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

HRID 1022173노트

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HRID 1022173 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

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온도
70 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-ec5c968fa4bf4944bf5fb0c5f5ead353
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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