Ammonium Chloride → 1-Methyl-5-((methyl(oxetan-3-yl)amino)methyl)-1H-pyrazol-3-amine

HRID 1022173ノート

反応式

HRID 1022173 の反応式
[CH3:1][N:2]([CH2:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)[CH:3]1[CH2:6][O:5][CH2:4]1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[CH3:13][N:12]1[C:8]([CH2:7][N:2]([CH3:1])[CH:3]2[CH2:4][O:5][CH2:6]2)=[CH:9][C:10]([NH2:14])=[N:11]1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 58043818N-Methyl-N-((1-methyl-3-nitro-1H-pyrazol-5-yl)methyl)oxetan-3-amine

生成物 1

HCID 580437871-Methyl-5-((methyl(oxetan-3-yl)amino)methyl)-1H-pyrazol-3-amine収率 83.2%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a solution of 302b (1.8 g, 7.96 mmol) in ethanol (20 mL) and water (20 mL), NH4Cl (3.3 g, 63.6 mmol) and iron powder (1.80 g, 31.8 mmol) were added. The reaction mixture was heated at 70° C. for 2 h. After that, the mixture was cooled to room temperature and filtered. The filtrate was evaporated and the residue was extracted with methylene chloride (3×30 mL), dried Na2SO4, and concentrated to afford the crude product, which was purified on flash column eluting with 50:1 methylene chloride/methanol containing 0.5% triethylamine to afford 302c as a yellow oil (1.3 g, 83%). LCMS: (M+H)+ 197

後処理

  1. temperatureAfter that, the mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. extractionthe residue was extracted with methylene chloride (3×30 mL), dried Na2SO4
  5. concentrationconcentrated
  6. customto afford the crude product, which
  7. customwas purified on flash column
  8. washeluting with 50:1 methylene chloride/methanol containing 0.5% triethylamine

出典と根拠

ORDレコード
ord-ec5c968fa4bf4944bf5fb0c5f5ead353
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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