5-chloro-3-(2-methoxyphenyl)-3-[2-oxo-2-(4-pyridin-4-yl piperazin-1-yl)ethyl]-1,3-dihydro-2H-indol-2-one → 5-chloro-3-(2-methoxyphenyl)-1-{[2-methoxy-4-(trifluoromethoxy)phenyl]sulfonyl}-3-[2-oxo-2-(4-pyridin-4-yl piperazin-1-yl)ethyl]-1,3-dihydro-2H-indol-2-one

HRID 1662636Notes

Reaction equation

HRID 1662636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[CH2:12][C:13](=[O:26])[N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.[CH3:35][O:36][C:37]1[CH:42]=[C:41]([O:43][C:44]([F:47])([F:46])[F:45])[CH:40]=[CH:39][C:38]=1[S:48](Cl)(=[O:50])=[O:49]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:48]([C:38]1[CH:39]=[CH:40][C:41]([O:43][C:44]([F:45])([F:46])[F:47])=[CH:42][C:37]=1[O:36][CH3:35])(=[O:49])=[O:50])[C:6](=[O:11])[C:5]2([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[CH2:12][C:13](=[O:26])[N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 219254995-chloro-3-(2-methoxyphenyl)-3-[2-oxo-2-(4-pyridin-4-yl piperazin-1-yl)ethyl]-1,3-dihydro-2H-indol-2-oneHCID 717442152-Methoxy-4-(trifluoromethoxy)benzene-1-sulfonyl chloride

Product 1

HCID 119509235-chloro-3-(2-methoxyphenyl)-1-{[2-methoxy-4-(trifluoromethoxy)phenyl]sulfonyl}-3-[2-oxo-2-(4-pyridin-4-yl piperazin-1-yl)ethyl]-1,3-dihydro-2H-indol-2-oneYield 31.7%

Procedure

With 150 mg of 5-chloro-3-(2-methoxyphenyl)-3-[2-oxo-2-(4-pyridin-4-yl piperazin-1-yl)ethyl]-1,3-dihydro-2H-indol-2-one, which is the compound described in EXEMPLE 1 of Publication No. WO03/008407, and 100 mg of 2-methoxy-4-(trifluoromethoxy)benzene sulfonyl chloride as starting materials, 73 mg of the title compound (colorless amorphous) was obtained by a similar method to Example 1.

Sources & evidence

ORD record
ord-ecf0ee8e8b964a5a8cbb8e87b2357af2
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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