Ethanol → 5-{4-[2-(3-Methylimidazo[5,4-b]pyridin-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione

HRID 1601788Notes

Reaction equation

HRID 1601788 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.O=[CH:11][CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1.C(O)C.II>COCCOC.C(O)(=O)C>[CH3:9][N:8]1[C:3]2=[N:4][CH:5]=[CH:6][CH:7]=[C:2]2[N:1]=[C:11]1[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 807IodineHCID 104929285-[4-(3-Oxopropoxy)benzyl]thiazolidine-2,4-dioneHCID 123436692-N-methylpyridine-2,3-diamine

Product 1

HCID 105719565-{4-[2-(3-Methylimidazo[5,4-b]pyridin-2-yl)ethoxy]benzyl}thiazolidine-2,4-dioneYield 3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A procedure similar to that described in Example 18 was repeated, except that 0.94 g of 3-amino-2-methylaminopyridine (prepared as described in Preparation 105), 2.10 g of 5-[4-(3-oxopropoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Preparation 107), 6 ml of ethanol, 3 ml of acetic acid, 2.32 g of iodine and 30 ml of 1,2-dimethoxyethane were used. After working up the product as described in Example 18, the resulting crude product was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 85 mg of the title compound, melting at 96-100° C.

Workup

  1. customthe resulting crude product was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-fb3b8004977141cb89a4fc7cadc17141
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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