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

HRID 1662631Notes

Reaction equation

HRID 1662631 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:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])[CH2:12][C:13](=[O:25])[N:14]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)[CH2:16][CH2:15]1.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[C:38]([O:46][C:47]([F:50])([F:49])[F:48])[CH:37]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:42]([C:39]1[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][C:38]=1[O:46][C:47]([F:48])([F:49])[F:50])(=[O:44])=[O:43])[C:6](=[O:11])[C:5]2([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])[CH2:12][C:13](=[O:25])[N:14]1[CH2:15][CH2:16][N:17]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 674300515-chloro-3-(2-methoxyphenyl)-3-{2-oxo-2-[4-(1,3-thiazol-2-yl)piperazin-1-yl]ethyl}-1,3-dihydro-2H-indol-2-oneHCID 866256844-Methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride

Product 1

HCID 119510965-chloro-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-3-{2-oxo-2-[4-(1,3-thiazol-2-yl)piperazin-1-yl]ethyl}-1,3-dihydro-2H-indol-2-oneYield 89.3%

Procedure

With 300 mg of the compound obtained in Step 46-1 and 200 mg of 4-methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride as starting materials, 409 mg of the title compound (yellow amorphous) was obtained by a similar method to Example 2.

Sources & evidence

ORD record
ord-612c011bf1b5407389183f0e70ca6420
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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