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Ethyl Acetate → N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-methane-sulfonamide

HRID 550559
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 550559
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8].C(C1C=NN2[C:24]([C:25]3[CH:26]=[C:27]([N:31]([CH3:36])[S:32]([CH3:35])(=[O:34])=[O:33])[CH:28]=[CH:29][CH:30]=3)=[CH:23][CH:22]=NC=12)#N.C(OCC)(=O)C>C(O)(=O)C>[CH3:36][N:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:24]2[N:6]3[N:5]=[CH:4][C:3]([C:7]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[O:8])=[C:2]3[N:1]=[CH:22][CH:23]=2)[CH:26]=1)[S:32]([CH3:35])(=[O:33])=[O:34]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 11550150(5-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanoneHCID 11558927N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-N-methyl-methanesulfonamide

Produkt 1

HCID 11690123N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-methane-sulfonamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Versuchsvorschrift

A mixture of 0.1 g (0.52 mmol) of (5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone and 0.146 g (0.93 mmol) of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methyl-methanesulfonamide (obtained as described in Example 2) 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 178 mg N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-methane-sulfonamide as a yellow solid (yield 83%; m.p.=169-170° 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-bbc56dbcf8a24748a59c41fc0a744687
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07947688B2

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