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

HRID 42787

Reaktionsgleichung

N#N.[CH3:3][C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[N: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[N: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 mixture of 2-(2-methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-[1,2,3]triazol-2-ylmethyl)-pyridine (66 mg, 0.23 mmol), iron powder (38 mg, 0.68 mmol) and NH4Cl (61 mg, 1.13 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 1 h. 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 pale green oil: TLC: rf (EA)=0.50. LC-MS-conditions O2: tR=0.67 min; [M+H]+=262.40.

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-28ae2099424942588fc09a82d8d1ba37
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536209B2

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