2,3-Diaminopyridine → 2-(2'-Methoxy-4'-chlorosulfonyl-phenyl)-imidazo[4,5-b]pyridine hydrochloride

HRID 2309860Notes

Reaction equation

HRID 2309860 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:12]([Cl:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5](O)=O.NC1C=CC(C(O)=O)=C(OC)C=1.[NH2:28][C:29]1[C:34]([NH2:35])=[CH:33][CH:32]=[CH:31][N:30]=1>P(Cl)(Cl)(Cl)=O>[ClH:15].[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:12]([Cl:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]1[NH:35][C:34]2[C:29]([N:28]=1)=[N:30][CH:31]=[CH:32][CH:33]=2

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 755994-Amino-o-anisic acidHCID 201845804-(Chlorosulfonyl)-2-methoxybenzoic acid

Product 1

HCID 201845172-(2'-Methoxy-4'-chlorosulfonyl-phenyl)-imidazo[4,5-b]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

Five grams of 2-methoxy-4-chlorosulfonyl-benzoic acid (prepared from 4-amino-2-methoxy-benzoic acid via the corresponding diazonium compound) were dissolved in 400 ml of phosphorus oxychloride and heated to 80° C. for 30 minutes. Then, 3.6 mg of 2,3-diaminopyridine were added, and the mixture was refluxed for four hours. The reaction mixture was concentrated by evaporation in vacuo and re-evaporated with toluene, and the solid residue was processed further without any other purification.

Workup

  1. temperaturethe mixture was refluxed for four hours
  2. concentrationThe reaction mixture was concentrated by evaporation in vacuo
  3. customre-evaporated with toluene
  4. customthe solid residue was processed further without any other purification

Sources & evidence

ORD record
ord-5f3989f4c3714807afddf293f35354b6
Source dataset
uspto-grants-1987_09
Patent number
US04696931

Reaction notes

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