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

HRID 1042999

Reaktionsgleichung

Reaktionsgleichung von HRID 1042999
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-])=O.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@H:30]([NH2:32])[CH3:31]>C(#N)C>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:32][C@@H:30]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[CH3:31])=[C:3]([NH2:21])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1

Komponenten

4

Edukt 2

HCID 1084918(R)-1-Pyridin-2-yl-ethylamineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole2×

Produkt 1

HCID 672077397-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-N4-[(1R)-1-(2-pyridinyl)ethyl]-3,4-quinolinediamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-3-nitroquinoline (for a preparation see Intermediate 18, 400 mg,) and (R)-1-(pyridin-2-yl)ethanamine (293 mg) in acetonitrile (30 ml) was heated at 60° C. for 2 h. The reaction mixture was extracted with DCM and washed with a saturated solution of sodium hydrogen carbonate. The organic was dried over Na2SO4, filtered and concentrated to dryness. The resulting compound was taken-up in ether, filtered and dried in vacuo. The residue was dissolved in ethanol (20 ml) and HCl (3.8 ml). Tin (II) chloride dihydrate (0.89 g) was then added in four portions and the reaction mixture was stirred for 1 h at 40° C. The reaction mixture was hydrolysed using a solution of sodium hydroxide (1N). The mixture was extracted with DCM, the organic dried over Na2SO4, filtered over Celite and concentrated to dryness. The crude product was purified via flash column chromatography on silica gel eluting with DCM/MeOH (95/5) and the obtained product was taken-up in diisopropylether to give 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-N4-[(1R)-1-(2-pyridinyl)ethyl]-3,4-quinolinediamine (250 mg) as a brown powder. LC/MS: Rt 2.62 min.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with DCM
  2. washwashed with a saturated solution of sodium hydrogen carbonate
  3. dry with materialThe organic was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. filtrationfiltered
  7. customdried in vacuo
  8. dissolutionThe residue was dissolved in ethanol (20 ml)
  9. additionTin (II) chloride dihydrate (0.89 g) was then added in four portions
  10. extractionThe mixture was extracted with DCM
  11. dry with materialthe organic dried over Na2SO4
  12. filtrationfiltered over Celite
  13. concentrationconcentrated to dryness
  14. customThe crude product was purified via flash column chromatography on silica gel eluting with DCM/MeOH (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-3fc215738cb646b5890698dccd71952e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557984B2

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