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

HRID 724729

反応式

HRID 724729 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-43b866aa4e534fa891134f373c1754f0
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

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