Ethyl Thioglycolate → HCID 21948185, compound

HRID 1063577Notes

Reaction equation

HRID 1063577 reaction equation
[NH:1]([C:8]1[N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14](Cl)[N:13]=[C:12]([CH3:20])[CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CCO>[NH:1]([C:8]1[N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([S:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:13]=[C:12]([CH3:20])[CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12185Ethyl ThioglycolateHCID 10269984HCID 10269984, compound

Product 1

HCID 21948185HCID 21948185, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-anilino-5-chloro-7-methyl-1-phenyl-1,6-naphthyridin-4(1H)-one (200 mg, 0.55 mmol) in EtOH (10 mL) was added ethyl 2-mercaptoacetate (0.12 mL, 1.10 mmol) and TEA (0.23 mL, 1.65 mmol). The reaction was heated at reflux for 24 h. The reaction mixture was cooled, concentrated in vacuo, diluted with water and extracted is with EtOAc. The combined organic extracts were washed with water, brine, and dried over Na2SO4. Solvents were removed in vacuo and the residue was purified by reverse-phase preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min) to provide ethyl [(2-anilino-7-methyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridin-5-yl)sulfanyl]acetate (120 mg, 49%): LCMS RT: 3.07 min, MH+: 446.2.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additiondiluted with water
  6. extractionextracted
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried over Na2SO4
  9. customSolvents were removed in vacuo
  10. customthe residue was purified by reverse-phase preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min)

Sources & evidence

ORD record
ord-2dae2cf157894ecfad021b0284be5329
Source dataset
uspto-grants-2005_11
Patent number
US06964971B2

Reaction notes

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