Phosphorus oxychloride → HCID 69233946, compound

HRID 1178620Notes

Reaction equation

HRID 1178620 reaction equation
[C:1]([C:3]1[C:4](=O)[C:5]2[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[S:9][C:6]=2[NH:7][CH:8]=1)#[N:2].P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[CH3:18][O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:10]1[S:9][C:6]2=[N:7][CH:8]=[C:3]([C:1]#[N:2])[C:4]([Cl:22])=[C:5]2[CH:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22256643Methyl 4-(5-cyano-4-oxo-4,7-dihydrothieno[2,3-b]pyridin-2-yl)butanoate

Product 1

HCID 69233946HCID 69233946, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of methyl 4-(5-cyano-4-oxo-4,7-dihydrothieno[2,3-b]pyridin-2-yl)butanoate (136 mg) and 2 drops of N,N-dimethylformamide in 5 mL of phosphorous oxychloride is heated at reflux for 10 minutes and concentrated. To the residue is added dichloromethane and the solution is washed with 1% aqueous sodium bicarbonate solution. The organic layer is dried and concentrated. The residue is purified by flash column chromatography eluting with dichloromethane to provide 126 mg of 4-(4-chloro-5-cyano-thieno[2,3-b]pyridin-2-yl)-butyric acid methyl ester as a tan solid, mp 55–57° C.; 1H NMR (DMSO-d6) δ 1.98 (quintet, J=7 Hz, 2H), 2.42 (t, J=7 Hz, 2H), 3.04 (t, J=7 Hz, 2H), 3.59 (s, 3H), 7.42 (s, 1H), 8.94 (s, 1H); MS 295.1 (M+H)+

Workup

  1. temperatureis heated
  2. temperatureat reflux for 10 minutes
  3. concentrationconcentrated
  4. additionTo the residue is added dichloromethane
  5. washthe solution is washed with 1% aqueous sodium bicarbonate solution
  6. customThe organic layer is dried
  7. concentrationconcentrated
  8. customThe residue is purified by flash column chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-b6cf61062cdb47f29066f1a862a893c9
Source dataset
uspto-grants-2007_10
Patent number
US07276519B2

Reaction notes

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