Dichloromethane → 6-{6-bromo-5-[(dimethyl-lambda~4~-sulfanylidene)amino]-3-phenyl-2-pyrazinyl}-2-isopropyl-3 (2H)-pyridazinone

HRID 915050

Reaktionsgleichung

Reaktionsgleichung von HRID 915050
FC(F)(F)S(O[S:7]([C:10](F)(F)F)(=O)=O)(=O)=O.[NH2:16][C:17]1[N:18]=[C:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:20]([C:24]2[CH:25]=[CH:26][C:27](=[O:33])[N:28]([CH:30]([CH3:32])[CH3:31])[N:29]=2)=[N:21][C:22]=1[Br:23].[CH2:40](Cl)Cl>CS(C)=O.CC(C)=O>[Br:23][C:22]1[N:21]=[C:20]([C:24]2[CH:25]=[CH:26][C:27](=[O:33])[N:28]([CH:30]([CH3:32])[CH3:31])[N:29]=2)[C:19]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[N:18][C:17]=1[N:16]=[S:7]([CH3:10])[CH3:40]

Komponenten

6

Edukt 3

HCID 6344Dichloromethane2×HCID 67749Trifluoromethanesulfonic anhydrideHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Produkt 1

HCID 877986596-{6-bromo-5-[(dimethyl-lambda~4~-sulfanylidene)amino]-3-phenyl-2-pyrazinyl}-2-isopropyl-3 (2H)-pyridazinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-55 °C

Versuchsvorschrift

To a solution of DMSO (0.75 ml) in CH2Cl2 (5 ml) was added trifluoromethanesulfonic anhydride (1.5 ml) dropwise at <−75° C. under nitrogen. A suspension of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (3.00 g) in a mixture of DMSO (5 ml) and CH2Cl2 (6 ml) was added and stirred at −65° C. for 2 hours and at −55° C. for one hour. The reaction mixture was quenched with 1N aq. NaOH (20 ml) and stirred at 15° C. for 10 minutes. An organic layer was collected, dried over MgSO4 and concentrated under reduced pressure to give a solid. The solid was suspended in acetone and collected by filtration to give 6-{6-bromo-5-[(dimethyl-lambda˜4˜-sulfanylidene)amino]-3-phenyl-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone (3.16 g).

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was quenched with 1N aq. NaOH (20 ml)
  3. stirringstirred at 15° C. for 10 minutes
  4. customAn organic layer was collected
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid
  8. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-38ecb570399c4ff8acabdb50667aacbb
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265120B2

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