Diisopropylethylamine → 1-(5-tert-butyl-3-(2-cyanopropan-2-yl)-2-methoxyphenyl)-3-((1S,2R)-1-hydroxy-2,3-dihydro-1H-indene-2-yl)urea

HRID 243813

Reaktionsgleichung

[C:1]([C:5]1[CH:6]=[C:7]([C:22]([C:25]#[N:26])([CH3:24])[CH3:23])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:27][C@@H:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C@@H:29]1[OH:37].C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([C:22]([C:25]#[N:26])([CH3:23])[CH3:24])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12]([NH:27][C@@H:28]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C@@H:29]2[OH:37])=[O:19])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

To a solution of 2,2,2-trichloroethyl 5-tert-butyl-3-(2-cyanopropan-2-yl)-2-methoxyphenylcarbamate (0.086 g, 0.203 mmol) and (1S,2R)-2-amino-2,3-dihydro-1H-indene-1-ol.L-tartaric acid salt (0.067 g, 0.223 mmol) in acetonitrile (0.8 mL), N,N-diisopropylethylamine (0.058 mL, 0.333 mmol) was added, the mixture was stirred overnight at 110° C. The reaction mixture was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=10/90-60/40) to obtain 0.044 g of the captioned compound (51% yield).

Aufarbeitung

customThe reaction mixture was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=10/90-60/40)

Quellen und Nachweise

ORD-Eintrag: ord-bcc932fdcde14f20ba571ba2466d1d37
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653304B2

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