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

HRID 16998

Reaction equation

HRID 16998 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 187235713-Tert-butyl-1-[3-(2-morpholinoethyl)phenyl]-1h-pyrazol-5-amineYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3bebb7ebbeca4f5cbddb5163e7080e71
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Linked notes

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