2,4-Pyridinedicarbonitrile → (5S)-2-(4-cyano-2-pyridyl)-4-(4-fluorophenyl)-4-(6-fluoro-3-pyridyl)-5-methyl-2-imidazoline

HRID 1455313노트

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HRID 1455313 반응식
[C:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][N:4]=1)#[N:2].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:48]2[CH:49]=[N:50][C:51]([F:54])=[CH:52][CH:53]=2)(N)[C@@H:44]([NH2:46])[CH3:45])=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]2[NH:46][C@@H:44]([CH3:45])[C:43]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)([C:48]3[CH:49]=[N:50][C:51]([F:54])=[CH:52][CH:53]=3)[N:2]=2)[CH:8]=1)#[N:10]

참가 물질

6

반응물 3

HCID 1201442,4-PyridinedicarbonitrileHCID 2733225Ytterbium triflateHCID 58649654(2S)-1-(4-fluorophenyl)-1-(6-fluoro-3-pyridyl)-1,2-propanediamine

생성물 1

HCID 178461606(5S)-2-(4-cyano-2-pyridyl)-4-(4-fluorophenyl)-4-(6-fluoro-3-pyridyl)-5-methyl-2-imidazoline수율 78.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

2,4-Dicyanopyridine (46.5 mg) and ytterbium trifluoromethanesulfonate (24 mg) were added to a solution of the optical active (2S)-1-(4-fluorophenyl)-1-(6-fluoro-3-pyridyl)-1,2-propanediamine (100 mg) described in Reference Example 5-1 in toluene (0.25 mL), and the mixture was stirred at 100° C. for 5 hours. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution in this order, and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and the organic solvent was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=2:3) to give the objective compound (106 mg) as a white solid.

후처리

  1. washwashed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution in this order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customSodium sulfate was removed by filtration
  4. customthe organic solvent was evaporated in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=2:3)

출처 및 근거

ORD 기록
ord-f3f7177c30c1402aa87329096b13a18c
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482358B2

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