1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077637, compound

HRID 1359846Notes

Reaction equation

HRID 1359846 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.[CH:56]1([NH:59][CH2:60][C@@H:61]2[CH2:66][CH2:65][CH2:64][NH:63][CH2:62]2)[CH2:58][CH2:57]1>CN(C=O)C>[CH:56]1([NH:59][CH2:60][C@@H:61]2[CH2:66][CH2:65][CH2:64][N:63]([C:31](=[O:32])[CH2:30][C:26]3[C:25]([CH3:34])=[C:24](/[CH:23]=[C:16]4\[C:17](=[O:22])[NH:18][C:19]5[C:15]\4=[CH:14][C:13]([S:10]([CH2:9][C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])(=[O:11])=[O:12])=[CH:21][CH:20]=5)[NH:28][C:27]=3[CH3:29])[CH2:62]2)[CH2:58][CH2:57]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59077497HCID 59077497, compoundHCID 69869732HCID 69869732, compound

Product 1

HCID 59077637HCID 59077637, compoundYield 35.7%

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-pyrrol-3-yl}-acetic acid (200 mg, 0.38 mmol), HOBt (52 mg), EDAC (130 mg), cyclopropyl-(R)-1-piperidin-3-ylmethyl-amine (103 mg) and TEA (7 drops) in DMF (2 mL) was stirred at rt for overnight. The reaction was concentrated and purified on a silica gel column to give 89 mg of the titled compound.

Workup

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

Sources & evidence

ORD record
ord-4b9be7080a8941419b69ee5d6639fc66
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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