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

HRID 1022164ノート

反応式

HRID 1022164 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][CH:17]([NH2:19])[CH3:18].CS(C)=O>O>[CH3:14][O:15][CH2:16][CH:17]([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)[CH3:18]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 123458MethoxyisopropylamineHCID 866845401-(2-Bromoethyl)-5-(chloromethyl)-3-nitro-1H-pyrazole

生成物 1

HCID 866845445-(1-Methoxypropan-2-yl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine収率 68%

試薬・触媒・溶媒 1

HCID 962Water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 (1.0 g, 3.7 mmol), 1-methoxypropan-2-amine (1.0 g, 11.2 mmol), and DMSO (6 mL). The mixture was heated at 120° C. under microwave irradiation for 1.0 h. It was the cooled to room temperature and diluted with water (30 mL). The resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (60/1 to 1/1) to afford 300a (600 mg, 68%) as a yellow solid. MS-ESI: [M+H]+ 241.0

後処理

  1. customA microwave vial equipped with a magnetic stirrer
  2. temperaturecooled to room temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×20 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography
  7. washeluting with petroleum ether/ethyl acetate (60/1 to 1/1)

出典と根拠

ORDレコード
ord-9543b2bc21f84f6fa8469a43e6531d96
出典データセット
uspto-grants-2014_05
特許番号
US08716274B2

反応ノート

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