, Verbindung

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 0.050 g (0.101 mmol) of the product from Example 26 in DMF (1 mL) at 0° C. was treated with sodium hydride (0.008 g; 60% dispersion; 0.213 mmol). After the addition, the reaction mixture was stirred for 20 minutes at 0° C., and then treated with iodomethane (19 μL; 0.303 mmol). The reaction was warmed to room temperature and stirred for 1 h. 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: 521.9 (M+1), 523.9 (M+3); Rt=3.96 min.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThe reaction was warmed to room temperature
  3. stirringstirred for 1 h
  4. customThe reaction was quenched with saturated NaHCO3 solution
  5. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  6. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by MPLC (silica gel; 0% to 50% ethyl acetate-hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9ab14d756ba14936bc6b2f503da78bc2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091216B2

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