HCID 67262173, Verbindung → HCID 67256554, Verbindung

HRID 1509199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509199
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:24]=[C:23]([N:25]([CH3:31])[CH2:26][C:27]([O:29]C)=O)[C:22]([N+:32]([O-])=O)=[CH:21][C:20]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:20]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:21][C:22]4[NH:32][C:27](=[O:29])[CH2:26][N:25]([CH3:31])[C:23]=4[N:24]=3)=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 2

HCID 67262173HCID 67262173, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67256554HCID 67256554, VerbindungAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a glass autoclave were added methyl 2-((6-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-3-nitro-5-phenylpyridin-2-yl)(methyl)amino)acetate (800 mg, 1.46 mmol) and 10% palladium on carbon (300 mg, 0.28 mmol) in THF (100 ml). The solution was hydrogenated at room temperature under 1.5 atm hydrogen for 20 hours. The reaction mixture was filtered through celite, then concentrated to dryness under reduced pressure. The residue was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 100:0 to 0:100) to afford the title compound (270 mg, 38%). 1H NMR (500 MHz, CDCl3): 7.35 (2H, d), 7.20-7.33 (5H, m), 7.15 (2H, d), 6.98 (1H, s), 5.05 (1H, br s), 4.11 (2H, s), 3.18 (3H, s), 2.20-2.70 (4H, br m), 2.00-2.14 (1H, m), 1.77-1.87 (1H, m), 1.10-1.50 (9H, br).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 100:0 to 0:100)

Quellen und Nachweise

ORD-Eintrag
ord-9dd886e034d54a6bb91270d06c182ec3
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221838B2

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