1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-(2-hydroxy-3-pyrrolidin-1-yl-propyl)-acetamide

HRID 1359828Notes

Reaction equation

HRID 1359828 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]([CH2:30][C:31](O)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:56][CH2:57][CH:58]([OH:65])[CH2:59][N:60]1[CH2:64][CH2:63][CH2:62][CH2:61]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]([CH2:30][C:31]([NH:56][CH2:57][CH:58]([OH:65])[CH2:59][N:60]2[CH2:64][CH2:63][CH2:62][CH2:61]2)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 121749931-Amino-3-(pyrrolidin-1-yl)propan-2-olHCID 59077497HCID 59077497, compound

Product 1

HCID 590775822-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-(2-hydroxy-3-pyrrolidin-1-yl-propyl)-acetamideYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (300 mg, 0.578 mmol), HOBt (78 mg, 1 eq.) and EDAC (222 mg, 2 eq.) in DMF (1.5 mL) was stirred at rt for 30 mins. To the mixture was added 1-amino-3-pyrrolidin-1-yl-propan-2-ol (170 mg, 2 eq.) in DMF (1.5 mL). After stirring at rt for overnight, the reaction was concentrated and purified on a silica gel column to give 169 mg (45%) of the titled compound.

Workup

  1. stirringAfter stirring at rt for overnight
  2. concentrationthe reaction was concentrated
  3. custompurified on a silica gel column

Sources & evidence

ORD record
ord-0f57885c87554036890dae0a38b483ab
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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