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

HRID 1359715Notes

Reaction equation

HRID 1359715 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.[CH3:56][NH:57][CH:58]1[CH2:63][CH2:62][N:61]([CH3:64])[CH2:60][CH2:59]1>CN(C=O)C>[CH3:56][N:57]([CH:58]1[CH2:63][CH2:62][N:61]([CH3:64])[CH2:60][CH2:59]1)[C:30]([C:26]1[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]2\[C:17](=[O:22])[NH:18][C:19]3[C:15]\2=[CH:14][C:13]([S:10]([CH2:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])(=[O:11])=[O:12])=[CH:21][CH:20]=3)[NH:28][C:27]=1[CH3:29])=[O:32]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5663231-Methyl-4-(methylamino)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 590776115-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid Methyl-(1-methyl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 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 (100 mg, 0.2 mmol), HOBt (33 mg, 1.2 eq.), EDAC.HCl (45 mg, 1.2 eq.) and methyl-(1-methyl-piperidin-4-yl)-amine (284 mg, 1.1 eq.) in DMF (2 mL) was added TEA (0.069 mL, 2.5 eq.). After stirring at rt for 2 days, the reaction was concentrated, diluted with DCM and added solid sodium bicarbonate. After stirring at rt for 15 mins, the suspension was loaded onto a silica gel column to give the titled compound as an orange solid.

Workup

  1. concentrationthe reaction was concentrated
  2. additiondiluted with DCM
  3. additionadded solid sodium bicarbonate
  4. stirringAfter stirring at rt for 15 mins

Sources & evidence

ORD record
ord-576f522900e644358124f6e503929ffe
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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