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

HRID 621969Notes

Reaction equation

HRID 621969 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-6edee5bf22f2462b833c842af2b8fbcc
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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