Pyrrolidine → (NZ)-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]pyrrolidine-1-carboxamide

HRID 390697ノート

反応式

HRID 390697 の反応式
[I-].C[N+]1[CH:7]=[CH:6][N:5]([C:8](/[N:10]=[C:11]2\[S:12][C:13]([CH3:26])=[CH:14][N:15]\2[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[O:9])[CH:4]=1.N1CCC[CH2:28]1.CCN(C(C)C)C(C)C>C(#N)C.ClCCl>[CH3:26][C:13]1[S:12]/[C:11](=[N:10]\[C:8]([N:5]2[CH2:6][CH2:7][CH2:28][CH2:4]2)=[O:9])/[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[CH:14]=1

参加物

6

反応物 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 87447393(NZ)-3-methyl-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]imidazol-3-ium-1-carboxamide;iodide

生成物 1

HCID 42628819(NZ)-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]pyrrolidine-1-carboxamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-methyl-1-({[(2Z)-5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2(3H)-ylidene]amino}carbonyl)-1H-imidazol-3-ium iodide (0.1 g, 0.2 mmol, Example 18B) and pyrrolidine (1.2 equivalents) in anhydrous acetonitrile (3 mL) was added Hunig's base (33 mg, 1.2 equivalents), and the resultant solution was heated at 60° C. for 3 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (25 mL) and washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude residue was chromatographed over silica using dichloromethane to give the title compound.

後処理

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was chromatographed over silica

出典と根拠

ORDレコード
ord-3361b4dd6d064fbda346cbc512b634a0
出典データセット
uspto-grants-2013_02
特許番号
US08383657B2

反応ノート

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