반응 #1259751

반응 방정식

4-chlorobenzyl chloride

Et3N

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

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

Et3N

→

title compound

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

용매

CH3CN

CH3CN

반응 조건

후처리

1. 1
   온도at reflux for 2 hours
2. 2
   농축concentrated
3. 3
   세척washed with brine
4. 4
   건조dried with Na2SO4
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThis material (1-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid tert-butyl ester) was dissolved in 2 mL of 25% TFA in CH2Cl2
7. 7
   농축It was then concentrated
8. 8
   기타The resulting reaction mixture
9. 9
   workup.STIRRINGwas stirred at room temperature for 18 hours
10. 10
    농축It was then concentrated
11. 11
    기타purified by preparative HPLC

실험 절차

Tert-butyl 2,7-diazabicyclo[3.3.0]octane-7-carboxylate (0.5 mmol; see U.S. Pat. No. 5,071,999) was added to a mixture of 2-furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.5 mmol, 1 eq.; see J. Chem. Soc. Perkin Trans. 1, 801 (1995)) and Et3N (0.6 mmol) in 5 mL of CH3CN. The reaction mixture was stirred at reflux for 2 hours. It was then cooled to room temperature and concentrated. The resulting residue was taken up in EtOAc, washed with brine, dried with Na2SO4, and concentrated under reduced pressure. This material (1-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid tert-butyl ester) was dissolved in 2 mL of 25% TFA in CH2Cl2 and allowed to stand at room temperature for 2 hours. It was then concentrated and the resulting residue was dissolved in 3 mL of CH3CN along with 0.5 mmol of 4-chlorobenzyl chloride and 0.8 mmol of Et3N. The resulting reaction mixture was stirred at room temperature for 18 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), 7.70 (d, J=1.0 Hz, 1H), 7.10 (d, J=3.6 Hz, 1H), 7.0-7.30 (m, 4H) 6.60 (dd, J=3.6, 1.0 Hz, 1H), 4.80 (brs, 2H), 2.30-3.8 (m, 10H). MS m/z: 438 [M+H]+.

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