1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydroxy-N,N-dimeth yl-L-prolinamide → 1-(5-chloro-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-3,4-dihydroxy-N,N-dimethyl-L-prolinamide

HRID 1662610Notes

Reaction equation

HRID 1662610 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[CH2:29][CH:28]([OH:30])[CH:27]([OH:31])[C@H:21]1[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[C:36]([O:44][C:45]([F:48])([F:47])[F:46])[CH:35]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:40]([C:37]1[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][C:36]=1[O:44][C:45]([F:46])([F:47])[F:48])(=[O:42])=[O:41])[C:6](=[O:11])[C:5]2([N:20]1[CH2:29][CH:28]([OH:30])[CH:27]([OH:31])[C@H:21]1[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19]

Participants

3

Reactant 2

HCID 674280011-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydroxy-N,N-dimeth yl-L-prolinamideHCID 866256844-Methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride

Product 1

HCID 598677711-(5-chloro-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-3,4-dihydroxy-N,N-dimethyl-L-prolinamideYield 52.7%

Procedure

With 300 mg of the compound obtained in Step 19-7 and 215 mg of 4-methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride as starting material, 248 mg of the title compound (colorless amorphous) was obtained by a similar method to Example 2.

Sources & evidence

ORD record
ord-4988a15719a444beae9b0d3afea5081d
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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