Dimethyl Sulfoxide → HCID 11999853, Verbindung

HRID 2246835

Reaktionsgleichung

ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[CH:23][CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[CH3:37][N:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH2:43][NH2:44].CS(C)=O.C(N(CC)CC)C>C(#N)C.CCCCCC.C(OCC)(=O)C>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:44][CH2:43][C:39]4[N:38]([CH3:37])[CH:42]=[CH:41][CH:40]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:20])=[CH:26][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a suspension of 2,2,2-trichloro-1-{10-[(2′-methoxy-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 1 (1.175 g, 2.17 mmole) in acetonitrile (15 mL) was added (1-methyl-1H-pyrrol-2-yl)methylamine (0.263 g, 2.38 mmole) followed by dimethylsulfoxide (0.710 g, 9.06 mmole) and triethylamine (0.400 g, 4 mmole). The mixture was heated under nitrogen at 80° C. for 4 hours. The solvent was removed in vacuo, and the residue was flash chromatographed on silica Merck-60 using a gradient of 0-25% of ethyl acetate in dichloromethane, to provide a yellow foam that yields a solid (0.464 g) upon treatment with ethyl acetate and hexane, mp 148-150° C.

Aufarbeitung

customThe solvent was removed in vacuo
customchromatographed on silica Merck-60
customto provide a yellow foam

Quellen und Nachweise

ORD-Eintrag: ord-8a4f9b1cfbc84c51972a44d3dc84ab72
Quelldatensatz: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07687623B2

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