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

HRID 1022173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022173
[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

Komponenten

6

Edukt 2

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

Produkt 1

HCID 580437871-Methyl-5-((methyl(oxetan-3-yl)amino)methyl)-1H-pyrazol-3-amineAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ec5c968fa4bf4944bf5fb0c5f5ead353
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716274B2

Notizen zur Reaktion

Wird geladen…