Thionyl Chloride → 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide

HRID 640829

反応式

HRID 640829 の反応式
[CH2:1]([N:3]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([CH3:11])=[N:4]1)[CH3:2].S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:34]=[CH:33][C:20]([C:21]([C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27](=[O:32])[CH2:26]3)=[O:22])=[CH:19][CH:18]=1>C1COCC1>[O:32]=[C:27]1[CH2:26][C:25]2[C:29](=[CH:30][CH:31]=[C:23]([C:21]([C:20]3[CH:33]=[CH:34][C:17]([NH:16][C:8]([C:7]4[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([CH3:11])[CH:6]=4)=[O:10])=[CH:18][CH:19]=3)=[O:22])[CH:24]=2)[NH:28]1

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 27437941-Ethyl-3-methyl-1H-pyrazole-5-carboxylic acidHCID 644236235-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

生成物 1

HCID 866103732-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide収率 72.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
79 °C

実験手順

A dry 25 mL flask was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (0.608 mg, 3.53 mmol) and thionyl chloride (10 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by distillation. The crude acid chloride was cooled to room temperature, and then dissolved in THF (5 mL). 5-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (0.685 g, 2.72 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 2 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The tan solids were filtered to afford pure 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (0.760 g, 1.96 mmol, 72%).

後処理

  1. customThe thionyl chloride was then removed by distillation
  2. temperatureThe crude acid chloride was cooled to room temperature
  3. dissolutiondissolved in THF (5 mL)
  4. temperatureto reflux for 2 h
  5. temperatureto cool to room temperature
  6. customThe room temperature reaction mixture
  7. concentrationwas concentrated in vacuo
  8. dissolutionthe crude residue was dissolved in EtOH (5 mL)
  9. additionThe ethanolic solution was treated with 1M NaOH(aq) (2 mL)
  10. stirringstirred for 30 min
  11. customyielding a tan precipitate
  12. filtrationThe tan solids were filtered

出典と根拠

ORDレコード
ord-263239b6652d498e8aa0f8bb5280fac9
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

関連ノート

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