Thiazolidinedione → 3-[4-(2-Methylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357021Notes

Reaction equation

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

Participants

Reactant 3

HCID 5437Thiazolidinedione

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

HCID 189366625-(4-Chlorobutylthio)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 189368353-[4-(2-Methylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Procedure

Using 0.76 g (3.0 mmol) of 5-(4-chlorobutylthio)-2-methylimidazo[1,2-a]pyridine, 0.35 g (3.0 mmol) of thiazolidine-2,4-dione and 0.45 ml (3.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene, the same procedure as in Reference Example 2 was followed, to yield 0.78 g (77.7%, light yellow oily substance) of the desired product.

Sources & evidence

ORD record: ord-0fcb5d6fc33a4613981ea0a04354f989
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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