تفاعل #327966

معادلة التفاعل

water

sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate

suspension

2-(dimethylamino)-N-(5-ethynyl-1H-indazol-3-yl)acetamide

1-(azidomethyl)-3-methylbenzene

→

title compound

N2,N2-dimethyl-N1-{5-[1-(3-methylbenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-yl}glycinamide

المذيبات

tert-butanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed under reduced pressure
2. 2
   أخرىthe residue was purified by reverse phase
3. 3
   غسيلacetonitrile/water (0.05 M ammonium acetate) gradient elution method

الإجراء التجريبي

To a suspension of Example 282E (0.16 g, 0.660 mmol) in tert-butanol (1.2 mL) was added 1-(azidomethyl)-3-methylbenzene (0.098 g, 0.667 mmol), then water (1.2 mL). A solution of sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (0.057 mL, 0.066 mmol, 1.6 M in water) and an aqueous solution of copper (II) sulfate pentahydrate (0.019 mL, 6.6 μmol, 0.34M) was added. The reaction mixture was heated at about 60° C. for about 2 hours. The solvent was removed under reduced pressure and the residue was purified by reverse phase HPLC using acetonitrile/water (0.05 M ammonium acetate) gradient elution method to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.77 (s, 1H), 10.05 (s, 1H), 8.56 (s, 1H), 8.24 (s, 1H), 7.82 (d, 1H, J=8.6), 7.50 (d, 1H, J=8.8), 7.28 (t, 1H, J=7.6), 7.16 (m, 4H), 5.59 (s, 2H), 3.18 (s, 2H), 2.34 (s, 6H), 2.30 (s, 3H). MS (ESI+) m/z 390.3 (M+H)+.

المصدر