Pyridine → HCID 71259078, Verbindung

HRID 1482918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1482918
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:24][CH3:25])=[C:5]([CH3:26])[O:4][N:3]=1.N1C=CC=CC=1.[O:33]1[CH2:38][CH2:37][CH:36]([C:39](Cl)=[O:40])[CH2:35][CH2:34]1>C(Cl)Cl>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])=[C:12]([NH:17][C:39]([CH:36]4[CH2:37][CH2:38][O:33][CH2:34][CH2:35]4)=[O:40])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:24][CH3:25])=[C:5]([CH3:26])[O:4][N:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 2795505Oxane-4-carbonyl chlorideHCID 709803797-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(1-methoxypropan-2-yl)quinoline-3,4-diamine

Produkt 1

HCID 71259078HCID 71259078, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(1-methoxypropan-2-yl)quinoline-3,4-diamine (for a preparation see Intermediate 2) (9.1 g) in DCM (300 ml) was treated with pyridine (30 ml) and tetrahydro-2H-pyran-4-carbonyl chloride (5.0 ml) and the solution stirred under nitrogen at ambient temperature for 3.5 h and then left standing overnight (ambient temperature, under nitrogen). The volatiles were evaporated in vacuo and the residue partitioned between DCM and water. The organic phase was washed with water ×2 and the combined aqueous extracted with DCM. The combined organic phases were washed with brine, dried (hydrophobic frit) and reduced to dryness in vacuo. The combined aqueous including the brine wash (˜pH4) was basified with solid sodium hydrogen carbonate and the aqueous extracted with DCM ×2. The organic fractions were dried (hydrophobic frit), combined with the previous material and reduced to dryness in vacuo to give a brown foam. This foam was further dried in vacuo, triturated with diethyl ether, the suspension chilled (ice/water bath) and the solid isolated by filtration. The solid was washed with a little diethyl ether and air-dried to give N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-4-((1-methoxypropan-2-yl)amino)quinolin-3-yl)tetrahydro-2H-pyran-4-carboxamide as a beige solid (11.95 g, 100%).

Aufarbeitung

  1. waitleft
  2. waitstanding overnight
  3. custom(ambient temperature, under nitrogen)
  4. customThe volatiles were evaporated in vacuo
  5. customthe residue partitioned between DCM and water
  6. washThe organic phase was washed with water ×2
  7. extractionthe combined aqueous extracted with DCM
  8. washThe combined organic phases were washed with brine
  9. customdried (hydrophobic frit)
  10. washwash (˜pH4)
  11. extractionthe aqueous extracted with DCM ×2
  12. customThe organic fractions were dried (hydrophobic frit)
  13. customto give a brown foam
  14. customThis foam was further dried in vacuo
  15. customtriturated with diethyl ether
  16. temperaturethe suspension chilled (ice/water bath)
  17. customthe solid isolated by filtration
  18. washThe solid was washed with a little diethyl ether
  19. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-92eeb71a5c234c388d3f9024c0dc7261
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416130B2

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