Methyl triflate → HCID 178448620, 화합물

HRID 883024

반응식

HRID 883024 반응식
[CH2:1]([N:5]1[C:9]([NH:10][C:11](=[O:23])[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[F:22])=[CH:8][C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])=[N:6]1)[CH2:2][CH2:3][CH3:4].F[C:29](F)(F)S(OC)(=O)=O.[NH4+].[OH-]>C1(C)C=CC=CC=1.O.CC(C)=O>[CH2:1]([N:5]1[N:6]([CH3:29])[C:7]([C:24]([CH3:26])([CH3:25])[CH3:27])=[CH:8]/[C:9]/1=[N:10]\[C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:15]=[CH:14][C:13]=1[F:22])[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 3

HCID 9526Methyl triflateHCID 14923Ammonium HydroxideHCID 66643255n-(1-Butyl-3-tert-butyl-1h-pyrazol-5-yl)-2-fluoro-5-(trifluoromethyl)benzamide

생성물 1

HCID 178448620HCID 178448620, 화합물수율 89.2%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of Example 4B (50.2 g, 130 mmol) in toluene (500 mL) was added methyl trifluoromethanesulfonate (21.4 mL, 195 mmol). The mixture was warmed to 100° C. and stirred for 20 hours. The mixture was cooled to ambient temperature then diluted with water (200 mL) and acetone (500 mL). This solution was stirred for 30 minutes then concentrated NH4OH (100 mL) was added. The mixture was stirred for 30 minutes then partially concentrated under reduced pressure. The residue was diluted with EtOAc (300 mL) and brine (100 mL), the layers were separated and the aqueous phase was extracted with EtOAc (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 80% hexanes/EtOAc to 100% EtOAc to 10% MeOH in EtOAc) and the fractions collected and concentrated. The material was then dissolved in EtOAc (150 mL) and was washed with 10% NaOH (100 mL). The layers were separated, the aqueous phase was extracted with EtOAc (3×50 mL) and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give (46.3 g, 116 mmol, 89% yield) the title compound. MS (ESI+) m/z 400 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringThis solution was stirred for 30 minutes
  3. stirringThe mixture was stirred for 30 minutes
  4. concentrationthen partially concentrated under reduced pressure
  5. additionThe residue was diluted with EtOAc (300 mL) and brine (100 mL)
  6. customthe layers were separated
  7. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
  8. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography (SiO2, 80% hexanes/EtOAc to 100% EtOAc to 10% MeOH in EtOAc)
  12. customthe fractions collected
  13. concentrationconcentrated
  14. dissolutionThe material was then dissolved in EtOAc (150 mL)
  15. washwas washed with 10% NaOH (100 mL)
  16. customThe layers were separated
  17. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  18. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  19. filtrationfiltered
  20. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bf160eab9f8840e09caa881af15bf39b
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236822B2

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