Trifluoroacetic acid → HCID 58399754, compound

HRID 1897838Notes

Reaction equation

HRID 1897838 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:21]2[CH:20]=[CH:19][C:18]([C:22]3[S:23][CH:24]=[C:25]4[C:29]=3[NH:28][C:27](=[O:30])[N:26]4C(OC(C)(C)C)=O)=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([C:38]1[S:39][CH:40]=[C:41]3[C:45]=1[NH:44][C:43](=[O:46])[N:42]3C(OC(C)(C)C)=O)[CH:14]=2.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH3:8][N:9]1[C:21]2[CH:20]=[CH:19][C:18]([C:22]3[S:23][CH:24]=[C:25]4[C:29]=3[NH:28][C:27](=[O:30])[NH:26]4)=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([C:38]1[S:39][CH:40]=[C:41]3[C:45]=1[NH:44][C:43](=[O:46])[NH:42]3)[CH:14]=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67237662HCID 67237662, compound

Product 1

HCID 58399754HCID 58399754, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid in an amount of 40 equivalents was added to the obtained tert-butyl 4-[9-methyl-6-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)-9H-carbazol-3-yl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate 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-[9-methyl-6-(2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-9H-carbazol-3-yl]-2,3-dihydro-1H-thieno[3,4-d]imidazol-2-one was obtained. The yield based on the charged tert-butyl 4-[9-methyl-6-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)-9H-carbazol 3-yl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxy late 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-6b2d46dc6b5243f5bc2c103aaa54d024
Source dataset
uspto-grants-2013_08
Patent number
US08519150B2

Reaction notes

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