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

HRID 235068Notes

Reaction equation

HRID 235068 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 3-amino-2-carbomethoxy-5-chlorothieno[3,2-b]pyridine, prepared as described in Example 62A (5g, 21 mmol) and sodium methoxide (4.5 g, 82 mmol) in MeOH (150 mL) were refluxed for 18 h. The reaction was concentrated and partitioned between EtOAc and NaHCO3 solution. The EtOAc layer was dried (MgSO4), filtered, concentrated, and chromatographed (5:1 hex: EtOAc) to yield 2.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ3.80 (s, 3H), 4.02 (s, 3H), 6.05 (bs, 2H), 6.89 (d, 1H), 7.88 (d, 1H); MS (DCI/NH3) m/e 239 (M+H)+.

Workup

  1. temperaturewere refluxed for 18 h
  2. concentrationThe reaction was concentrated
  3. custompartitioned between EtOAc and NaHCO3 solution
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed (5:1 hex: EtOAc)

Sources & evidence

ORD record
ord-47bd34b3281c456e8e1e2f51fc3392aa
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

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