Piperidine → HCID 59077747, compound

HRID 1359881Notes

Reaction equation

HRID 1359881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16]2)(=[O:12])=[O:11].[CH3:23][C:24]1[C:28]([CH2:29][CH2:30][C:31](=[O:43])[N:32]2[CH2:36][CH2:35][CH2:34][C@H:33]2[CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[C:27]([CH3:44])[NH:26][C:25]=1[CH:45]=O.N1CCCCC1>C(O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:45]\[C:25]1[NH:26][C:27]([CH3:44])=[C:28]([CH2:29][CH2:30][C:31](=[O:43])[N:32]2[CH2:36][CH2:35][CH2:34][C@H:33]2[CH2:37][N:38]2[CH2:39][CH2:40][CH2:41][CH2:42]2)[C:24]=1[CH3:23])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 181797685-(2,6-Dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-oneHCID 88094401HCID 88094401, compound

Product 1

HCID 59077747HCID 59077747, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2,6-dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one (100 mg, 0.28 mmol), 3,5-dimethyl-4-[3-oxo-3-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-propyl]-1H-pyrrole-2-carbaldehyde (1.7 eq.) and piperidine (1.5 eq.) in ethanol (2 mL) was stirred at rt for 96 hours. The reaction was concentrated and purified on a silica gel column to give the titled compound as a pale orange solid.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified on a silica gel column

Sources & evidence

ORD record
ord-a8a60c8c2b4f43c6beaddbe5f3587119
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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