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

HRID 390697노트

반응식

HRID 390697 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3361b4dd6d064fbda346cbc512b634a0
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383657B2

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