Trifluoroacetic acid → HCID 46899385, compound

HRID 1897837Notes

Reaction equation

HRID 1897837 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]1[N:13](C(OC(C)(C)C)=O)[C:12]2=[CH:21][S:22][C:23]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[S:31][CH:32]=[C:33]5[C:37]=4[NH:36][C:35](=[O:38])[N:34]5C(OC(C)(C)C)=O)=[CH:26][CH:25]=3)=[C:11]2[NH:10]1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[O:8]=[C:9]1[NH:13][C:12]2=[CH:21][S:22][C:23]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[S:31][CH:32]=[C:33]5[C:37]=4[NH:36][C:35](=[O:38])[NH:34]5)=[CH:26][CH:25]=3)=[C:11]2[NH:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67236826HCID 67236826, compound

Product 1

HCID 46899385HCID 46899385, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid in an amount of 40 equivalents relative to the obtained tert-butyl 4-[4-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)phenyl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate was added and a reaction was carried out at 25° C. for 3 hours. The resulting reaction liquid was dropped slowly to a saturated aqueous sodium carbonate solution to neutralize, thereby stopping the reaction. Ethyl acetate was added to the reaction liquid and stirred, and then an organic layer was taken and the solvent was distilled off. The residue was purified by silica gel column chromatography using an ethyl acetate/hexane solvent, so that 4-[4-(2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)phenyl]-2,3-dihydro-1H-thieno[3,4-d]imidazol-2-one was obtained. The yield based on the charged tert-butyl 4-[4-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)phenyl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate was 90%.

Workup

  1. customThe resulting reaction liquid
  2. customthe reaction
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b24739351c74fa6af844b435c176b13
Source dataset
uspto-grants-2013_08
Patent number
US08519150B2

Reaction notes

Loading…