Piperazine → 2-Furan-2-yl-5-piperazin-1-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.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>CC#N>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:19]=[C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1Participants
Procedure
18 mmol of 2-furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (prepared as described in Caulkett et al., J. Chem. Soc. Perkin Trans I. 801-808 (1995)) was suspended in 50 mL of CH3CN along with 5 eq. of piperazine. The reaction 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 H2O, brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting crude product was purified by chromatography (95% CH2Cl2, 4% MeOH, 1% Et3N) to afford 2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine. 1H NMR (DMSO-d6) δ 8.2 (br s, 2H), 7.85 (d, J=1.0 Hz, 1H), 7.07 (d, J=3.6 Hz, 1H), 6.68 (dd, J=3.6 Hz. 1.0 Hz, 1H), 3.20-2.75 (m, 8H) ppm. MS: m/z=287 [M+H]+.
Workup
- temperatureunder reflux for 2 hours
- concentrationconcentrated under reduced pressure
- washwashed with H2O, brine
- dry with materialdried with Na2SO4
- concentrationconcentrated under reduced pressure
- customThe resulting crude product was purified by chromatography (95% CH2Cl2, 4% MeOH, 1% Et3N)
Sources & evidence
- ORD record
- ord-428d8a0221d24eeba187964f4285b08a
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285550B2
Reaction notes
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