Thionyl Chloride → HCID 86610406, 화합물

HRID 640952

반응식

HRID 640952 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 86610406HCID 86610406, 화합물수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
79 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bc8c4e9bcb4244c2a49a0e84ea73097c
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

연결된 노트

불러오는 중…