Ethanol → HCID 10696037, compound

HRID 356251Notes

Reaction equation

HRID 356251 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.O=[CH:18][CH2:19][O:20][C:21]1[CH:34]=[CH:33][C:24]([CH2:25][CH:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:23][CH:22]=1.C(O)C.II>COCCOC.C(O)(=O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]2[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[N:1]=[C:18]2[CH2:19][O:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])=[CH:33][CH:34]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 807IodineHCID 108492775-[4-(2-Oxoethoxy)benzyl]thiazolidine-2,4-dioneHCID 149530053-Amino-2-(4-chlorobenzyl)aminopyridine

Product 1

HCID 10696037HCID 10696037, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A procedure similar to that described in Example 18 was repeated, except that 1.20 g of 3-amino-2-(4-chloro- benzyl)aminopyridine (prepared as descried in Preparation 53), 1.36 g of 5-[4-(2-oxoethoxy)benzyl]-thiazolidine-2,4-dione (prepared as described in Preparation 47), 3 ml of ethanol, 3 ml of acetic acid, 1.69 g of iodine and 25 ml of 1,2-dimethoxyethane were used, to give the title compound as a crude product. This crude product was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of hexane and ethyl acetate in ratios ranging from 1:1 to 1:2 by volume as the eluent, to give 0.40 g of the title compound, melting at 211°-213° C.

Sources & evidence

ORD record
ord-938c51ba08dc4a4984c7d8fc96f6195f
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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