Hydrogen chloride-ethyl acetate → 5-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione dihydrochloride

HRID 357106Notes

Reaction equation

HRID 357106 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=[C:10]2[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[C:22]4[N:23]([CH:27]=[CH:28][N:29]=4)[CH:24]=[CH:25][CH:26]=3)[C:11]2=[O:30])[CH:2]=1.[ClH:31].C(OCC)(=O)C>CO>[ClH:31].[ClH:31].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=[C:10]2[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[C:22]4[N:23]([CH:27]=[CH:28][N:29]=4)[CH:24]=[CH:25][CH:26]=3)[C:11]2=[O:30])[CH:2]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 572830815-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Product 1

HCID 734729205-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol solution of 0.49 g (1.2 mmol) of 5-[3-(3-pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione, 0.5 ml of 4N hydrochloric acid-ethyl acetate was added, followed by stirring, after which the solvent was distilled off, to yield 0.44 g (74.2%, white oily substance) of the desired product.

Workup

  1. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-9d384d3192c74430bed072d080bc95f3
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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