1,2,5-thiadiazole-3,4-diamine → HCID 59457653, compound

HRID 1710684Notes

Reaction equation

HRID 1710684 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)[CH:5]=[CH:6][CH:7]=1.[S:18]1[N:22]=[C:21]([NH2:23])[C:20]([NH2:24])=[N:19]1>CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:24][C:20]3=[N:19][S:18][N:22]=[C:21]3[N:23]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 109204841,2,5-thiadiazole-3,4-diamineHCID 53415635HCID 53415635, compound

Product 1

HCID 59457653HCID 59457653, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(3-fluorophenyl)-2-pyridin-4-ylethane-1,2-dione (1.5 g, 6.5 mmol) and 1,2,5-thiadiazole-3,4-diamine (1.1 g, 9.8 mmol) in AcOH (30 mL) was stirred and heated at reflux for 1 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and a solution of NaHCO3 4%. The organic phase was dried (MgSO4) and evaporated to dryness to give the title compound as a dark oil (1.7 g, 82%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ecf287d6a46b471da6354b583341fa9a
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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