tert-Butyl 4-(1-ethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate → 6(4-(Aminomethyl)phenyl)-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1509329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509329
[CH2:1]([N:3]1[C:8](=[O:9])[CH2:7][O:6][C:5]2[N:10]=[C:11]([C:20]3[CH:34]=[CH:33][C:23]([CH2:24][NH:25]C(=O)OC(C)(C)C)=[CH:22][CH:21]=3)[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:13][C:4]1=2)[CH3:2]>C(O)(C(F)(F)F)=O>[NH2:25][CH2:24][C:23]1[CH:33]=[CH:34][C:20]([C:11]2[C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][C:4]3[N:3]([CH2:1][CH3:2])[C:8](=[O:9])[CH2:7][O:6][C:5]=3[N:10]=2)=[CH:21][CH:22]=1

Komponenten

3

Edukt 1

HCID 86683682tert-Butyl 4-(1-ethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate

Produkt 1

HCID 532626706(4-(Aminomethyl)phenyl)-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(1-ethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate (45 mg, 0.098 mmol) was dissolved in TFA (1 mL). The resulting mixture was stirred for 30 seconds at room temperature and evaporated under reduced pressure. The deprotected compound was taken back twice into diethyl ether and the solid formed was washed twice with diethylether. The remaining solvent was removed under reduced pressure and dried to afford the title compound (35 mg, 99%) as white solid. LCMS: RT=0.75 min, M+H+=360. 1H NMR (500 MHz, CDCl3): 8.34 (2H, br), 7.30-7.27 (5H, m), 7.18 (3H, m), 7.13-7.11 (2H, m), 4.80 (2H, s), 4.03-3.99 (2H, q), 3.96 (2H, s), 1.32-1.30 93H, t).

Aufarbeitung

  1. customevaporated under reduced pressure
  2. customthe solid formed
  3. washwas washed twice with diethylether
  4. customThe remaining solvent was removed under reduced pressure
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-85b42f0efe79427983e95a90075b7861
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221838B2

Notizen zur Reaktion

Wird geladen…