Ethyl Acetate → HCID 11558927, Verbindung

HRID 550558

Reaktionsgleichung

Reaktionsgleichung von HRID 550558
[C:1]([C:3]1[CH:7]=[N:6][NH:5][C:4]=1[NH2:8])#[N:2].CN(C)[CH:11]=[CH:12][C:13]([C:15]1[CH:16]=[C:17]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=1)=O.C(OCC)(=O)C>C(O)(=O)C>[C:1]([C:3]1[CH:7]=[N:6][N:5]2[C:13]([C:15]3[CH:16]=[C:17]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)=[CH:12][CH:11]=[N:8][C:4]=12)#[N:2]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 855155-Amino-4-cyanopyrazoleHCID 67197697N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methyl-methanesulfonamide

Produkt 1

HCID 11558927HCID 11558927, VerbindungAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 0.1 g (0.93 mmol) of 4-cyano-2H-pyrazol-3-ylamine and 0.26 g (0.93 mmol) of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methyl-methanesulfonamide in 10 ml of glacial acetic acid was refluxed for 8 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 10 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 217 mg of N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-N-methyl-methanesulfonamide as a yellow solid (yield 71%; m.p.=193-195° C.).

Aufarbeitung

  1. temperaturewas refluxed for 8 hours
  2. customthe solvent was removed by reduced pressure distillation
  3. additionTo the resulting residue were added 10 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution
  4. customThe two layers were separated
  5. washthe aqueous layer was washed with 10 ml of dichloromethane
  6. washThe organic layers were washed with 10 ml of water
  7. dry with materialdried over magnesium sulfate
  8. customThe dichloromethane layer was evaporated to dryness
  9. customto yield an oil which

Quellen und Nachweise

ORD-Eintrag
ord-0b39a367e9244fb8b46a320d827267c8
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947688B2

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