Hydrogen Bromide → HCID 13686023, compound

HRID 1380524Notes

Reaction equation

HRID 1380524 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:31]=[C:20]3[N:21]=[CH:22][CH:23]=[C:24]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[N:19]3[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.Br>CCOCC>[N:14]1([C:17]2[N:31]=[C:20]3[N:21]=[CH:22][CH:23]=[C:24]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[N:19]3[N:18]=2)[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13686005HCID 13686005, compound

Product 1

HCID 13686023HCID 13686023, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 2.5 g amount of 4-[7-(3-pyridyl)[1,2,4]-triazolo[1,5-a]pyrimidin-2-yl]-1-piperazinecarboxylic acid benzyl ester was added 5.0 ml of hydrobromic acid (31% in glacial acetic acid). The mixture was allowed to react for 4 hours then was cooled to room temperature. Anhydrous ether was added, the mixture was swirled and the liquid decanted. This step was repeated several times. The residual precipitate was dissolved in water and the solution was filtered. The filtrate was made basic with 5N sodium hydroxide and extracted several times with dichloromethane. The extracts were combined and heated to boiling, then hexane was added to crystallize the product. Cooling and filtration gave 1.10 g of the deseired product as pale yellow crystals, mp 156°-158° C.

Workup

  1. customto react for 4 hours
  2. customthe liquid decanted
  3. dissolutionThe residual precipitate was dissolved in water
  4. filtrationthe solution was filtered
  5. extractionextracted several times with dichloromethane
  6. temperatureheated
  7. additionhexane was added
  8. customto crystallize the product
  9. temperatureCooling
  10. filtrationfiltration

Sources & evidence

ORD record
ord-93fc97a3037642108237da0c3777044c
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

Loading…