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 1359715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359715
[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]

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-576f522900e644358124f6e503929ffe
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599902B2

Notizen zur Reaktion

Wird geladen…