Dimethyl Sulfoxide → 5-(3-Methoxypropyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 593113ノート

反応式

HRID 593113 の反応式
Br[CH2:2][CH2:3][N:4]1[C:8]([CH2:9]Cl)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.[CH3:14][O:15][CH2:16][CH2:17][CH2:18][NH2:19].CS(C)=O>C(OCC)(=O)C>[CH3:14][O:15][CH2:16][CH2:17][CH2:18][N:19]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

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 16723-MethoxypropylamineHCID 866845401-(2-Bromoethyl)-5-(chloromethyl)-3-nitro-1H-pyrazole

生成物 1

HCID 866845565-(3-Methoxypropyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine収率 66.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A microwave vial equipped with a magnetic stirrer was charged with 1-(2-bromoethyl)-5-(chloromethyl)-3-nitro-1H-pyrazole 296c (600 mg, 2.2 mmol), 3-methoxypropan-1-amine (595 mg, 6.6 mmol), and DMSO (6 mL). It was heated at 120° C. under microwave irradiation for 0.5 h. The mixture was then cooled to room temperature and diluted with ethyl acetate (30 mL). The resulting mixture was washed with water (3×10 ml). The organic layer was dried and filtered. The filtrate was concentrated under pressure and the residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 309a (350 mg, 66%) as a yellow solid. MS-ESI: [M+H]+ 241.1

後処理

  1. customA microwave vial equipped with a magnetic stirrer
  2. temperatureThe mixture was then cooled to room temperature
  3. washThe resulting mixture was washed with water (3×10 ml)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under pressure
  7. customthe residue was purified by silica-gel column chromatography
  8. washeluting with 30:1 dichloromethane/methanol

出典と根拠

ORDレコード
ord-5cb7072882d64911902de754bc7488c9
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

読み込み中…