Nitrogen → 2-(2-Methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-[1,2,3]triazol-2-ylmethyl)-pyridine

HRID 42786

Reaktionsgleichung

N#N.[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH2:15]OS(C)(=O)=O)[CH:12]=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[N+:21]([C:24]1[CH:28]=[N:27][NH:26][N:25]=1)([O-:23])=[O:22].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[CH3:3][C:4]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH2:15][N:26]3[N:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]3)[N:14]=2)[O:5][CH2:6][CH2:7][O:8]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester (164 mg, 0.6 mmol) in DMF (2.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (57 mg, 0.5 mmol) in DMF (1.0 mL) pre-treated for 30 min with DIPEA (0.20 mL, 1.17 mmol) and the reaction mixture was stirred for 48 h at 50° C. Water (10 mL), followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 to 1:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (1:1 hept-EA)=0.50. LC-MS-conditions 02: tR=0.90 min, [M+H]+=292.35.

Aufarbeitung

additionwere added
extractionThe aq. layer was extracted with EA (10 mL)
dry with materialextracts were dried over Na2SO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (4:1 to 1:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag: ord-8a3e03d2364f443ebcc2de91fd55fb59
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536209B2

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