1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-oxo-2-((s)-3-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359813
[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.[N:56]1([CH2:61][C@@H:62]2[CH2:67][CH2:66][CH2:65][NH:64][CH2:63]2)[CH2:60][CH2:59][CH2:58][CH2:57]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](=[O:32])[N:64]2[CH2:65][CH2:66][CH2:67][C@@H:62]([CH2:61][N:56]3[CH2:57][CH2:58][CH2:59][CH2:60]3)[CH2:63]2)[C:25]=1[CH3:34])(=[O:12])=[O:11]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7183063(r)-3-Pyrrolidin-1-ylmethyl-piperidineHCID 59077497HCID 59077497, Verbindung

Produkt 1

HCID 590775165-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-oxo-2-((s)-3-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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 (156 mg, 0.3 mmol), HOBt (80 mg) and EDAC (110 mg) in DMF (4 mL) was added TEA (3 drops). After stirring at rt for 2 hours, to the mixture was added (R)-3-pyrrolidin-1-ylmethyl-piperidine (250 mg). After stirring at rt for overnight, the reaction was concentrated and dissolved in ethyl acetate. It was then washed with water and sodium bicarbonate, dried and concentrated. The residue was purified on a silica gel column to give 172 mg of the titled compound. MS m/z 667 [M−1].

Aufarbeitung

  1. stirringAfter stirring at rt for overnight
  2. concentrationthe reaction was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washIt was then washed with water and sodium bicarbonate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-c8e3791ac7904ebf8f75effd224959a1
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599902B2

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