2,5-Diazabicyclo[2.2.1]heptane → 5-(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:19]=[C:9]2[N:10]=[C:11](S(C)(=O)=O)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1.[CH:20]12[CH2:26][CH:23]([NH:24][CH2:25]1)[CH2:22][NH:21]2>CC#N>[CH:20]12[CH2:26][CH:23]([NH:24][CH2:25]1)[CH2:22][N:21]2[C:11]1[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:19]=[C:9]2[N:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.7 mmol, 1 eq.; see J. Chem. Soc. Perkin Trans. 1, 801 (1995)) and 2,5-diaza-bicyclo[2.2.1]heptane (5 eq.) were suspended in 10 mL of CH3CN. The mixture was stirred under reflux for 2 hours. It was then cooled to room temperature and concentrated under reduced pressure. The residue was taken up in CH2Cl2 and washed with water, brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting crude product was purified by column chromatography (95% CH2Cl2, 4% MEOH, 1% Et3N) to afford 5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine.
Workup
- temperatureunder reflux for 2 hours
- concentrationconcentrated under reduced pressure
- washwashed with water, brine
- dry with materialdried with Na2SO4
- concentrationconcentrated under reduced pressure
- customThe resulting crude product was purified by column chromatography (95% CH2Cl2, 4% MEOH, 1% Et3N)
Sources & evidence
- ORD record
- ord-d278318a0b974579b4a3a2b6c361627e
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834014B2
Reaction notes
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