1-Piperazinecarboxylic acid, ethyl ester → HCID 14390372, compound

HRID 2073071Notes

Reaction equation

HRID 2073071 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([O:35][C:36]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:37])[CH3:34]>O1CCCC1>[CH2:33]([O:35][C:36]([N:38]1[CH2:39][CH2:40][N:41]([C:18](=[O:20])[CH2:17][N:16]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:42][CH2:43]1)=[O:37])[CH3:34]

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390372HCID 14390372, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole), 1,1'carbonyldiimidazole (2.82 g, 0.0174 mole), and dry tetrahydrofuran (100 ml) was stirred at room temperature for two hours with nitrogen bubbling through it. A solution of ethyl-1-piperazine carboxylate (6.9 g, 0.0435 mole) in tetrahydrofuran (6 ml) was added dropwise and the reaction mixture was stirred at 50° C. overnight under nitrogen. The solvents were removed under reduced pressure and the residual oil was triturated in water (100 ml) overnight. The resulting solid was collected by filtration, rinsed with water, dissolved in hot isopropyl alcohol, and filtered hot. Water was added to the cloud point and upon cooling to room temperature, a solid precipitated, which was collected by filtration, rinsed with water, and dried under high vacuum to give 4.66 g (63%) of title compound, mp 184°-186° C.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. overnight under nitrogen
  2. customThe solvents were removed under reduced pressure
  3. customthe residual oil was triturated in water (100 ml) overnight
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed with water
  6. dissolutiondissolved in hot isopropyl alcohol
  7. filtrationfiltered hot
  8. additionWater was added to the cloud point
  9. temperatureupon cooling to room temperature
  10. customa solid precipitated
  11. filtrationwhich was collected by filtration
  12. washrinsed with water
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-e030dfe6d76043f0acc2c2fb50634900
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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