Diisopropylethylamine → HCID 23325339, compound

HRID 1380527Notes

Reaction equation

HRID 1380527 reaction equation
[N:1]1([C:7]2[N:21]=[C:10]3[N:11]=[CH:12][CH:13]=[C:14]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)[N:9]3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH:23]([CH2:33][CH3:34])[C:24]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)=[O:25].C(N(CC)C(C)C)(C)C>CC(O)C>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:24](=[O:25])[CH2:23][CH2:33][CH2:34][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[N:21]=[C:10]4[N:11]=[CH:12][CH:13]=[C:14]([C:15]5[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=5)[N:9]4[N:8]=3)[CH2:6][CH2:5]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13686022HCID 13686022, compoundHCID 15459067HCID 15459067, compound

Product 1

HCID 23325339HCID 23325339, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5.6 g (0.02 moles) of 2-(1-piperazinyl)-7-(4-pyridyl)[1,2,4]triazolo[1,5-a]pyrimidine (prepared as described in Example 47), 4.0 g (0.02 moles) of α-chloro-p-fluorobutyrophenone, 3.6 g (0.027 moles) of N,N-diisopropylethylamine and 100 ml of 2-propanol was heated at reflux for 16 hours with stirring. The reaction mixture was evaporated in vacuo to a solid. The solid was dissolved in 100 ml of water and extracted twice with 100 ml of chloroform. The extracts were combined, dried over magnesium sulfate, filtered and evaporated to a dark syrup. The syrup was dissolved in dichloromethane and passed through a pad of magnesium silicate, washing with methylene chloride. This filtrate was collected and set aside. Then acetone was passed through the pad and the acetone filtrate was collected and evaporated to a syrup. The syrup was dissolved in 15 ml of ethanol, 200 ml of ether was added, then hexane until cloudy. Evaporation by boiling caused crystallization. The crude product was collected and washed with ether. Recrystallization from ethanol gave 1.2 g of the desired product as yellow crystals, mp 133°-135° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe reaction mixture was evaporated in vacuo to a solid
  4. dissolutionThe solid was dissolved in 100 ml of water
  5. extractionextracted twice with 100 ml of chloroform
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to a dark syrup
  9. dissolutionThe syrup was dissolved in dichloromethane
  10. washwashing with methylene chloride
  11. customThis filtrate was collected
  12. customthe acetone filtrate was collected
  13. customevaporated to a syrup
  14. dissolutionThe syrup was dissolved in 15 ml of ethanol
  15. addition200 ml of ether was added
  16. customEvaporation
  17. customcrystallization
  18. customThe crude product was collected
  19. washwashed with ether
  20. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-22628a08a17e464d86ca0921d52e4eed
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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