Sodium hydride → ethyl 5-[(3-methoxypropyl)amino]-1-phenyl-1H-pyrazole-4-carboxylate

HRID 2192837Notes

Reaction equation

HRID 2192837 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][O:24][CH3:25]>CN(C=O)C>[CH3:25][O:24][CH2:23][CH2:22][CH2:21][NH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 85270Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylateHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 59625449ethyl 5-[(3-methoxypropyl)amino]-1-phenyl-1H-pyrazole-4-carboxylateYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate (1.26 g) was dissolved in DMF (10 ml), NaH (0.25 g) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min. 1-Bromo-3-methoxypropane (0.83 g) was added to the reaction mixture under ice-cooling, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:10-4:6) was concentrated under reduced pressure to give the object compound (1.1 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at 60° C. for 1 hr
  4. concentrationThe reaction mixture was concentrated
  5. washthe fraction eluted with ethyl acetate-hexane (0:10-4:6)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-02fbfb1f3dab4070894e3fb340e8526f
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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