HCID 12939743, compound → HCID 12939745, compound

HRID 847767Notes

Reaction equation

HRID 847767 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[S:10][CH:11]([C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH2:12][C:13]([OH:15])=[O:14]>FC(F)(F)C(O)=O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]2[N:1]3[C:9]4[C:4]([N:3]=[C:2]3[S:10][C:11]=2[CH2:12][C:13]([OH:15])=[O:14])=[N:5][CH:6]=[CH:7][CH:8]=4)=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 12939743HCID 12939743, compound

Product 1

HCID 12939745HCID 12939745, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

17 g (0.047 m) of 3-(imidazo[4,5-b]pyridine-2-ylthio)-3-(4-chlorobenzoyl)propionic acid, prepared according to Example 2, is dissolved in 200 ml trifluoroacetic acid, and the solution is heated to gentle reflux overnight. The solution is cooled and filtered, the solvent is removed in vacuo and the residual solid triturated with ether and the solid collected. The resulting trifluoroacetate is disproportionated in hot acetonitrile to give 9.3 g of title compound, m.p. 250°-252° C.

Workup

  1. temperaturethe solution is heated
  2. temperatureto gentle reflux overnight
  3. temperatureThe solution is cooled
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. customthe residual solid triturated with ether
  7. customthe solid collected

Sources & evidence

ORD record
ord-ed3f2308d1124396a094389c0bef8e52
Source dataset
uspto-grants-1981_10
Patent number
US04293696

Reaction notes

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