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

HRID 1662621Notes

Reaction equation

HRID 1662621 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]=[C:37]([O:39][C:40]([F:43])([F:42])[F:41])[CH:36]=[CH:35][C:34]=1[S:44](Cl)(=[O:46])=[O:45]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:44]([C:34]1[CH:35]=[CH:36][C:37]([O:39][C:40]([F:41])([F:42])[F:43])=[CH:38][C:33]=1[O:32][CH3:31])(=[O:45])=[O:46])[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 717442152-Methoxy-4-(trifluoromethoxy)benzene-1-sulfonyl chloride

Product 1

HCID 11951803(2S)-1-(5-chloro-3-(2-methoxyphenyl)-1-{[2-methoxy-4-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethylpiperidine-2-carboxamideYield 44.7%

Procedure

With 303 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 the brochure Publication No. WO01/98295 and 245 mg of 2-methoxy-4-(trifluoromethoxy)benzene sulfonyl chloride as starting materials, 216 mg of the title compound (colorless amorphous) was obtained by a similar method to Example 1.

Workup

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

Sources & evidence

ORD record
ord-195b9130697a425fa3526fc349e5b90c
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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