Acetonitrile → 4-(4-Fluorophenyl)-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1,2,3,6-tetrahydropyridine

HRID 724729

반응식

HRID 724729 반응식
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)=[CH:5][CH:4]=1.FC(F)(F)S([O-])(=O)=O.[CH3:23][C:24]1[N:25]([S:30](N2C=CN=C2C)(=[O:32])=[O:31])[CH:26]=[CH:27][N+:28]=1C.C(#N)C.C(N(CC)CC)C>O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][N:12]([S:30]([N:25]3[CH:26]=[CH:27][N:28]=[C:24]3[CH3:23])(=[O:32])=[O:31])[CH2:11][CH:10]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochlorideHCID 108728322,3-dimethyl-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1H-imidazol-3-ium trifluoromethanesulfonate

생성물 1

HCID 218786854-(4-Fluorophenyl)-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1,2,3,6-tetrahydropyridine수율 52%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (150 mg, 700 μmol), 2,3-dimethyl-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1H-imidazol-3-ium trifluoromethanesulfonate (410 mg, 1.05 mmol), acetonitrile (5 mL) and triethylamine (98 μL, 700 μmol) was stirred at 25° C. for 24 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by preparative LCMS to yield the desired product (117 mg, 52%). MF=C15H16FN3O2S; LCMS found for C15H17FN3O2S(M+H)+: m/z=322.

후처리

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative LCMS

출처 및 근거

ORD 기록
ord-43b866aa4e534fa891134f373c1754f0
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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