1-Hydroxybenzotriazole → 5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [2-(3-Acetylamino-pyrrolidin-1-yl)-ethyl]-amide

HRID 1359807Notes

Reaction equation

HRID 1359807 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.Cl.[NH2:56][CH2:57][CH2:58][N:59]1[CH2:63][CH2:62][CH:61]([NH:64][C:65](=[O:67])[CH3:66])[CH2:60]1>CN(C=O)C>[C:65]([NH:64][CH:61]1[CH2:62][CH2:63][N:59]([CH2:58][CH2:57][NH:56][C:30]([C:26]2[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]3\[C:17](=[O:22])[NH:18][C:19]4[C:15]\3=[CH:14][C:13]([S:10]([CH2:9][C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])(=[O:11])=[O:12])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])=[O:32])[CH2:60]1)(=[O:67])[CH3:66]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23450282N-[1-(2-Amino-ethyl)-pyrrolidin-3-yl]-acetamideHCID 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 590777625-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [2-(3-Acetylamino-pyrrolidin-1-yl)-ethyl]-amideYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (252 mg, 0.5 mmol) in DMF (10 mL) was added HOBt (101 mg, 1.5 eq.), EDAC.HCl (144 mg, 1.5 eq.) and TEA (152 mg, 3 eq.). After stirring at rf for 30 mins, to the mixture was added N-[1-(2-amino-ethyl)-pyrrolidin-3-yl]-acetamide (128 mg, 1.5 eq.). After stirring at 30° C. for 72 hours, the reaction was concentrated and the residue was purified on a silica gel column to give 213 mg (65%) of the titled compound as an orange solid.

Workup

  1. stirringAfter stirring at 30° C. for 72 hours
  2. concentrationthe reaction was concentrated
  3. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-5fc4b8ac715443d79dd303f4cf66a4ac
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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