HCID 14390504, compound → 2-(3,4-Dichlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

HRID 2073037Notes

Reaction equation

HRID 2073037 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]>C(O)CO>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[N:13]=[C:14]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[CH3:2]

Participants

3

Reactant 1

HCID 14390504HCID 14390504, compound

Product 1

HCID 143904732-(3,4-Dichlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of N-[3-[(3,4-dichlorobenzoyl)amino]-2-pyridinyl]glycine ethyl ester (33 g, 0.09 mole) and 167 ml of ethylene glycol was heated at reflux for 11/2 hr. The material crystallized upon cooling. A small portion of the solid was collected by filtration, washed with water, and dried under high vacuum. The solid was recrystallized from ethanol with refrigeration, collected by filtration, washed with ethanol/water mixture, and dried under high vacuum at 70° C. over 2 days to give 2.0 g, mp 141°-42° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 11/2 hr
  3. customThe material crystallized
  4. temperatureupon cooling
  5. filtrationA small portion of the solid was collected by filtration
  6. washwashed with water
  7. customdried under high vacuum
  8. customThe solid was recrystallized from ethanol with refrigeration
  9. filtrationcollected by filtration
  10. washwashed with ethanol/water mixture
  11. customdried under high vacuum at 70° C. over 2 days
  12. customto give 2.0 g, mp 141°-42° C.

Sources & evidence

ORD record
ord-da23487baae24eaf97f9d78fe70c5929
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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