1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole → (+)-1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-[4-(N-hydroxyethylcarbamoyl)-1-butynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole

HRID 1369094Notes

Reaction equation

HRID 1369094 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12](I)[CH:13]=2)[C:8]([OH:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[C:7]1=[O:28])[CH3:2].[OH:31][CH2:32][CH2:33][NH:34][C:35](=[O:40])[CH2:36][CH2:37][C:38]#[CH:39]>>[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12]([C:39]#[C:38][CH2:37][CH2:36][C:35](=[O:40])[NH:34][CH2:33][CH2:32][OH:31])[CH:13]=2)[C:8]([OH:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[C:7]1=[O:28])[CH3:2]

Participants

3

Reactant 2

HCID 129902161-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindoleHCID 54114534N-hydroxyethyl-4-pentynamide

Product 1

HCID 18518604(+)-1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-[4-(N-hydroxyethylcarbamoyl)-1-butynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole

Procedure

The title compound (740 mg) was prepared from (+)-1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole of Example 72(1) (102 mg, 0.185 mmol) and N-hydroxyethyl-4-pentynamide by the procedure similar to that described in Reference Example 21. The hydrochloride of the title compound was obtained by treating with 4 N HCl in dioxane followed by concentration to dryness.

Workup

  1. customThe hydrochloride of the title compound was obtained

Sources & evidence

ORD record
ord-2a18e61a7d534a278dc7c40881974985
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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