(2S)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-N,N-dimethylpiperidine-2-carboxamide → (2S)-1-(5-chloro-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethylpiperidine-2-carboxamide

HRID 1662620Notes

Reaction equation

HRID 1662620 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([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[C:35]([O:43][C:44]([F:47])([F:46])[F:45])[CH:34]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:39]([C:36]1[CH:37]=[CH:38][C:33]([O:32][CH3:31])=[CH:34][C:35]=1[O:43][C:44]([F:45])([F:46])[F:47])(=[O:41])=[O:40])[C:6](=[O:11])[C:5]2([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[C:26]([N:28]([CH3:29])[CH3:30])=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19]

Participants

3

Reactant 2

HCID 67429052(2S)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-N,N-dimethylpiperidine-2-carboxamideHCID 866256844-Methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride

Product 1

HCID 11951804(2S)-1-(5-chloro-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethylpiperidine-2-carboxamideYield 40.4%

Procedure

With 500 mg of (2S)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-N,N-dimethylpiperidine-2-carboxamide, which is the compound described in Preparation 3.49 (Isomer B) of Publication No. WO01/98295 and 374 mg of 4-methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride as starting materials, 322 mg of the title compound (colorless amorphous) was obtained by a similar method to Example 2.

Workup

  1. customdescribed in Preparation 3.49 (Isomer B) of Publication No

Sources & evidence

ORD record
ord-c8cf312d549f4881be485e11017456a2
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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