Reaktion #1259752

Reaktionsgleichung

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

Lösungsmittel

CH3CN

EtOAc

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine
2. 2
   Trocknendried with Na2SO4
3. 3
   Einengenconcentrated 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
   EinengenIt was then concentrated to dryness
7. 7
   workup.STIRRINGThe reaction mixture was stirred
8. 8
   Temperaturat reflux for 3 hours
9. 9
   EinengenIt was then concentrated
10. 10
    Sonstigepurified by preparative HPLC

Vorschrift

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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