Acetic Acid → HCID 46244244, compound

HRID 2366059Notes

Reaction equation

HRID 2366059 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].O=[C:10]1[CH2:14][S:13][CH2:12][CH:11]1[C:15](OC)=[O:16].[Na].C(O)(=O)C>CO.O>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[N:1]1[C:15](=[O:16])[C:11]2[CH2:12][S:13][CH2:14][C:10]=2[NH:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 786452-HydrazinopyridineHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 5360545Sodium

Product 1

HCID 46244244HCID 46244244, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7 g (64.1 mmol) of 2-hydrazinopyridine and 10.3 g (64.1 mmol) of methyl 4-oxotetrahydrothiophene-3-carboxylate in 130 mL of MeOH is heated for 12 hours at 80° C. The medium is then concentrated under reduced pressure and the residue obtained is purified by chromatography on a column of silica gel, eluting with a DCM/MeOH gradient of from 0 to 10% MeOH. After concentrating under reduced pressure, 8.7 g (34.5 mmol) of hydrazone intermediate, in the form of a yellow powder, are isolated and are then added portionwise, at room temperature, to a solution of 0.8 g (34.5 mmol) of sodium in 46 mL of anhydrous MeOH. The reaction medium is stirred for 2 hours at room temperature, and the precipitate formed is then filtered off and washed successively with 10 mL of MeOH and 20 mL of pentane. The residue obtained is dissolved in 20 mL of water and 10 mL of acetic acid are added. The precipitate obtained is filtered off, washed with 10 mL of water, dried under vacuum and recrystallized from EtOH. 4.2 g of 2-pyridin-2-yl-1,2,4,6-tetrahydro-3H-thieno[3,4-c]pyrazol-3-one are obtained in the form of a whitish powder.

Workup

  1. concentrationThe medium is then concentrated under reduced pressure
  2. customthe residue obtained
  3. customis purified by chromatography on a column of silica gel
  4. washeluting with a DCM/MeOH gradient of from 0 to 10% MeOH
  5. customare isolated
  6. customthe precipitate formed
  7. filtrationis then filtered off
  8. washwashed successively with 10 mL of MeOH and 20 mL of pentane
  9. customThe residue obtained
  10. customThe precipitate obtained
  11. filtrationis filtered off
  12. washwashed with 10 mL of water
  13. customdried under vacuum
  14. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-cde196e023184a3f922a79fd2b40f1be
Source dataset
uspto-grants-2014_04
Patent number
US08697731B2

Reaction notes

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