3-Amino-5-chlorothieno[3,2-b]pyridine-2-carboxylic acid methyl ester → HCID 10847520, compound

HRID 367285Notes

Reaction equation

HRID 367285 reaction equation
[NH2:1][C:2]1[C:6]2=[N:7][C:8](Cl)=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:16][O-:17].[Na+]>CO>[NH2:1][C:2]1[C:6]2=[N:7][C:8]([O:17][CH3:16])=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 107527153-Amino-5-chlorothieno[3,2-b]pyridine-2-carboxylic acid methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 10847520HCID 10847520, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-amino-5-chloro-thieno[3,2-b]pyridine-2-carboxylate, prepared according to the procedure in Example 10A (5 g, 21 mmol) and sodium methoxide (4.5 g, 82 mmol) in methanol (150 mL) was refluxed for 18 hours, concentrated and partitioned between ethyl acetate and saturated aqueous NaHCO3. The ethyl acetate layer was dried (MgSO4) and concentrated, and the residue was chromatographed on silica gel with 5:1 hexanes/ethyl acetate to provide the title compound. MS (DCI/NH3) m/e 239 (M+H)+.

Workup

  1. temperaturewas refluxed for 18 hours
  2. concentrationconcentrated
  3. custompartitioned between ethyl acetate and saturated aqueous NaHCO3
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was chromatographed on silica gel with 5:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-ef0bcc59f8c54d79ae4407aed207138d
Source dataset
uspto-grants-2000_10
Patent number
US06133275

Reaction notes

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