1-Hydroxybenzotriazole → HCID 59077764, compound

HRID 1359717Notes

Reaction equation

HRID 1359717 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:25][C:26]([CH3:32])=[CH:27][C:28]=1[C:29](O)=[O:30])(=[O:12])=[O:11].[CH3:33][C@@H:34]1[CH2:39][NH:38][CH2:37][C@H:36]([CH3:40])[NH:35]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(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:23]\[C:24]1[NH:25][C:26]([CH3:32])=[CH:27][C:28]=1[C:29]([N:38]1[CH2:37][C@H:36]([CH3:40])[NH:35][C@H:34]([CH3:33])[CH2:39]1)=[O:30])(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 59077650HCID 59077650, compound

Product 1

HCID 59077764HCID 59077764, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (120 mg, 0.24 mmol), (2R,6S)-2,6-dimethyl-piperazine (32 mg, 1.2 eq.), HOBt (1.2 eq.), EDAC.HCl (1.2 eq.) and TEA (3 eq.) in DMF (10 mL) was stirred at rt for overnight. The reaction was concentrated and purified on s silica gel column to give the titled compound.

Workup

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

Sources & evidence

ORD record
ord-4b09ccf9673045c5a40572dd32a245f9
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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