1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole → (+)-1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(3-methanesulfonylamino-1-propynyl)-3-hydroxy-3-(2-chlorophenyl)oxindole

HRID 1369093Notes

Reaction equation

HRID 1369093 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].[CH3:31][S:32]([NH:35][CH2:36][C:37]#[CH:38])(=[O:34])=[O:33]>>[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:38]#[C:37][CH2:36][NH:35][S:32]([CH3:31])(=[O:34])=[O:33])[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 14025440N-(Prop-2-yn-1-yl)methanesulfonamide

Product 1

HCID 18518564(+)-1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(3-methanesulfonylamino-1-propynyl)-3-hydroxy-3-(2-chlorophenyl)oxindole

Procedure

The title compound (270 mg) was prepared from (+)-1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole of Example 72(1) (347 mg, 0.628 mmol) and 1-methanesulfonylamino-2-propyne 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-949d585f24d2438eb8230e78776538e9
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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