Water → HCID 53915798, compound

HRID 1646253Notes

Reaction equation

HRID 1646253 reaction equation
CI.[NH2:3][C:4]1[CH:5]=[C:6]([C:10]2[C:18]([CH:19]=[CH:20][C:21]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]3[CH2:29][CH3:30])=[O:22])=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1.[C:31](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:31][NH:3][C:4]1[CH:5]=[C:6]([C:10]2[C:18]([CH:19]=[CH:20][C:21]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]3[CH2:29][CH3:30])=[O:22])=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54504670HCID 54504670, compound

Product 1

HCID 53915798HCID 53915798, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyliodide (0.84 g) in N,N-dimethylformamide (2 ml) was added dropwise to a stirred mixture of 1-[3-{2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl}acryloyl]-2-ethylpiperidine (trans isomer) (1.50 g) and powdered potassium carbonate (0.28 g) in N,N-dimethylformamide (10 ml) at room temperature. After being stirred at room temperature for 2 hours and 50 minutes, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (36 g) with a mixture of methylene chloride and acetonitrile (5:1) as an eluent. The fractions containing major product were combined and evaporated in vacuo to give crystals of 1-[3-{2-(3-methylaminophenyl)pyrazolo[1,5-a]pyridin-3-yl}acryloyl]-2-ethylpiperidine (trans isomer) (0.21 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel (36 g) with a mixture of methylene chloride and acetonitrile (5:1) as an eluent
  6. additionThe fractions containing major product
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-e438d41da4604b52b720e5b66269725d
Source dataset
uspto-grants-1993_01
Patent number
US05179103

Reaction notes

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