Ethanol → HCID 10670288, compound

HRID 1601783Notes

Reaction equation

HRID 1601783 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.O=[CH:16][CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:21][CH:20]=1.II.C(O)C>COCCOC.C(O)(=O)C>[C:9]1([N:8]2[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[N:1]=[C:16]2[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:31][CH:32]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 807IodineHCID 106790912-N-phenylpyridine-2,3-diamineHCID 108492775-[4-(2-Oxoethoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 10670288HCID 10670288, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A procedure similar to that described in Example 18 was repeated, except that 2.78 g of 3-amino-2-phenylaminopyridine (prepared as described in Preparation 84), 3.98 g of 5-[4-(2-oxoethoxy)benzyl)thiazolidine-2,4-dione (prepared as described in Preparation 47), 4.9 g of iodine, 6 ml of ethanol, 6 ml of acetic acid and 50 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 a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 400 mg of the title compound, melting at 88-91° C.

Workup

  1. customthe resulting crude product was purified by column chromatography through silica gel
  2. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-02e499ad0dda458b987d42119b5f1f1f
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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