1,1'-Carbonyldiimidazole → HCID 14390336, compound

HRID 2073044Notes

Reaction equation

HRID 2073044 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:33][NH:34][CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([N:34]([CH3:33])[CH2:35][CH2:36][CH2:37][N:38]3[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]3)=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 7219854N-methyl-3-(4-methylpiperazin-1-yl)propan-1-amineHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390336HCID 14390336, compoundYield 19.8%

Procedure

Under nitrogen bubbling, a mixture of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (2.38 g, 0.008 mole) and 1,1'-carbonyldiimidazole (1.34 g, 0.008 mole) was stirred at room temperature for 3 hours. The N,4-dimethyl-1piperazinepropanamine (1.42 g, 0.008 mole) was added and the reaction mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was evaporated to dryness. The residue was partitioned between methylene chloride and aqueous potassium bicarbonate. The aqueous layer was separated and extracted with methylene chloride. The methylene chloride layers were combined, extracted with aqueous potassium bicarbonate and water and dried over sodium sulfate. The filtrate was evaporated and the solid residue was recrystallized as a fumarate salt from ethyl alcohol-isopropyl ether. Recrystallization from isopropyl alcohol-acetonitrile-isopropyl ether did not improve the analysis. The solid was converted to the free base. The free base was treated with boiling hexanes and allowed to cool to room temperature. The solid was collected by filtration, washed with hexane, and dried under high vacuum overnight to give 0.7 g of title compound, mp 114°-17° C.

Workup

  1. stirringto stir at room temperature for 2 hours
  2. customThe reaction mixture was evaporated to dryness
  3. customThe residue was partitioned between methylene chloride and aqueous potassium bicarbonate
  4. customThe aqueous layer was separated
  5. extractionextracted with methylene chloride
  6. extractionextracted with aqueous potassium bicarbonate and water
  7. dry with materialdried over sodium sulfate
  8. customThe filtrate was evaporated
  9. customthe solid residue was recrystallized as a fumarate salt from ethyl alcohol-isopropyl ether
  10. customRecrystallization from isopropyl alcohol-acetonitrile-isopropyl ether
  11. additionThe free base was treated with boiling hexanes
  12. temperatureto cool to room temperature
  13. filtrationThe solid was collected by filtration
  14. washwashed with hexane
  15. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-47f7f6663f1948afb10abab52e68b3ce
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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