Acetoxyacetyl chloride → N-[6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-2-hydroxyacetamide

HRID 8818Notes

Reaction equation

HRID 8818 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:26].C([O:36][CH2:37][C:38](Cl)=[O:39])(=O)C>>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:7]1[N:6]=[C:5]2[O:4][C:3]([C:25]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:26])=[C:2]([NH:1][C:37](=[O:36])[CH2:38][OH:39])[C:10]2=[CH:9][C:8]=1[C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 21984803[3-Amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

Product 1

HCID 21984896N-[6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-2-hydroxyacetamide

Procedure

Using the general acylating procedure described in Example 18, the product of Example 157 was reacted with acetoxyacetyl chloride and then subjected to the general ester hydrolysis procedure described in Example 25 to afford the title compound. HPLC/MS: 518.0 (M+1), 520.0 (M+3); Rt=3.52 min.

Sources & evidence

ORD record
ord-c381bed665bb4627a586bfbdff44fdf8
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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