HCID 15027469, compound → 2-(4-Chlorophenyl)-3-[(pyridin-2-yl)methyl]-3H-imidazo[4,5-b]pyridine

HRID 973928Notes

Reaction equation

HRID 973928 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)=O)=[CH:4][CH:3]=1>C(O)CO>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 15027469HCID 15027469, compound

Product 1

HCID 150274702-(4-Chlorophenyl)-3-[(pyridin-2-yl)methyl]-3H-imidazo[4,5-b]pyridineYield 74.6%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 4-chloro-N-[2-[(2-pyridinylmethyl)amino]-3-pyridinyl]benzamide (14.65 g, 0.0433 mol) prepared in the previous paragraph and ethylene glycol (145 mL) were heated at reflux for 1.5 hr and then stirred at room temperature overnight. The resulting solid was collected by filtration, rinsed several times with water, recrystallized from isopropanol/water and dried under high vacuum at 70° C. to give 10.36 g (74% yield) of the title compound, mp 144°-146° C.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 1.5 hr
  3. filtrationThe resulting solid was collected by filtration
  4. washrinsed several times with water
  5. customrecrystallized from isopropanol/water
  6. customdried under high vacuum at 70° C.

Sources & evidence

ORD record
ord-cb45aed2e07444279c103851e13fde46
Source dataset
uspto-grants-1991_11
Patent number
US05066654

Reaction notes

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