1-((4R,5R)-5-{4-[6-(1-Benzylamino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl)-2,2-difluoro-ethanone → 1-((4R,5R)-5-{4-[6-(1-Amino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl)-2,2-difluoro-ethanone

HRID 525564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525564
C([NH:8][CH:9]([C:14]1[N:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C@H:26]3[O:30][C:29]([CH3:32])([CH3:31])[N:28]([C:33](=[O:37])[CH:34]([F:36])[F:35])[C@H:27]3[CH2:38][F:39])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[C:10]([F:13])([F:12])[F:11])C1C=CC=CC=1>CO.[Pd]>[NH2:8][CH:9]([C:14]1[N:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C@H:26]3[O:30][C:29]([CH3:31])([CH3:32])[N:28]([C:33](=[O:37])[CH:34]([F:36])[F:35])[C@H:27]3[CH2:38][F:39])=[CH:24][CH:25]=2)=[CH:16][CH:15]=1)[C:10]([F:13])([F:12])[F:11]

Komponenten

4

Edukt 1

HCID 866954451-((4R,5R)-5-{4-[6-(1-Benzylamino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl)-2,2-difluoro-ethanone

Produkt 1

HCID 866954471-((4R,5R)-5-{4-[6-(1-Amino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl)-2,2-difluoro-ethanoneAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred solution of 1-((4R,5R)-5-{4-[6-(1-Benzylamino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl)-2,2-difluoro-ethanone (0.22 g, 0.63 mmol) in methanol (10 mL) at room temperature is degassed with nitrogen for 10 minutes followed by addition of palladium on carbon (0.022 g, 0.0063 mmol). The reaction mixture is stirred at room temperature under hydrogen atmosphere for 16 hours. Reaction mixture is filter through celite, concentrated in vacuo. The crude material is purified by Combi flash eluting in 80% Ethyl acetate in Hexane afford the title compound (0.035 g). 1H-NMR (400 MHz, DMSO-d6) δ: 1.52 (s, 3H), 1.60 (s, 3H), 2.60-2.80 (m, 2H), 4.54-4.58 (m, 0.5H), 4.64-4.73 (m, 2H), 4.81-4.85 (m, 0.5H), 4.91-4.95 (m, 1H), 5.27 (d, J=3.6 Hz, 1H), 6.65 (t, J=52.44 HZ, 1H), 7.60 (d, J=8.28 Hz, 2H), 8.03 (m, 2H), 8.14 (d, J=8.32 Hz, 2H), 8.75 (s, 1H). LC-MS (m/z): [M+H]=462.0.

Aufarbeitung

  1. customReaction mixture
  2. filtrationis filter through celite
  3. concentrationconcentrated in vacuo
  4. customThe crude material is purified by Combi flash
  5. washeluting in 80% Ethyl acetate in Hexane

Quellen und Nachweise

ORD-Eintrag
ord-5732b0007d6b4611904c8ef644e4f327
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340564B2

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