1-(3-(Methylsulfonyl)propyl)piperazine → rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-1'-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-1H-spiro[indole-3,3'-pyrrolidin]-2-one

HRID 2065426Notes

Reaction equation

HRID 2065426 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C:10]3([CH:14]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][N:12]([C:20](Cl)=[O:21])[CH:11]3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[F:30])[C:5]2=[CH:4][CH:3]=1.[CH3:32][S:33]([CH2:36][CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)(=[O:35])=[O:34]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C:10]3([CH:14]([CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:13][N:12]([C:20]([N:42]4[CH2:41][CH2:40][N:39]([CH2:38][CH2:37][CH2:36][S:33]([CH3:32])(=[O:34])=[O:35])[CH2:44][CH2:43]4)=[O:21])[CH:11]3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[F:30])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 498534781-(3-(Methylsulfonyl)propyl)piperazineHCID 76776161rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carbonyl chloride

Product 1

HCID 67337303rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-1'-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-1H-spiro[indole-3,3'-pyrrolidin]-2-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner similar to the method described in Example 9, rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carbonyl chloride prepared in Example 8 (53 mg, 0.11 mmol) was reacted with 1-(3-methanesulfonyl-propyl)-piperazine (34 mg, 0.14 mmol) and triethylamine to give rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-1′-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-1H-spiro[indole-3,3′-pyrrolidin]-2-one as a white solid (Yield, 61 mg, 79%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-8720bca0d9f043cba9f5ab9b8d6d7745
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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