Diisopropylethylamine → 3-[1-{4-[3-((s)-2-Cyclopropylaminomethyl-pyrrolidin-1-yl)-3-oxo-propyl]-3,5-dimethyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-5-(2,6-dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one

HRID 1359884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359884
[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][CH2:31][C:32]([OH:34])=O)[C:25]=1[CH3:35])(=[O:12])=[O:11].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:69]1([NH:72][CH2:73][C@@H:74]2[CH2:78][CH2:77][CH2:76][NH:75]2)[CH2:71][CH2:70]1>CN(C=O)C>[CH:69]1([NH:72][CH2:73][C@@H:74]2[CH2:78][CH2:77][CH2:76][N:75]2[C:32](=[O:34])[CH2:31][CH2:30][C:26]2[C:25]([CH3:35])=[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:12])=[O:11])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])[CH2:71][CH2:70]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 590776223-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic AcidHCID 69869739cyclopropyl-(S)-1-pyrrolidin-2-ylmethyl-amine

Produkt 1

HCID 590775863-[1-{4-[3-((s)-2-Cyclopropylaminomethyl-pyrrolidin-1-yl)-3-oxo-propyl]-3,5-dimethyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-5-(2,6-dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic acid (100 mg, 0.19 mmol) and DIPEA (45 mg, 1.9 eq.) in DMF (2 mL) was stirred at rt for 30 mins. To the mixture was added HATU (85 mg, 1.2 eq.). After stirring for another 3 hours, to the mixture was added cyclopropyl-(S)-1-pyrrolidin-2-ylmethyl-amine (29 mg, 1.1 eq.). After stirring for 72 hours, the reaction was concentrated and purified on a silica gel column to give the titled compound as an orange solid.

Aufarbeitung

  1. stirringAfter stirring for another 3 hours, to the mixture
  2. stirringAfter stirring for 72 hours
  3. concentrationthe reaction was concentrated
  4. custompurified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-878acb3a2c044237b7915ffdd70ff4fc
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599902B2

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