1-Chlorobenzotriazole → N-[3-(3-chloropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide

HRID 1248802Notes

Reaction equation

HRID 1248802 reaction equation
[CH2:1]([N:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:18]3[N:19]=[CH:20][CH:21]=[C:17]3[N:16]=[CH:15][CH:14]=2)[CH:8]=1)[C:4](=[O:6])[CH3:5])[CH3:2].[Cl:22]N1C2C=CC=CC=2N=N1>ClCCl>[Cl:22][C:21]1[CH:20]=[N:19][N:18]2[C:13]([C:9]3[CH:8]=[C:7]([N:3]([CH2:1][CH3:2])[C:4](=[O:6])[CH3:5])[CH:12]=[CH:11][CH:10]=3)=[CH:14][CH:15]=[N:16][C:17]=12

Participants

4

Reactant 2

HCID 887611-ChlorobenzotriazoleHCID 13771261N-ethyl-N-(3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)acetamide

Product 1

HCID 13771278N-[3-(3-chloropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of N-ethyl-N-(3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)acetamide and 4.57 g of 1-chlorobenzotriazole in 50 ml of dichloromethane was refluxed for 25 minutes, then cooled and poured into 50 ml of ice-cold 2.5N aqueous sodium hydroxide. The mixture was filtered through hydrous magnesium silicate, precipitated with hexane and the solid collected, giving 0.7 g of the desired product, mp 157°-159°C.

Workup

  1. temperaturewas refluxed for 25 minutes
  2. temperaturecooled
  3. filtrationThe mixture was filtered through hydrous magnesium silicate
  4. customprecipitated with hexane
  5. customthe solid collected

Sources & evidence

ORD record
ord-2fbda73c370c47238ffc37811ddf81d2
Source dataset
uspto-grants-1986_12
Patent number
US04626538

Reaction notes

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