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 525564ノート

反応式

HRID 525564 の反応式
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]

参加物

4

反応物 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

生成物 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-ethanone収率 12%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5732b0007d6b4611904c8ef644e4f327
出典データセット
uspto-grants-2016_05
特許番号
US09340564B2

反応ノート

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