Acetic Acid → 5-[4-{3-(3-Methylimidazo[5,4-b]pyridin-2-yl)propoxy}-benzyl]thiazolidine-2,4-dione
Reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:47]=[CH:46][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[N:22](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:21]2=[O:45])=[CH:17][CH:16]=1.C(O)(=O)C>O>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:47]=[CH:46][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:45])=[CH:17][CH:16]=1Participants
4
Procedure
A procedure similar to that described in Example 12 was repeated, except that 240 mg of 5-[4-{3-(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)propoxy}benzyl]-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 35) and 10 ml of a 3:1 by volume mixture of acetic acid and water were used, to give the title compound as a crude product. This crude product was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of hexane and ethyl acetate in ratios ranging from 1:3 to 0:1 by volume as the eluent, to give 93 mg of the title compound, melting at 185-186° C.
Sources & evidence
- ORD record
- ord-598c5fb733104617bf60c32e5e5b396c
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977365
Reaction notes
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