Hydrochloric Acid → 3-Tert-butyl-1-[3-(2-morpholinoethyl)phenyl]-1h-pyrazol-5-amine

HRID 16998

Reaktionsgleichung

Reaktionsgleichung von HRID 16998
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:12]=[C:13]([CH2:17][C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=O)[CH:14]=[CH:15][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].B.CSC.Cl.[OH-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 218673452-[3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl]-1-morpholinoethanone

Produkt 1

HCID 187235713-Tert-butyl-1-[3-(2-morpholinoethyl)phenyl]-1h-pyrazol-5-amineAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of Example L (1.2 g, 3.5 mmol) in THF (6 ml) was added borane-methylsulfide (9 mmol). The mixture was heated to reflux for 90 min and cooled to RT, and 6 N HCl was added and heated to reflux for 10 min. The mixture was basified by adding sodium hydroxide, followed by extraction with ethyl acetate. The organic layer was dried (Na2SO4) filtered and concentrated in vacuo to yield 3-tert-butyl-1-[3-(2-morpholinoethyl)phenyl]-1H-pyrazol-5-amine (0.78 g), which was used without further purification.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 90 min
  3. temperatureheated
  4. temperatureto reflux for 10 min
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3bebb7ebbeca4f5cbddb5163e7080e71
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737283B2

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