Nitrogen → N1-(2-Fluoro-4-(trifluoromethoxy)benzyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)benzene-1,2-diamine

HRID 1527740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527740
[F:1][C:2]1[CH:26]=[C:25]([O:27][C:28]([F:31])([F:30])[F:29])[CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=2)[CH:9]=[CH:8][C:7]=1[N+:20]([O-])=O.N#N>[Pt].C(OCC)(=O)C>[F:1][C:2]1[CH:26]=[C:25]([O:27][C:28]([F:30])([F:29])[F:31])[CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6]1[C:7]([NH2:20])=[CH:8][CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=2)[CH:11]=1

Komponenten

5

Edukt 2

HCID 947NitrogenHCID 90410701HCID 90410701, Verbindung

Produkt 1

HCID 131732437N1-(2-Fluoro-4-(trifluoromethoxy)benzyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)benzene-1,2-diamineAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a high pressure reactor a solution of N-(2-fluoro-4-(trifluoromethoxy)benzyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)-2-nitroaniline (80.0 g, 0.18 mol), 5% Pt/C (50% H2O, Johnson Matthey B102022-5) (7.1 g, 0.91 mmol) and ethyl acetate (800 mL) was filled twice with N2 (60 psi) then twice with H2 (60 psi). The flask was then filled with H2 (60 psi) and let stir at RT 15 h. The reaction mixture was filtered (zapcap brand filter), the solid was rinsed with EtOAc (2×200 mL). The filtrate was concentrated to dryness to afford the title compound as a brown oil (74.5 g, 99.5%). This material was used without further purification. MS (ESI): mass calcd. for C19H18F4N4O2, 410.1; m/z found, 411.1 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 7.42-7.35 (m, 1H), 7.33-7.29 (d, J=2.2, 1H), 7.01-6.94 (d, J=9.2, 1H), 6.71-6.66 (d, J=8.3, 1H), 6.37-6.31 (dd, J=8.3, 2.7, 1H), 6.31-6.26 (m, 1H), 4.98-4.94 (s, 1H), 4.41-4.33 (s, 1H), 3.93-3.85 (s, 2H), 3.35-2.72 (s, 1H).

Aufarbeitung

  1. additionThe flask was then filled with H2 (60 psi)
  2. filtrationThe reaction mixture was filtered
  3. filtration(zapcap brand filter)
  4. washthe solid was rinsed with EtOAc (2×200 mL)
  5. concentrationThe filtrate was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bb6fad8bf57d4e8aabec63bbcf468442
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089569B2

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