Water → 4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)-N-pyridin-3-ylpiperazine-1-carboxamide

HRID 2263172ノート

反応式

HRID 2263172 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[CH3:16][C:17]1[S:21][C:20]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[N:19][C:18]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH3:16][C:17]1[S:21][C:20]([N:22]2[CH2:27][CH2:26][N:25]([C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:15])[CH2:24][CH2:23]2)=[N:19][C:18]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 172338685-Methyl-4-phenyl-2-piperazinyl-1,3-thiazoleHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamate

生成物 1

HCID 687787184-(5-methyl-4-phenyl-1,3-thiazol-2-yl)-N-pyridin-3-ylpiperazine-1-carboxamide収率 23.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (229 mg, 0.848 mmol), 1-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine (200 mg, 0.771 mmol) and diisopropylethylamine (0.148 ml, 0.848 mmol) in dimethylsulfoxide (2.6 ml) was stirred at 70° C. for 5 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 68.4 mg (23.4%) of the desired product as a solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

出典と根拠

ORDレコード
ord-3130c8a698eb4f47af0643d9ed756ed7
出典データセット
uspto-grants-2010_12
特許番号
US07851473B2

反応ノート

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