Water → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-N4-[(1R)-1-(2-pyridinyl)ethyl]-3,4-quinolinediamine

HRID 81993

Reaktionsgleichung

[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][C@@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH3:22])=[C:12]([N+:17]([O-])=O)[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:29][CH3:30])=[C:5]([CH3:31])[O:4][N:3]=1.[Sn](Cl)Cl.[OH-].[Na+].O>CCO>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][C@@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH3:22])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:29][CH3:30])=[C:5]([CH3:31])[O:4][N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

To a suspension of 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N—((R)-1-(pyridin-2-yl)ethyl)quinolin-4-amine (Intermediate 24) (1.05 g, 2.503 mmol) in EtOH (20 mL) was added tin(II) chloride (1.66 g, 8.76 mmol) and the mixture stirred at 40° C. for 2.5 h. The reaction mixture was basified to pH 12 using 2M aq. sodium hydroxide solution. Water (30 mL) was added and the aqueous suspension extracted with DCM (3×30 mL). The organic layers were combined, dried by passing through a hydrophobic frit and concentrated to dryness under a stream of nitrogen. The resulting residue was purified by chromatography (100 g column, 2M methanolic ammonia gradient) to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4—((R)-1-(pyridin-2-yl)ethyl)quinoline-3,4-diamine (543 mg, 1.39 mmol, 56% yield) as a dark brown gum.

Aufarbeitung

extractionthe aqueous suspension extracted with DCM (3×30 mL)
customdried
concentrationconcentrated to dryness under a stream of nitrogen
customThe resulting residue was purified by chromatography (100 g column, 2M methanolic ammonia gradient)

Quellen und Nachweise

ORD-Eintrag: ord-3c6cf0887ec642e7bd1af51ddc2d7ab8
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846709B2

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