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

HRID 357089

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.[CH3:16][N:17]([CH:19]=[C:20]1[S:24][C:23](=[O:25])[NH:22][C:21]1=[O:26])[CH3:18].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[CH3:18][N:17]([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])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 241 mg (1.0 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 173 mg (1.0 mmol) of 5-(dimethylamino)methylene-thiazolidine-2,4-dione in 10 ml of N,N-dimethylformamide, 0.15 ml (1.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by stirring at 80°C. for 3 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, n-hexane/ethyl acetate=1/4→ethyl acetate→chloroform/ethanol=10/1) to yield 310 mg (82.3%, yellow 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, n-hexane/ethyl acetate=1/4→ethyl acetate→chloroform/ethanol=10/1)

Sources & evidence

ORD record: ord-ff75dc621b7d464ebb668b21b1fa1dfb
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Linked notes

Loading…