Water → 5-(Ethylthiomethylene)-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357157Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[CH2:16]([S:18][CH:19]=[C:20]1[S:24][C:23](=[O:25])[NH:22][C:21]1=[O:26])[CH3:17].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[CH2:16]([S:18][CH:19]=[C:20]1[S:24][C:23](=[O:25])[N:22]([CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[C:21]1=[O:26])[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 601 mg (2.5 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 473 mg (2.5 mmol) of 5-(ethylthiomethylene)thiazolidine-2,4-dione in 5 ml of N,N-dimethylformamide, 0.37 ml (2.5 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by stirring at 80° C. for 16 hours. After the reaction mixture was cooled, water was added; the mixture was extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/4→ethyl acetate) to yield 0.76 g (77.2%, light orange oily substance) of the desired product.

Workup

temperatureAfter the reaction mixture was cooled
extractionthe mixture was extracted with ethyl acetate
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/4→ethyl acetate)

Sources & evidence

ORD record: ord-8fffcea8d6a945fbb9ae7f74bf61b720
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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