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 1520495노트

반응식

HRID 1520495 반응식
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]

참가 물질

4

반응물 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

생성물 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-ethanone수율 12%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d971a05c98a441cd94c385fa57b42fd7
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073894B2

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