1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one → HCID 11437510, compound

HRID 1278230Notes

Reaction equation

HRID 1278230 reaction equation
C[N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.NC1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH3:25])[NH:17][N:16]=1>C(O)(=O)C>[CH2:23]([O:22][C:20]([C:19]1[C:18]([CH3:25])=[N:17][N:16]2[C:5]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=[N:2][C:13]=12)=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 683559ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 11437510HCID 11437510, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 9.09 g. of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one and 2.54 g. of ethyl 3-amino-5-methylpyrazole-4-carboxylate in 25 ml. of glacial acetic acid is refluxed for 16 hours. The solvent is removed and the residue in dichloromethane is washed with saturated sodium bicarbonate solution. The dichloromethane solution is passed through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give 3.1 g. of the product of the example, m.p. 145°-146° C.

Workup

  1. additionA mixture of 9.09 g
  2. customThe solvent is removed
  3. washthe residue in dichloromethane is washed with saturated sodium bicarbonate solution
  4. concentrationThe eluent is concentrated
  5. additionhexane added
  6. customto give 3.1 g

Sources & evidence

ORD record
ord-9d2d14c7863045e2b20f1bcdd1938b98
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Reaction notes

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