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

HRID 1509331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509331
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[CH2:9][O:8][C:7]3[N:12]=[C:13]([C:22]4[CH:36]=[CH:35][C:25]([CH2:26][NH:27]C(=O)OC(C)(C)C)=[CH:24][CH:23]=4)[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:15][C:6]2=3)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[NH2:27][CH2:26][C:25]1[CH:35]=[CH:36][C:22]([C:13]2[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:15][C:6]3[N:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)[C:10](=[O:11])[CH2:9][O:8][C:7]=3[N:12]=2)=[CH:23][CH:24]=1

Komponenten

3

Edukt 1

HCID 86683684tert-Butyl 4-(1-(cyclopropylmethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate

Produkt 1

HCID 532626716-(4-(Aminomethyl)phenyl)-1-(cyclopropylmethyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(1-(cyclopropylmethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate (80 mg, 0.165 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 (45 mg, 70.9%) as white solid. LCMS: RT=0.84 min, M+H+=386. 1H NMR (500 MHz, CDCl3): 8.33 (2H, br), 7.41 (1H, s), 7.27-7.26 (4H, m), 7.18 (3H, m), 7.13-7.12 (2H, m), 4.82 (2H, s), 3.94 (2H, s), 3.87-3.85 (2H, d), 1.16-1.14 (1H, m), 0.60-0.57 (2H, m), 0.48-0.45 (2H, m).

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-894ad1bac52448258fd61f78bbb0ddda
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221838B2

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