Sodium ethoxide → 7-Hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester

HRID 902508Notes

Reaction equation

HRID 902508 reaction equation
[O-:1]CC.[Na+].[CH2:5]([O:7][C:8]([C:10]1[C:15](=[O:16])[N:14](CC2C=CC=C(F)C=2)[C:13]2[CH:25]=[CH:26][S:27][C:12]=2[C:11]=1N1CCNCC1)=[O:9])[CH3:6]>C(O)C>[CH2:5]([O:7][C:8]([C:10]1[C:15](=[O:16])[NH:14][C:13]2[C:25]([C:11]=1[OH:1])=[CH:26][S:27][CH:12]=2)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 167425624-(3-Fluoro-benzyl)-5-oxo-7-piperazin-1-yl-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 597020617-Hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (4.75 g, 66.34 mmol) was added to a solution of 4-(2-ethoxycarbonyl-acetylamino)-thiophene-3-carboxylic acid methyl ester (19) (8.57 g, 31.59 mmol) in anhydrous ethanol and refluxed overnight. The solution was cooled and excess solvent was distilled off The residue was dissolved in water and acidified by cold diluted HCl solution. The solids formed were filtered, washed by water and dried under vacuum at room temperature to get 4.3 g (57%) of 7-hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester as white solid. MP 193° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.27 (t, J=7.2 Hz, 3H), 4.28 (q, J=7.2 Hz, 2H), 6.83 (d, J=3.2 Hz, 1H), 8.24 (d, J=3.6 Hz, 1H), 11.10 (s, 1H), 12.90 (s, 1H) ppm; MS m/z=240 amu (M++1).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe solution was cooled
  3. distillationexcess solvent was distilled off The residue
  4. dissolutionwas dissolved in water
  5. customThe solids formed
  6. filtrationwere filtered
  7. washwashed by water
  8. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-58e4f109db8b4c079a343cfd8310b1ac
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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