4-Morpholinocarbonyl-1-butyne → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(4-morpholinocarbonyl-1-butynyl)-3-hydroxy-3-(phenyl)oxindole

HRID 1369121Notes

Reaction equation

HRID 1369121 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[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:26])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]1=[O:27])[CH3:2].[O:30]1[CH2:35][CH2:34][N:33]([C:36]([CH2:38][CH2:39][C:40]#[CH:41])=[O:37])[CH2:32][CH2:31]1>>[CH2:1]([N:3]([CH2:28][CH3:29])[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:41]#[C:40][CH2:39][CH2:38][C:36]([N:33]3[CH2:34][CH2:35][O:30][CH2:31][CH2:32]3)=[O:37])[CH:13]=2)[C:8]([OH:26])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]1=[O:27])[CH3:2]

Participants

3

Reactant 2

HCID 137650954-Morpholinocarbonyl-1-butyneHCID 185186121-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(phenyl)oxindole

Product 1

HCID 185186451-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(4-morpholinocarbonyl-1-butynyl)-3-hydroxy-3-(phenyl)oxindoleYield 106%

Procedure

The title compound (65.2 mg, 88%) was prepared from 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(phenyl)oxindole (57.2 mg) and 4-morpholinocarbonyl-1-butyne (31.1 mg) by the procedure similar to that described in Reference Example 21. The compound obtained was further purified by reverse phase HPLC with water-acetonitrile-trifluoroacetic acid.

Workup

  1. customThe compound obtained
  2. customwas further purified by reverse phase HPLC with water-acetonitrile-trifluoroacetic acid

Sources & evidence

ORD record
ord-1f79933e9a2c4693b8b42bebe055deec
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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