1H-1,2,4-Triazole → (S)-2-(2-(3-(1H-1,2,4-triazol-1-yl)phenyl)-1H-imidazol-1-yl)-6a-ethyl-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-one

(S)-2-(2-(3-bromophenyl)-1H-imidazol-1-yl)-6a-ethyl-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-one (Example 252, 0.118 mmol, 0.050 g) was added to a solution of 1,2,4-triazole (0.593 mmol, 0.041 g), copper iodide (0.007 mmol, 0.001 g), N1,N2-dimethylcyclohexane-1,2-diamine (0.023 mmol, 0.003 g), and Cs2CO3 (0.593 mmol, 0.193 g) in 1 mL of DMA. The reaction mixture was microwaved at 185° C. for 1 h. The reaction mixture was diluted with 15 mL of DCM, washed with 5 mL of water, dried with Na2SO4, filtered and concentrated. The resulting residue was purified by reverse phase HPLC to give the title compound as a white solid (0.012 g, 23%); 1H NMR (400 MHz, CDCl3) δ: 8.83 (s, 1H), 8.12 (m, 2H), 7.95 (s, 1H), 7.90 (m, 1H), 7.69 (s, 1H), 7.60 (m, 3H), 3.37 (m, 4H), 3.20 (m, 1H), 2.35 (m, 1H), 2.26 (m, 3H), 2.00 (m, 2H), 1.77 (m, 1H), 1.62 (m, 1H), 0.78 (t, J=7.4 Hz, 3H); LCMS: 442.3 m/z (M+H)+; ret. Time: 4.722 min (Analytical Method C).

1. customThe reaction mixture was microwaved at 185° C. for 1 h
2. washwashed with 5 mL of water
3. dry with materialdried with Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe resulting residue was purified by reverse phase HPLC

ORD 기록

ord-cf0a866db12845c79967db5ebae7acb5

출처 데이터셋

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08541418B2