Potassium Hydroxide → HCID 123151441, compound

HRID 2178542Notes

Reaction equation

HRID 2178542 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[C:6]([NH2:11])=[N:7][N:8]([CH3:10])[CH:9]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][O:2][CH:3]=[CH:4][C:5]1[C:6]([N:11]2[CH2:13][CH2:14][CH2:15][CH2:16][C:17]2=[O:18])=[N:7][N:8]([CH3:10])[CH:9]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 5211735-Bromovaleryl chlorideHCID 123776242HCID 123776242, compound

Product 1

HCID 123151441HCID 123151441, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-(2-methoxyvinyl)-1-methyl-1H-pyrazol-3-amine a17-1 (500 mg, 3.27 mmol, 1 eq), 5-bromovaleryl chloride (651.9 mg, 3.27 mmol, 1 eq), potassium hydroxide (550.1 mg, 9.80 mmol, 3 eq), 4-dimethymaminopyridine (39.9 mg, 0.33 mmole, 0.1 eq) and N,N,N-tributylbutan-1-aminium bromide (105.3 mg, 0.33 mmole, 0.1 eq) in toluene (15 ml) is heated to reflux overnight. After filtration and evaporation the residue is purified by reverse phase chromatography (basic mode, gradient: H2O/acetonitrile/NH4OH from 80/20/0.1 to 50/50/0.1 in 10 minutes) to afford 1-[4-(2-methoxyvinyl)-1-methyl-1H-pyrazol-3-yl]piperidin-2-one a17-2.

Workup

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. filtrationAfter filtration and evaporation the residue
  4. customis purified by reverse phase chromatography (basic mode, gradient: H2O/acetonitrile/NH4OH from 80/20/0.1 to 50/50/0.1 in 10 minutes)

Sources & evidence

ORD record
ord-5bc34d1fd7f54b8da76c41e169fe5159
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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