5-{4-(Imidazo[1,2-a]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione → 5-{4-(Imidazo[1,2-a]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dione
Reaction equation
[N:1]1[C:2]([CH2:10][O:11][C:12]2[CH:44]=[CH:43][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:18]3=[O:42])=[CH:14][CH:13]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12>FC(F)(F)C(O)=O>[N:1]1[C:2]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:42])=[CH:43][CH:44]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12Participants
3
Procedure
A procedure similar to that described in Example 1 was repeated, except that 3.0 g of 5-{4-(imidazo[1,2-a]pyridin-2-ylmethoxy) benzyl} -3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 21) were reacted with 30 ml of trifluoroacetic acid for 1 hour. At the end of this time, the reaction mixture was freed from trifluoroacetic acid by distillation under reduced pressure. An aqueous solution of potassium carbonate and ethyl acetate were added to the residue, and the resulting precipitated insoluble material was collected by filtration, dried over anhydrous sodium sulfate and recrystallized from ethanol, to give 0.8 g of the title compound, melting at 197-202° C.
Workup
- distillationAt the end of this time, the reaction mixture was freed from trifluoroacetic acid by distillation under reduced pressure
- additionAn aqueous solution of potassium carbonate and ethyl acetate were added to the residue
- customthe resulting precipitated insoluble material
- filtrationwas collected by filtration
- dry with materialdried over anhydrous sodium sulfate
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-19150eec487849aaa44d533d19f0e2cd
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977365
Reaction notes
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