HCID 178473565, Verbindung → HCID 123386190, Verbindung

HRID 1509137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509137
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:21][C:22]4[NH:27][C:26](=[N:28][NH:29][C:30](OCC)=[O:31])[CH2:25][O:24][C:23]=4[N:35]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:21][C:22]4[N:27]5[C:30](=[O:31])[NH:29][N:28]=[C:26]5[CH2:25][O:24][C:23]=4[N:35]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 178473565HCID 178473565, Verbindung

Produkt 1

HCID 123386190HCID 123386190, VerbindungAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of Ethyl 2-(6-(4-(1-(tert-butoxycarbonylamino)cyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ylidene)hydrazinecarboxylate (24 mg, 0.04 mmol) in dry DMF (1 mL) was heated at 200° C. for 10 min under microwave irradiation. The reaction mixture was diluted with dichloromethane, filtered on celite and concentrated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O) to give the title compound (7 mg, 32%). 1H NMR (500 MHz, CDCl3): 9.18 (1H, br s), 8.54 (1H, s), 7.32 (2H, d), 7.28-7.26 (5H,m), 7.22-7.20 (2H,m), 5.32 (2H, s), 5.07 (1H, br s), 2.55-2.25 (4H, m), 2.10-2.03 (1H, m), 1.86-1.78 (1H, m), 1.44-1.15 (9H, br).

Aufarbeitung

  1. filtrationfiltered on celite and
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe resulting residue was purified by preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-5c67a51b6c4048dab4de873ad17ebe22
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221838B2

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