Dimethylformamide → N,N-diethylethanamine;methyl butanoate

HRID 323234

Reaktionsgleichung

[CH3:1][O:2][C:3]1C=[C:5]([CH:39]=[C:40](OC)[C:41]=1OC)[C:6]([N:8]1[CH2:12][CH2:11][C:10](CCN2CCC(NC3NC4C=CC=CC=4N=3)CC2)(C2C=CC(Cl)=C(Cl)C=2)[CH2:9]1)=O.CN(C)C=[O:49].[H-].[Na+].C(OCCCl)C>ClCCl.CO.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:40]([CH2:41][C:3]([O:2][CH3:1])=[O:49])[CH3:39].[CH2:6]([N:8]([CH2:12][CH3:11])[CH2:9][CH3:10])[CH3:5]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine (0.54 g, 0.82 mmol) and dimethylformamide (15 mL). Add sodium hydride (0.07 g, 60% in oil, 1.8 mmol). After 1 hour, add 2-chloroethyl ethyl ether (1 mL). Heat to 100° C. After 18 hours, cool to ambient temperature and dilute the reaction mixture with dichloromethane. Extract three times with water, dry the organic layer over Na2SO4, filter and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 25/75/1 methanol/ethyl acetate/triethylamine. Collect the product containing fractions, evaporate in vacuo to give a residue, and chromatograph on silica gel eluting with 20/80/0.5 methanol ethyl acetate/triethylamine to give the title compound: Rf=0.23 (silica gel, 30% methanol/ethyl acetate).

Aufarbeitung

waitAfter 18 hours
temperaturecool to ambient temperature
extractionExtract three times with water
dry with materialdry the organic layer over Na2SO4
filtrationfilter
customevaporate in vacuo
customto give a residue
customCollect the product
additioncontaining fractions
customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-ba28978f1ed94c70867ed611c4592984
Quelldatensatz: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06211199B1

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