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

HRID 1662611Notes

Reaction equation

HRID 1662611 reaction equation
[F:1][C@H:2]1[CH2:6][N:5]([C:7]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:16][C:17]([F:20])([F:19])[F:18])[CH:14]=3)[NH:9][C:8]2=[O:21])[C@H:4]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])[CH2:3]1.[CH3:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[C:39]([O:47][C:48]([F:51])([F:50])[F:49])[CH:38]=1>>[F:1][C@H:2]1[CH2:6][N:5]([C:7]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:16][C:17]([F:20])([F:19])[F:18])[CH:14]=3)[N:9]([S:43]([C:40]3[CH:41]=[CH:42][C:37]([O:36][CH3:35])=[CH:38][C:39]=3[O:47][C:48]([F:49])([F:50])[F:51])(=[O:45])=[O:44])[C:8]2=[O:21])[C@H:4]([C:30]([N:32]([CH3:33])[CH3:34])=[O:31])[CH2:3]1

Participants

3

Reactant 2

HCID 67429458(4R)-4-fluoro-1-[3-(2-methoxyphenyl)-2-oxo-5-(trifluoromethoxy)-2,3-dihydro-1H-indol-3-yl]-N,N-dimethyl-L-prolinamideHCID 866256844-Methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride

Product 1

HCID 59867834(4R)-4-fluoro-1-[3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-o xo-5-(trifluoromethoxy)-2,3-dihydro-1H-indol-3-yl]-N,N-dimethyl-L-prolinamideYield 51.7%

Procedure

With 200 mg of the compound obtained in Step 20-1 (Isomer B) and 133 mg of 4-methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride as starting material, 158 mg of the title compound (colorless amorphous) was obtained by a similar method to Example 2.

Sources & evidence

ORD record
ord-e744cb03e36142e29246d5d43a16cd15
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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