Dimethyl Sulfoxide → 4-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-[4-(propionylamino)phenyl]piperazine-1-carboxamide

HRID 2263238ノート

反応式

HRID 2263238 の反応式
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3].[C:21]1([C:27]2[N:31]=[C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[S:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:21]1([C:27]2[N:31]=[C:30]([N:32]3[CH2:37][CH2:36][N:35]([C:13]([NH:12][C:9]4[CH:8]=[CH:7][C:6]([NH:5][C:1](=[O:4])[CH2:2][CH3:3])=[CH:11][CH:10]=4)=[O:20])[CH2:34][CH2:33]3)[S:29][N:28]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 866255132,2,2-Trichloroethyl [4-(propionylamino)phenyl]carbamate

生成物 1

HCID 687800804-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-[4-(propionylamino)phenyl]piperazine-1-carboxamide収率 29.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 2,2,2-trichloroethyl [4-(propionylamino)phenyl]carbamate (200 mg, 0.589 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (145 mg, 0.589 mmol), diisopropylethylamine (0.206 ml, 1.18 mmol) and dimethyl sulfoxide (4 ml) was stirred at 70° C. for 24 hours, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to give 76.0 mg (29.6%) 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 recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-404e25055ec8473da0b48f9592f6c140
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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