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

HRID 1599245Notes

Reaction equation

HRID 1599245 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-0f57f82ce8b54d94ac0647040d0420e8
Source dataset
uspto-grants-1998_04
Patent number
US05739345

Reaction notes

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