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

HRID 407726ノート

反応式

HRID 407726 の反応式
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][C:15]([F:19])([F:18])[CH2:16][NH2:17].CS(C)=O>O>[N+:11]([C:6]1[CH:7]=[C:8]2[CH2:9][N:17]([CH2:16][C:15]([F:19])([F:18])[F:14])[CH2:2][CH2:3][N:4]2[N:5]=1)([O-:13])=[O:12]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 575020831-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole

生成物 1

HCID 866839962-Nitro-5-(2,2,2-trifluoroethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine収率 78.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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), 2,2,2-trifluoroethanamine (594 mg, 6.0 mmol), and DMSO (5 mL), and 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 silical-gel column chromatography eluting with 50:1 dichloromethane/methanol to afford 134a (392 mg, 78%) as a yellow solid. MS-ESI: [M+H]+ 250.9

後処理

  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 silical-gel column chromatography
  8. washeluting with 50:1 dichloromethane/methanol

出典と根拠

ORDレコード
ord-2795cf80873d4004afadecdd50c73647
出典データセット
uspto-grants-2014_06
特許番号
US08754077B2

反応ノート

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