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

HRID 356260Notes

Reaction equation

HRID 356260 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]2[N:11]([CH3:49])[C:12]([CH2:14][O:15][C:16]3[CH:48]=[CH:47][C:19]([CH2:20][CH:21]4[S:25][C:24](=[O:26])[N:23](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[C:22]4=[O:46])=[CH:18][CH:17]=3)=[N:13][C:8]2=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(O)(=O)C>O>[CH:1]([O:4][C:5]1[N:10]=[C:9]2[N:11]([CH3:49])[C:12]([CH2:14][O:15][C:16]3[CH:48]=[CH:47][C:19]([CH2:20][CH:21]4[S:25][C:24](=[O:26])[NH:23][C:22]4=[O:46])=[CH:18][CH:17]=3)=[N:13][C:8]2=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 107945465-{4-(5-Isopropoxy-3-methylimidazo(5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 108361855-{4-(5-Isopropoxy-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dioneYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Example 12 was repeated, except that 0.78 g of 5-{4-(5-isopropoxy-3-methylimidazo(5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 103) was treated with 12 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 0.40 g of the title compound, melting at 210°-212° C.

Workup

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

Sources & evidence

ORD record
ord-cabd3a7828a94d8ea6d5cf70c13f19d3
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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