1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-[3,5-dimethyl-4-((s)-3-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359833Notes

Reaction equation

HRID 1359833 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])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([C:30]([OH:32])=O)[C:25]=1[CH3:33])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:55]1([CH2:60][C@@H:61]2[CH2:66][CH2:65][CH2:64][NH:63][CH2:62]2)[CH2:59][CH2:58][CH2:57][CH2:56]1>CN(C=O)C>[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])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([C:30]([N:63]2[CH2:64][CH2:65][CH2:66][C@@H:61]([CH2:60][N:55]3[CH2:56][CH2:57][CH2:58][CH2:59]3)[CH2:62]2)=[O:32])[C:25]=1[CH3:33])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7183063(r)-3-Pyrrolidin-1-ylmethyl-piperidineHCID 590775075-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 590775645-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-[3,5-dimethyl-4-((s)-3-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (0.2 g, 0.4 mmol), HOBt (54 mg, 1 eq.), EDAC (77 mg, 1 eq.) in DMF (1.5 mL) was stirred at rt for 10 mins. To the mixture was added (R)-3-pyrrolidin-1-ylmethyl-piperidine (0.2 g, 3 eq.). After stirring at rt for over the weekend, the precipitate was collected by vacuum filtration, washed with water, sodium bicarbonate and water. The solid was then purified on a silica gel column to give 101 mg (46%) of the titled compound.

Workup

  1. stirringAfter stirring at rt for over the weekend
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with water, sodium bicarbonate and water
  4. customThe solid was then purified on a silica gel column

Sources & evidence

ORD record
ord-c30df57c4f5f4d2a9ae7d9eb74148cef
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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