Dimethyl Sulfide → N-(1-(3-(Methylthio)benzyl)piperidin-3-yl)-1H-indazol-5-amine

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Reaktionsgleichung

CC(C)(C)C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:21](=O)[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([S:28][CH3:29])[CH:23]=4)[CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=O.CSC>C1COCC1>[CH3:29][S:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[NH:5][N:6]=[CH:7]3)[CH2:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Into a round bottom flask was added 2,2-dimethyl-1-(5-(1-(3-(methylthio)benzoyl)-piperidin-3-ylamino)-1H-indazol-1-yl)propan-1-one (240 mg, 0.655 mmol) and THF (3 mL). The solution was heated to 60° C. and borane-dimethyl sulfide complex in THF (3.0 mL of a 2.0M solution in THF, 6.0 mmol) was added, allowing dimethyl sulfide to distill off. After the starting material was consumed, the reaction was evaporated, 5N NaOH (10 mL) was added, and the mixture was extracted with EtOAc. The organic phases were dried, evaporated, and the residue was chromatographed on silica gel, eluting with 3/1—EtOAc/Heptane to afford the title compound (95 mg, 41%).

Aufarbeitung

distillationto distill off
customAfter the starting material was consumed
customthe reaction was evaporated
addition5N NaOH (10 mL) was added
extractionthe mixture was extracted with EtOAc
customThe organic phases were dried
customevaporated
customthe residue was chromatographed on silica gel
washeluting with 3/1—EtOAc/Heptane

Quellen und Nachweise

ORD-Eintrag: ord-9b01b5d6c7a1485dac2586c9878aef59
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08071779B2

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