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Ethoxyacetyl chloride → 1-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol

HRID 598324
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598324
C(OC1C=C2C(=CC=1)N=CC([N+]([O-])=O)=C2[Cl:22])C1C=CC=CC=1.C(OC1C=C2C(C(Cl)=C([N+]([O-])=O)C=N2)=CC=1)C1C=CC=CC=1.[CH2:45]([O:47][CH2:48][C:49](Cl)=[O:50])[CH3:46].[NH2:52][C:53]1[CH:54]=[N:55][C:56]2[C:61]([C:62]=1[NH:63][CH2:64][C:65]([CH3:68])([OH:67])[CH3:66])=[CH:60][C:59]([O:69][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)=[CH:58][CH:57]=2>C(#N)C>[NH2:52][C:53]1[CH:54]=[N:55][C:56]2[C:61]([C:62]=1[NH:63][CH2:64][C:65]([CH3:66])([OH:67])[CH3:68])=[CH:60][C:59]([O:69][CH2:70][C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[CH:58][CH:57]=2.[ClH:22].[CH2:70]([O:69][C:59]1[CH:60]=[C:61]2[C:56](=[CH:57][CH:58]=1)[N:55]=[CH:54][C:53]([NH:52][C:49](=[O:50])[CH2:48][O:47][CH2:45][CH3:46])=[C:62]2[NH:63][CH2:64][C:65]([OH:67])([CH3:66])[CH3:68])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1
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Komponenten

7

Edukt 4

HCID 84189Ethoxyacetyl chlorideHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinolineHCID 670509451-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-olHCID 670509926-(Benzyloxy)-4-chloro-3-nitroquinoline

Produkt 2

HCID 670509451-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol
HCID 67051090
N-{6-benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-ethoxyacetamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol was prepared according to the general methods described in Parts A and B of Example 54 using 6-benzyloxy-4-chloro-3-nitroquinoline in lieu of 7-benzyloxy-4-chloro-3-nitroquinoline in Part A. Ethoxyacetyl chloride (5.37 g, 43.8 mmol) was added to a solution of 1-{[3-amino-6-(benzyloxy)quinoline-4-yl]amino}-2-methylpropan-2-ol (7.45 g, 22.1 mmol) in acetonitrile (230 mL), and the reaction was stirred overnight. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane. The resulting solution was washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on a HORIZON HPFC system (an automated, modular high-performance flash purification product available from Biotage, Inc, Charlottesville, Va., USA) (silica gel cartridge, eluting with dichloromethane:methanol ranging in ratios from 98:2 to 95:5) to provide N-{6-benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-ethoxyacetamide hydrochloride.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resulting solution was washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on a HORIZON HPFC system (
  8. custommodular high-performance flash purification product available from Biotage, Inc, Charlottesville, Va
  9. wash, USA) (silica gel cartridge, eluting with dichloromethane:methanol ranging in ratios from 98:2 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-24b3996053e545b7bb1679cd9e134c88
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897597B2

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