1-Hydroxybenzotriazole → 2-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-[2-(3-oxo-piperazin-1-yl)-ethyl]-acetamide

HRID 1359720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359720
[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]([CH2:30][C:31](O)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:57][CH2:58][CH2:59][N:60]1[CH2:65][CH2:64][NH:63][C:62](=[O:66])[CH2:61]1>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:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([NH:57][CH2:58][CH2:59][N:60]2[CH2:65][CH2:64][NH:63][C:62](=[O:66])[CH2:61]2)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11]

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71759914-(2-Aminoethyl)piperazin-2-oneHCID 59077497HCID 59077497, Verbindung

Produkt 1

HCID 590776422-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-[2-(3-oxo-piperazin-1-yl)-ethyl]-acetamide

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-pyrrol-3-yl}-acetic acid (100 mg, 0.19 mmol), HOBt (3 mg, 0.1 eq.), EDAC.HCl (44 mg, 1.2 eq.) and 4-(2-amino-ethyl)-piperazin-2-one (30 mg, 1.1 eq.) in DMF (2 mL) at rt was added TEA (0.067 mL, 2.5 eq.). After stirring at rt for 7 days, the reaction was concentrated, diluted with DCM and then mixed with 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 a pale orange solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6765fb974eb340f6902159e19f75f8aa
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599902B2

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