Trifluoroacetic acid → HCID 136337770, Verbindung

HRID 871333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871333
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]([NH:26][C:27]([NH:29][C:30]4[CH:34]=[C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])[O:32][N:31]=4)=[O:28])[CH:23]=[CH:24][CH:25]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[C:35]([C:33]1[O:32][N:31]=[C:30]([NH:29][C:27]([NH:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][C:13]3[C:12]4[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=4)[N:16]=[CH:15][N:14]=3)[CH:21]=2)=[O:28])[CH:34]=1)([CH3:38])([CH3:36])[CH3:37]

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 668764501-(3-(7-(Benzyloxy)quinazolin-4-yloxy)phenyl)-3-(5-tert-butylisoxazol-3-yl)urea

Produkt 1

HCID 136337770HCID 136337770, VerbindungAusbeute 60,1 %

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

1-(3-(7-(Benzyloxy)quinazolin-4-yloxy)phenyl)-3-(5-tert-butylisoxazol-3-yl)urea (725 mg, 1.42 mmol) was treated with trifluoroacetic acid (7 mL) and heated at 85° C. for 3 h. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate/water. The solution was neutralized with saturated sodium bicarbonate (pH=8) and the organic layer separated. After extraction of the aqueous phase with ethyl acetate, the organic fractions were combined, dried (MgSO4) and concentrated under reduced pressure. The solid was triturated with ethyl acetate to afford 1-(5-tert-butylisoxazol-3-yl)-3-(3-(7-hydroxyquinazolin-4-yloxy)phenyl)urea (358 mg, 60%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.92 (s, 1H), 9.64 (s, 1H), 9.07 (s, 1H), 8.58 (s, 1H), 8.24 (d, 1H), 7.57 (s, 1H), 7.41 (t, 1H), 7.30 (d, 2H), 7.20 (s, 1H), 6.97 (d, 1H) 6.49 (s, 1H), 1.27 (s, 9H); LC-MS (ESI) m/z 420 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate/water
  3. customthe organic layer separated
  4. extractionAfter extraction of the aqueous phase with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe solid was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cef3d8fdebcd4299b0137de076eaf13d
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969587B2

Notizen zur Reaktion

Wird geladen…