Thionyl Chloride → HCID 86610406、化合物

HRID 640952

反応式

HRID 640952 の反応式
[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]([OH:10])=O.S(Cl)(Cl)=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[C:19]([C:21]1[CH:29]=[C:28]2[C:24]([CH2:25][C:26](=[O:30])[NH:27]2)=[CH:23][CH:22]=1)=[O:20]>C1COCC1>[O:30]=[C:26]1[CH2:25][C:24]2[C:28](=[CH:29][C:21]([C:19]([C:18]3[CH:17]=[C:16]([NH:15][C:8]([C:3]4[N:4]([CH3:7])[N:5]=[CH:6][C:2]=4[Cl:1])=[O:10])[CH:33]=[CH:32][CH:31]=3)=[O:20])=[CH:22][CH:23]=2)[NH:27]1

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 6708234-chloro-1-methyl-1H-pyrazole-5-carboxylic acidHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

生成物 1

HCID 86610406HCID 86610406、化合物収率 84%

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 4-Chloro-2-methyl-2H-pyrazole-3-carboxylic acid (0.139 g, 0.873 mmol) and thionyl chloride (5 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by concentration in vacuo. The crude acid chloride was cooled to room temperature, and then dissolved in THF (5 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.200 g, 0.794 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 tan solids were filtered and washed with ˜3 mL of THF to afford the pure 4-Chloro-2-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.264 g, 0.667 mmol, 84%).

後処理

  1. customThe thionyl chloride was then removed by concentration in vacuo
  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. filtrationThe tan solids were filtered
  7. washwashed with ˜3 mL of THF

出典と根拠

ORDレコード
ord-bc8c4e9bcb4244c2a49a0e84ea73097c
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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