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Water → 4-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]-N-pyridin-3-ylpiperazine-1-carboxamide

HRID 2263281
ノート
印刷プレビュー

反応式

HRID 2263281 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.Cl[C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH:20]=[CH:21][CH:22]=1.[CH:34]([N:37](C(C)C)CC)(C)C.O>CS(C)=O>[C:34]([C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH:20]=[CH:21][CH:22]=1)#[N:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 617805201-[4-(3-Chlorophenyl)-1,3-thiazol-2-yl]piperazineHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamate

生成物 1

HCID 687781214-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]-N-pyridin-3-ylpiperazine-1-carboxamide収率 26.5%

試薬・触媒・溶媒 1

HCID 679
Dimethyl 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 (219 mg, 0.814 mmol), 1-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.740 mmol) and diisopropylethylamine (0.258 ml, 1.48 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 15 hours. Water was poured to the reaction mixture, 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 76.6 mg (26.5%) 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-bb2ee7bd9ce14819903ed24481e22b63
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07851473B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート