Water → 4-{4-Chloro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile

HRID 1625262노트

반응식

HRID 1625262 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14]2[NH:15][CH:16]=[CH:17][C:18](=O)[C:13]=2[C:12]([C:20]([F:23])([F:22])[F:21])=[N:11]1)[C:5]#[N:6].S(Cl)([Cl:26])=O.CN(C=O)C.O>C(Cl)(Cl)Cl>[Cl:26][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[N:10]([C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[CH3:1])[N:11]=[C:12]([C:20]([F:23])([F:22])[F:21])[C:13]=12

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1363901483-Methyl-4-{4-oxo-3-(trifluoromethyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile

생성물 1

HCID 675025754-{4-Chloro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile수율 71%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Compound (154d) (2.20 g) was dissolved in chloroform (14 mL), and thionyl chloride (1.00 mL) and DMF (0.148 mL) were added to the resulting solution, followed by reflux for 3 hr. Water was added to the reaction solution for distribution. The organic layer was washed with saturated sodium bicarbonate water. The organic layer after the washing was dried over anhydrous sodium sulfate, and the solvent was distilled away. 2-Propanol was added to the residue, and the precipitate was collected by filtration and then dried under reduced pressure to obtain compound (154e) (1.60 g, 71%).

후처리

  1. temperatureby reflux for 3 hr
  2. washThe organic layer was washed with saturated sodium bicarbonate water
  3. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. addition2-Propanol was added to the residue
  6. filtrationthe precipitate was collected by filtration
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-9fb95e0ba18d426b94cef799dd3431f8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779142B2

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