Nitrogen → 1-[6-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl]-1H-pyrazol-4-ylamine

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Reaktionsgleichung

N#N.[CH3:3][C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[N:17]3)[N:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:15][N:16]3[CH:20]=[C:19]([NH2:21])[CH:18]=[N:17]3)[CH:12]=[CH:13][CH:14]=2)[O:8][CH2:7][CH2:6][O:5]1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a 0.1M solution of 2-(2-methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-pyrazol-1-ylmethyl)-pyridine (145 mg, 0.50 mmol), iron powder (84 mg, 1.50 mmol) and NH4Cl (135 mg, 2.50 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 30 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (20 mL) was added followed by 1N NaOH (20 mL). The aq. layer was extracted with CH2Cl2 (2×20 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a deep red oil. LC-MS-conditions 02: tR=0.56 min; [M+H]+=261.61.

Aufarbeitung

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
additionCH2Cl2 (20 mL) was added
extractionThe aq. layer was extracted with CH2Cl2 (2×20 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-da875732ca6e4a119eb6f40ecc12f5db
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08288419B2

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