HCID 22677353, compound → HCID 178499074, compound

HRID 1837455Notes

Reaction equation

HRID 1837455 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]([O:14]C(C)(C)C)=[CH:12][CH:13]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23]>C1COCC1.FC(F)(F)C(O)=O>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23]

Participants

4

Reactant 1

HCID 22677353HCID 22677353, compound

Product 1

HCID 178499074HCID 178499074, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-amino-3-chloro-6-(6-t-butoxy-3-pyridinyl)pyridine-2-carboxylate (0.50 g, 1.49 mmol) was dissolved in a 1:1 mixture of THF and trifluoroacetic acid (5 mL) and heated to reflux for 30 minutes. The volatiles were removed in vacuo and the crude material was purified by HPLC (linear gradient, 100% water to 100% acetonitrile) to give of methyl 4-amino-3-chloro-6-(6-hydroxy-3-pyridinyl)pyridine-2-carboxylate (0.35 g, 1.25 mmol): Mp 251-52° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. customThe volatiles were removed in vacuo
  4. customthe crude material was purified by HPLC (linear gradient, 100% water to 100% acetonitrile)

Sources & evidence

ORD record
ord-f3798b3217e649cdb44fe984b46b0639
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

Loading…