Piperidine → 3-[1-{3,5-Dimethyl-4-[2-oxo-2-((s)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-5-phenylmethanesulfonyl-1,3-dihydro-indol-2-one

HRID 1359777Notes

Reaction equation

HRID 1359777 reaction equation
[C:1]1([CH2:7][S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH2:14]3)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[C:26]([CH2:27][C:28](=[O:40])[N:29]2[CH2:33][CH2:32][CH2:31][C@H:30]2[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[C:25]([CH3:41])[NH:24][C:23]=1[CH:42]=O.N1CCCCC1>C(O)C>[CH3:21][C:22]1[C:26]([CH2:27][C:28](=[O:40])[N:29]2[CH2:33][CH2:32][CH2:31][C@H:30]2[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[C:25]([CH3:41])[NH:24][C:23]=1/[CH:42]=[C:14]1\[C:15](=[O:20])[NH:16][C:17]2[C:13]\1=[CH:12][C:11]([S:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:10])=[O:9])=[CH:19][CH:18]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 21139221HCID 21139221, compoundHCID 880943273,5-Dimethyl-4-[2-oxo-2-((s)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-ethyl]-1h-pyrrole-2-carbaldehyde

Product 1

HCID 590774823-[1-{3,5-Dimethyl-4-[2-oxo-2-((s)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-5-phenylmethanesulfonyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-phenylmethanesulfonyl-1,3-dihydro-indol-2-one (100 mg, 0.35 mmol), 3,5-dimethyl-4-[2-oxo-2-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-ethyl]-1H-pyrrole-2-carbaldehyde (110 mg, 1 eq.) and piperidine (0.5 eq.) in ethanol (2 mL) was stirred at rt for 48 hours. The reaction was concentrated, triturated with methanol, filtered and washed wit DCM to give the titled compound as a pale orange solid.

Workup

  1. concentrationThe reaction was concentrated
  2. customtriturated with methanol
  3. filtrationfiltered
  4. washwashed wit DCM

Sources & evidence

ORD record
ord-62c45ba6a11345dfb83cc31995f68e80
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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