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

HRID 357141Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].N12CCCNC1CCCC=C2.O>CN(C)C=O>[N:17]1[CH:16]=[CH:15][N:14]2[C:9]([S:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:20]3[C:21](=[O:23])[CH2:22][S:18][C:19]3=[O:24])(=[O:8])=[O:7])=[CH:10][CH:11]=[CH:12][C:13]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.27 g (1.0 mmol) of 5-(4-chlorobutylsulfonyl)imidazo[1,2-a]pyridine and 0.177 g (1.0 mmol) of thiazolidine-2,4-dione in 7 ml of N,N-dimethylformamide, 0.15 ml (1.0 mmol) of 1,8-diazabicyclo[5.4.0]-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 0.22 g (62.2%, 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-6bf2f688afb946ceb7d2131c8f22c8fa
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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