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

HRID 1738186Notes

Reaction equation

HRID 1738186 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH3:48])[C:11]([CH2:13][O:14][C:15]3[CH:47]=[CH:46][C:18]([CH2:19][CH:20]4[S:24][C:23](=[O:25])[N:22](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[C:21]4=[O:45])=[CH:17][CH:16]=3)=[N:12][C:7]2=[CH:6][CH:5]=1)[CH3:2].C(O)(=O)C>O>[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH3:48])[C:11]([CH2:13][O:14][C:15]3[CH:47]=[CH:46][C:18]([CH2:19][CH:20]4[S:24][C:23](=[O:25])[NH:22][C:21]4=[O:45])=[CH:17][CH:16]=3)=[N:12][C:7]2=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 105562575-{4-(5-Ethoxy-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 105496165-{4-(5-Ethoxy-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dioneYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Example 12 was repeated, except that 2.75 g of 5-{4-(5-ethoxy-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 99) were treated with 24 ml of a 3:1 by volume mixture of acetic acid and water. After working up the product as described in Example 12, the resulting crude product was crystallized by trituration with ethyl acetate, to give 1.57 g of the title compound, melting at 245-246° C.

Workup

  1. customthe resulting crude product was crystallized by trituration with ethyl acetate

Sources & evidence

ORD record
ord-74820c1ab417450495798191d9fbda29
Source dataset
uspto-grants-1999_10
Patent number
US05962470

Reaction notes

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