Ammonia → 2-(2-Methoxy-4-methanesulfonylamino-phenyl)-6-hydroxy-imidazo[4,5-b]pyridine

HRID 35203Notes

Reaction equation

HRID 35203 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([O:9]C(=O)C)=[CH:4][N:3]=1.[CH3:13][O:14][C:15]1[CH:23]=[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:20][C:16]=1[C:17](O)=O.N>P(Cl)(Cl)(Cl)=O>[CH3:13][O:14][C:15]1[CH:23]=[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:20][C:16]=1[C:17]1[NH:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[C:5]([OH:9])[CH:6]=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 121193062-Methoxy-4-[(methylsulfonyl)amino]benzoic acidHCID 21295798HCID 21295798, compound

Product 1

HCID 133928232-(2-Methoxy-4-methanesulfonylamino-phenyl)-6-hydroxy-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

0.5 g of 2,3-diamino-5-acetoxy-pyridine and 0.83 g of 2-methoxy-4-methanesulfonylamino-benzoic acid were refluxed for one hour in 20 ml of phosphorus oxychloride. The reaction mixture was combined with ice water and then ad]usted to pH 7 with concentrated aqueous ammonia. The product was then extracted with ethyl acetate and purified by column chromatography (silica gel, eluant: methylene chloride/ethanol 1:0.02 to 1:0.1). Yield: 0.06 g (6% of theory). Melting point: 225° C. (decomp.).

Workup

  1. extractionThe product was then extracted with ethyl acetate
  2. custompurified by column chromatography (silica gel, eluant: methylene chloride/ethanol 1:0.02 to 1:0.1)

Sources & evidence

ORD record
ord-3e9ca9e05ccf4124881197babf203589
Source dataset
uspto-grants-1988_08
Patent number
US04766130

Reaction notes

Loading…