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2-furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Et3N

Tert-butyl 2,7-diazabicyclo[3.3.0]octane-7-carboxylate

2,6-dichlorobenzyl chloride

Et3N

→

title compound

5-[1-(2,6-Dichloro-benzyl)-hexahydro-pyrrolo[3,4-b]pyrrol-5-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

용매

CH3CN

EtOAc

CH3CN

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후처리

1. 1
   세척washed with brine
2. 2
   건조dried with Na2SO4
3. 3
   농축concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe resulting residue was dissolved in 2 mL of 25% TFA in CH2Cl2
5. 5
   workup.WAITto stand at room temperature for 3 hours
6. 6
   농축It was then concentrated to dryness
7. 7
   workup.STIRRINGThe reaction mixture was stirred
8. 8
   온도at reflux for 3 hours
9. 9
   농축It was then concentrated
10. 10
    기타purified by preparative HPLC

실험 절차

Tert-butyl 2,7-diazabicyclo[3.3.0]octane-7-carboxylate (0.3 mmol; see U.S. Pat. No. 5,071,999) dissolved in 2 mL of CH3CN along with 0.3 mmol of 2,6-dichlorobenzyl chloride and 0.5 mmol of Et3N. The reaction mixture was stirred at room temperature for 18 hours. It was then diluted with EtOAc, washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was dissolved in 2 mL of 25% TFA in CH2Cl2 and allowed to stand at room temperature for 3 hours. It was then concentrated to dryness. The resulting residue was dissolved in 3 mL of CH3CN along with 0.3 mmol of 2-furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (see J. Chem. Soc. Perkin Trans. 1, 801 (1995)) and 0.8 mmol of Et3N. The reaction mixture was stirred at reflux for 3 hours. It was then concentrated and purified by preparative HPLC to afford the title compound. 1H NMR (400 Hz, DMSO-d6) δ 8.20 (brs, 1H), 7.8 (d, J=1.0 Hz, 1H), 7.30 (d, J=3.6 Hz, 1H), 7.1-7.30 (m, 3H) 6.60 (dd, J=3.6, 1.0 Hz, 1H), 4.80 (brs, 2H), 2.30-3.8 (m, 10H). MS m/z: 472 [M+H]+.

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