1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(4-morpholinocarbonyl-1-butynyl)-3-hydroxy-3-(2-chlorophenyl)oxindole

HRID 1369092Notes

Reaction equation

HRID 1369092 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].[O:31]1[CH2:36][CH2:35][N:34]([C:37]([CH2:39][CH2:40][C:41]#[CH:42])=[O:38])[CH2:33][CH2:32]1>>[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:42]#[C:41][CH2:40][CH2:39][C:37]([N:34]3[CH2:35][CH2:36][O:31][CH2:32][CH2:33]3)=[O:38])[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 137650954-Morpholinocarbonyl-1-butyne

Product 1

HCID 111466041-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(4-morpholinocarbonyl-1-butynyl)-3-hydroxy-3-(2-chlorophenyl)oxindole

Procedure

The title compound (246 mg) was prepared from (+)-1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole (300 mg, 0.543 mmol) and 4-morpholinocarbonyl-1-butyne 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. The NMR spectra of the title compound exhibited the same as in Example 70. [α]D +58.3° (c=0.252, MeOH).

Workup

  1. customThe hydrochloride of the title compound was obtained

Sources & evidence

ORD record
ord-021c453bd0574486805fb7b71009be3c
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

Loading…