Water → 3-[4-(Imidazo[1,2-a]pyridin-5-ylsulfinyl)butyl]thiazolidine-2,4-dione

HRID 357137Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1)=[O:7].[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[N:16]1[CH:15]=[CH:14][N:13]2[C:8]([S:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:19]3[C:20](=[O:22])[CH2:21][S:17][C:18]3=[O:23])=[O:7])=[CH:9][CH:10]=[CH:11][C:12]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.51 g (2.0 mmol) of 5-(4-chlorobutylsulfinyl)imidazo[1,2-a]pyridine and 0.355 g (2.0 mmol) of thiazolidine-2,4-dione in 10 ml of N,N-dimethylformamide, 0.30 ml (2.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by heating at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform→chloroform/methanol=50/1) to yield 0.33 g (49.0%, light yellow oily substance) of the desired product.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washwashed with water
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent, chloroform→chloroform/methanol=50/1)

Sources & evidence

ORD record: ord-cc3e941c7e3f489cb1ab78c7c7ec8ee8
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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