Triethylamine → tert-butyl(1-(4-(1-(dimethylamino)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate

HRID 1509279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509279
Br[C:2]1[N:6]2[C:7]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:12]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)=[N:11][C:8]=3[O:9][CH2:10][C:5]2=[N:4][N:3]=1.Cl.[CH3:40][NH:41][CH3:42].C(N(CC)CC)C>CN1C(=O)CCC1.C(Cl)Cl.O>[C:34]([O:33][C:32](=[O:38])[NH:31][C:27]1([C:24]2[CH:23]=[CH:22][C:21]([C:12]3[C:13]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:14][C:7]4[N:6]5[C:2]([N:41]([CH3:42])[CH3:40])=[N:3][N:4]=[C:5]5[CH2:10][O:9][C:8]=4[N:11]=3)=[CH:26][CH:25]=2)[CH2:28][CH2:29][CH2:30]1)([CH3:36])([CH3:37])[CH3:35]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 89541876HCID 89541876, Verbindung

Produkt 1

HCID 131734407tert-butyl(1-(4-(1-(dimethylamino)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamateAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 1-(4-(1-bromo-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutylcarbamate (41 mg, 0.071 mmol), dimethylamine hydrochloride (58.2 mg, 0.714 mmol), and triethylamine (0.099 ml, 0.714 mmol) in NMP (1 ml) was heating at 130 degree for 50 min under microwave condition. The mixture was diluted with DCM (8 ml) and water (8 ml). The organic phase was washed with water (8 mlX3) and brine (5 ml). Concentrated and purified by column eluted with MeOH/DCM (0-4%) to give product (8 mg). 1H NMR (500 MHz, CDCl3) 8.15 (s, 1H), 7.15-7.34 (m, 9H), 5.51 (s, 2H), 5.01 (s, 1H), 2.95 (s, 6H), 2.4-2.5 (m, 4H), 2.0-2.15 (m, 1H), 1.75-1.85 (m, 1H), 1.2-1.35 (m, 9H).

Aufarbeitung

  1. temperaturewas heating at 130 degree for 50 min under microwave condition
  2. washThe organic phase was washed with water (8 mlX3) and brine (5 ml)
  3. concentrationConcentrated
  4. custompurified by column
  5. washeluted with MeOH/DCM (0-4%)

Quellen und Nachweise

ORD-Eintrag
ord-c2a6de8a0a574d279b37f0388547a89b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221838B2

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