1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077629, compound

HRID 1359847Notes

Reaction equation

HRID 1359847 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](O)=[O:31])[C:25]=1[CH3:33])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH:55]1([NH:58][CH2:59][C@@H:60]2[CH2:65][CH2:64][CH2:63][NH:62][CH2:61]2)[CH2:57][CH2:56]1>CN(C=O)C>[CH:55]1([NH:58][CH2:59][C@@H:60]2[CH2:65][CH2:64][CH2:63][N:62]([C:30]([C:26]3[C:25]([CH3:33])=[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:12])=[O:11])=[CH:21][CH:20]=5)[NH:28][C:27]=3[CH3:29])=[O:31])[CH2:61]2)[CH2:57][CH2:56]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 590775075-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acidHCID 69869732HCID 69869732, compound

Product 1

HCID 59077629HCID 59077629, compoundYield 17.5%

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 (200 mg, 0.4 mmol), HOBt (54 mg, 1 eq.), EDAC (77 mg, 1 eq.), TEA (0.17 mL) and cyclopropyl-(R)-1-piperidin-3-ylmethyl-amine (110 mg, 0.48 mmol) in DMF (3 mL) was stirred at rt for overnight. The reaction was concentrated and purified on a silica gel column to give 45 mg of the titled compound.

Workup

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

Sources & evidence

ORD record
ord-2fbcadb5eb8a4c7285ba1d83ac0ca36a
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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