(4R)-1-(3-benzyl-5-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-fluoro-N,N-dimethyl-L-prolinam ide → (4R)-1-(3-benzyl-5-chloro-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihy dro-1H-indol-3-yl)-4-fluoro-N,N-dimethyl-L-prolinamide

HRID 1662619Notes

Reaction equation

HRID 1662619 reaction equation
[CH2:1]([C:8]1([N:19]2[CH2:28][C@H:27]([F:29])[CH2:26][C@H:20]2[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[NH:10][C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[C:34]([O:42][C:43]([F:46])([F:45])[F:44])[CH:33]=1>>[CH2:1]([C:8]1([N:19]2[CH2:28][C@H:27]([F:29])[CH2:26][C@H:20]2[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[N:10]([S:38]([C:35]2[CH:36]=[CH:37][C:32]([O:31][CH3:30])=[CH:33][C:34]=2[O:42][C:43]([F:44])([F:45])[F:46])(=[O:40])=[O:39])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 67429949(4R)-1-(3-benzyl-5-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-fluoro-N,N-dimethyl-L-prolinam ideHCID 866256844-Methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride

Product 1

HCID 11951805(4R)-1-(3-benzyl-5-chloro-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihy dro-1H-indol-3-yl)-4-fluoro-N,N-dimethyl-L-prolinamideYield 47.8%

Procedure

With 87 mg of the compound obtained in Step 30-2 and of 74 mg 4-methoxy-2-(trifluoromethoxy)benzene sulfonyl chloride as starting materials, 67 mg of the title compound (colorless solid) was obtained by a similar method to Example 2.

Sources & evidence

ORD record
ord-0e880950c86141e78cb63f4c5ca9d04a
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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