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

HRID 2263244ノート

反応式

HRID 2263244 の反応式
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[N:32]=[C:31]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[S:30][N:29]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:23]1([C:28]2[N:32]=[C:31]([N:33]3[CH2:38][CH2:37][N:36]([C:13]([NH:12][C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[CH:4][CH:3]=[N:2]5)=[CH:11][CH:10]=4)=[O:20])[CH2:35][CH2:34]3)[S:30][N:29]=2)[CH:22]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 687757201-[3-(2-Fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazineHCID 862452022,2,2-Trichloroethyl [4-(1H-pyrazol-1-yl)phenyl]carbamate

生成物 1

HCID 687763734-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-[4-(1H-pyrazol-1-yl)phenyl]piperazine-1-carboxamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 2,2,2-trichloroethyl [4-(1H-pyrazol-1-yl)phenyl]carbamate (200 mg, 0.598 mmol), 1-[3-(2-fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine (147 mg, 0.598 mmol), diisopropylethylamine (0.208 ml, 1.20 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 purified by silica gel column chromatography (ethyl acetate) to give the desired product as a solid. The solid was recrystallized from ethyl acetate to give 63.7 mg (24.7%) 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)

出典と根拠

ORDレコード
ord-ebd64d3764084d729889c50b509fed72
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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