Dimethyl Sulfoxide → 5-(2,2-Difluoroethyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 407731노트

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HRID 407731 반응식
Br[CH2:2][CH2:3][N:4]1[C:8]([CH2:9]Br)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.[F:14][CH:15]([F:18])[CH2:16][NH2:17].CS(C)=O>O>[F:14][CH:15]([F:18])[CH2:16][N:17]1[CH2:2][CH2:3][N:4]2[N:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[C:8]2[CH2:9]1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 1362742,2-DifluoroethanamineHCID 575020831-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole

생성물 1

HCID 866840025-(2,2-Difluoroethyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine수율 80%

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

A sealed tube equipped with a magnetic stirrer was charged with 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole 124c (632 mg, 2.0 mmol), 2,2-difluoroethanamine (486 mg, 6.0 mmol), and DMSO (5 mL). It was heated at 120° C. for 2 h. The mixture was cooled to room temperature and diluted with water (20 mL). The resulting mixture was extracted with ethyl acetate (3×20 mL). The combiner organic layer was dried and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 50:1 dichloromethane/methanol to afford 135a (371 mg, 80%) as a yellow solid. MS-ESI: [M+H]+ 233.2

후처리

  1. customA sealed tube equipped with a magnetic stirrer
  2. temperatureThe mixture was cooled to room temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×20 mL)
  4. customThe combiner organic layer was dried
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica-gel column chromatography
  8. washeluting with 50:1 dichloromethane/methanol

출처 및 근거

ORD 기록
ord-a7b68e68763b40aab099e19ec531a70a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754077B2

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