HCID 20094134, compound → HCID 20094163, compound

HRID 273789Notes

Reaction equation

HRID 273789 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:12](=[O:13])[C:11]2[S:14][CH:15]=[CH:16][C:10]=2[N:9]2[CH:17]=[N:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:8]2[CH2:7]1>FC(F)(F)C(O)=O>[O:13]=[C:12]1[C:11]2[S:14][CH:15]=[CH:16][C:10]=2[N:9]2[CH:17]=[N:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:8]2[CH2:7][NH:6]1

Participants

3

Reactant 1

HCID 20094134HCID 20094134, compound

Product 1

HCID 20094163HCID 20094163, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3. 3.6 g of ethyl 5-(2,4-dimethoxybenzyl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate are heated to reflux in 12.5 ml of trifluoroacetic acid for 2 h. The reaction mixture is then evaporated in a vacuum and the residue is partitioned between dichloromethane and water. The mixture is neutralized by the addition of sodium hydrogen carbonate. The emulsion obtained is filtered through Dicalite and the Dicalite is rinsed with dichloromethane. The phases of the filtrate are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried and evaporated in a vacuum. The residue is boiled in ethyl acetate; the crystals obtained are filtered off. There are obtained 1.6 g of ethyl 5,6-dihydro-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate of m.p. 263°-264° C.

Workup

  1. customThe reaction mixture is then evaporated in a vacuum
  2. customthe residue is partitioned between dichloromethane and water
  3. additionThe mixture is neutralized by the addition of sodium hydrogen carbonate
  4. customThe emulsion obtained
  5. filtrationis filtered through Dicalite
  6. washthe Dicalite is rinsed with dichloromethane
  7. customThe phases of the filtrate are separated
  8. extractionthe aqueous phase is extracted with dichloromethane
  9. customThe combined organic phases are dried
  10. customevaporated in a vacuum
  11. customthe crystals obtained
  12. filtrationare filtered off

Sources & evidence

ORD record
ord-bacde0d17eb2479aa903030e83ad537c
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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