Acetic Acid → 5-{4-(5-Chloro-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dione

HRID 356249Notes

Reaction equation

HRID 356249 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:46])[C:9]([CH2:11][O:12][C:13]3[CH:45]=[CH:44][C:16]([CH2:17][CH:18]4[S:22][C:21](=[O:23])[N:20](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[C:19]4=[O:43])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.C(O)(=O)C>O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:46])[C:9]([CH2:11][O:12][C:13]3[CH:45]=[CH:44][C:16]([CH2:17][CH:18]4[S:22][C:21](=[O:23])[NH:20][C:19]4=[O:43])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 105800365-{4-(5-Chloro-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 107873215-{4-(5-Chloro-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Example 12 was repeated, except that 1.16 g of 5-{4-(5-chloro-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 45) and 16 ml of a 3:1 by volume mixture of acetic acid and water were used, to give the title compound as a crude product. The product was crystallized by trituration with ethyl acetate, to give 0.38 g of the title compound, melting at 222°-223° C.

Sources & evidence

ORD record
ord-0c14f8bcff7944398e6dcf8d51e642d3
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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