Ethanol → 3-((3-(1,1,2,2-Tetrafluoroethoxy)benzyl)(3-(4-aminophenoxy)phenyl)amino)-1,1,1-trifluoropropan-2-ol

HRID 990407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990407
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([O:8][C:9]2[CH:10]=[C:11]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:36])([F:35])[CH:32]([F:34])[F:33])[CH:25]=3)[CH2:16][CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H].[CH2:41](O)[CH3:42]>[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[C:11]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:35])([F:36])[CH:32]([F:33])[F:34])[CH:25]=3)[CH2:16][CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:13][CH:14]=2)=[CH:37][CH:38]=1.[CH2:41]([NH:1][C:4]1[CH:38]=[CH:37][C:7]([O:8][C:9]2[CH:10]=[C:11]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:36])([F:35])[CH:32]([F:34])[F:33])[CH:25]=3)[CH2:16][CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)[CH3:42]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 111244671,1,1-Trifluoro-3-((3-(4-nitrophenoxy)phenyl)(3-(1,1,2,2-tetrafluoroethoxy)benzyl)amino)propan-2-olHCID 178418361HCID 178418361, Verbindung

Produkt 2

HCID 110818833-((3-(1,1,2,2-Tetrafluoroethoxy)benzyl)(3-(4-aminophenoxy)phenyl)amino)-1,1,1-trifluoropropan-2-olHCID 235060983-[[3-(4-(Ethylamino)phenoxy]phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A solution of 3-[[3-(4-nitrophenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy) phenyl]-methyl]amino]-1,1,1-trifluoro-2-propanol (33.8 mg, 0.06 mmol) in ethanol and 5% palladium on carbon (4 mL) was placed under 40 psi hydrogen gas for 7H. The mixture was filtered through celite, the solvent was evaporated, and the residue was purified by silica gel chromatography eluting with 25% ethyl acetate in hexane to give 13.4 mg (42%) of (EX-450A) as 3-[[3(4-aminophenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy) phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol and 13.9 mg (41%) of (EX-450B) as 3-[[3-[4-(ethylamino)phenoxy]phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol both as orange oils. 3-[[3-(4-aminophenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-amino]-1,1,1-trifluoro-2-propanol: HRMS calcd. for C24H22F7N2)3: 519.1519 [M+H]+, found: 519.1529. 1H NMR (acetone-d6) δ3.63 (dd, 1H), 3.96 (dd, 1H), 4.42-4.58 (m, 1H), 4.80 (s, 2H), 5.88 (m, 1H), 6.20 (m, 1H), 6.32-6.77 (m, 6H), 6.92 (d, 1H), 7.06-7.26 (m, 3H), 7.43 (m, 1H). 3-[[3-[4-(ethylamino)phenoxyphenyl][[3-(1,1,2,2-tetrafluoroethoxy) phenyl]-methyl]amino]-1,1,1-trifluoro-2-propanol: HRMS calcd. for C26H26F7N2O3: 547.1832 [M+H]+. found: 547.1819. 1H NMR (acetone-d6) δ1.23 (t, 3H), 3.17 (q, 2H), 3.63 (dd, 1H), 3.96 (dd, 1H), 4.424.58 (m, 1H), 4.79 (s, 2H), 5.85 (d, 1H), 6.20 (m, 1H), 6.33 (m, 1H), 6.47 (m, 1H), 6.50 (tt, 1J), 6.61 (d, 2H), 6.78 (d, 2H), 7.09 (t, 1H), 7.20 (m, 1H), 7.23 (d, 1H), 7.42 (m, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 25% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-3bdc39b8c35748f986ed396b4224efea
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458803B1

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