Dimethylamine → 5-Butylidene-3-[4-(3-dimethylaminomethylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357151Notes

Reaction equation

[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH:6](=[C:10]1[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]2[N:26]3[CH:27]=[CH:28][N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9].[OH-].[Na+]>C(O)(=O)C>[CH:6](=[C:10]1[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]2[N:26]3[C:27]([CH2:3][N:4]([CH3:1])[CH3:5])=[CH:28][N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.27 ml (3.6 mmol) of formalin and 0.33 g (3.6 mmol) of a 50% aqueous dimethylamine solution in 20 ml of acetic acid, a solution of 1.13 g (3.0 mmol) of 5-butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione in 5 ml of acetic acid was added at 0° C., followed by stirring at 80° C. for 90 minutes. After cooling, the reaction mixture was poured into 50 ml of 50% aqueous sodium hydroxide under ice cooling conditions. The mixture was extracted with chloroform and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=25/1) to yield 0.43 g (33.3%, yellow oily substance) of the desired product.

Workup

temperatureAfter cooling
extractionThe mixture was extracted with chloroform
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent, chloroform/methanol=25/1)

Sources & evidence

ORD record: ord-fad4aecc3c424606b99c8356a387d768
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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