Ammonium Chloride → 3-cyclopropyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine

HRID 79388

Reaktionsgleichung

[CH:1]1([C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[N+:13]([O-])=O)[N:6]([CH2:16][C:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=3)[N:5]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH:1]1([C:4]2[C:12]3[C:11]([NH2:13])=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]([CH2:16][C:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=3)[N:5]=2)[CH2:2][CH2:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a suspension of 3-cyclopropyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (7.55 g, 24.3 mmol) in EtOH/H2O (70 mL/15 mL) was added iron powder (27.1 g, 485 mmol) and NH4Cl (1.30 g, 24.3 mmol). The reaction mixture was heated to reflux for 3 hours. The mixture was cooled to 60° C. and filtered through a pad of Celite washing with a 20:1 EtOH/Et3N (300 mL) and 1:1 MeOH/DCM (300 mL). The filtrate was concentrated under reduced pressure. The residue was dissolved in EtOAc (300 mL), washed with saturated NaHCO3 solution, dried (Na2SO4) and concentrated under reduced pressure to give the product (7.1 g).

Aufarbeitung

temperatureThe reaction mixture was heated
temperatureto reflux for 3 hours
filtrationfiltered through a pad of Celite
washwashing with a 20:1 EtOH/Et3N (300 mL) and 1:1 MeOH/DCM (300 mL)
concentrationThe filtrate was concentrated under reduced pressure
dissolutionThe residue was dissolved in EtOAc (300 mL)
washwashed with saturated NaHCO3 solution
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-6b42dcc393e94733ab63114fcc4f6fb2
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841455B2

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