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 525564Notes

Reaction equation

HRID 525564 reaction equation
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]

Participants

4

Reactant 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

Product 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-ethanoneYield 12%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5732b0007d6b4611904c8ef644e4f327
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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