Ethanol → HCID 76814775, Verbindung

HRID 1878520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878520
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:31][NH2:32].[CH2:33](O)[CH3:34]>>[CH3:4][C:16]1[CH:15]=[C:17]([CH:18]=[CH:33][CH:34]=1)[CH:22]=[N:31][NH:32][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 58531082HCID 58531082, Verbindung

Produkt 1

HCID 76814775HCID 76814775, Verbindung

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

There was suspended, in ethanol (2 mL), 5-chloro-2-(4-methylphenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (50.0 mg, 0.152 mM) and then potassium carbonate (23.1 mg, 0.152 mM) and hydrazine monohydrate (36.9 μL, 0.760 mM) were added to the resulting suspension. This suspension was stirred at 150° C. for 20 minutes under the irradiation with microwaves, diluted with a saturated common salt aqueous solution and then extracted with ethyl acetate. The extracts thus obtained were combined, dried over anhydrous sodium sulfate and then the solvent was distilled off. The resulting residue was suspended in ethanol (2 mL), then acetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (17.9 μL, 0.152 mM) were added to the suspension and then the resulting mixture was stirred at room temperature for one hour. This reaction mixture was filtered and then the resulting solid was purified by the NH-silica gel column chromatography (methylene chloride) to thus give the title compound (31.4 mg, overall yield of these two steps: 48%).

Aufarbeitung

  1. additiondiluted with a saturated common salt aqueous solution
  2. extractionextracted with ethyl acetate
  3. customThe extracts thus obtained
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. additionacetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (17.9 μL, 0.152 mM) were added to the suspension
  7. stirringthe resulting mixture was stirred at room temperature for one hour
  8. filtrationThis reaction mixture was filtered
  9. customthe resulting solid was purified by the NH-silica gel column chromatography (methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-9f541a86439e413396e917ce5b62955c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314098B2

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