Carbonyl heterocyclic compound and application thereof
A technology of heterocycles and compounds, applied in the field of carbonyl heterocycles, can solve problems such as lack of therapeutic agents
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Embodiment 1
[0292] Example 1: 6-(1H-benzo[d]imidazol-2-yl)-N-(3-(3-(3-(imidazo[1,2-a]pyridin-2-yl)benzene Formyl)-3-azabicyclo[3.1.0]hexane-6-yl)pyridineamide (L-1)
[0293]
[0294] One, the synthesis of 3-(imidazo[1,2-a]pyridin-2-yl)methyl benzoate
[0295]
[0296] At room temperature, 2-aminopyridine (1.6g, 17mmol), methyl 3-acetoformate (2.3g, 14mmol) and cuprous iodide (0.5g, 2.8mmol) were dissolved in 1,4-dioxane In 50 mL, the reaction solution was heated to reflux overnight, and monitored by LC-MS until the end of the reaction. After concentration under reduced pressure, 50 mL of water was added, extracted with ethyl acetate (50 mL x 3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a residue, which was subjected to column chromatography (eluent: petroleum ether / ethyl acetate =5 / 1) separated and purified to obtain a white solid (1.8g, 7.4mmol) with a yield of 52%. LC-MS: [M+1] + :253.09
[0297] ...
Embodiment 2
[0304] Example 2 6-(1H-benzo[d]imidazol-2-yl)-N-(3-(3-(3-(imidazo[1,2-a]pyridin-2-yl)benzyl Acyl)-3-azabicyclo[3.1.0]hexan-6-yl)pyridineamide (L-2)
[0305]
[0306] Under ice bath, mix 3-(imidazo[1,2-a]pyridin-2-yl)benzoic acid (0.12g, 0.5mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride (0.1g, 0.52mmol), 1-hydroxybenzotriazole (0.07g, 0.52mmol) and N, N-diisopropylethylamine (0.14g, 1.13mmol) were dissolved in N, In N-dimethylformamide 6mL, after stirring for 0.5h, add 6-(1H-benzo[d]imidazol-2-yl)-N-(3-azabicyclo[3.1.0]hexane-6- Base) pyridine amide (0.16g, 0.5mmol), continue to stir for 0.5 hours and return to room temperature to react overnight. The reaction solution was poured into 20 mL of water, extracted with ethyl acetate (20 mL x 3), washed with saturated brine, combined with organic phases, dried over anhydrous sodium sulfate, and concentrated under reduced pressure by silica gel column chromatography (DCM:MeOH=20:1) to obtain Off-white sol...
Embodiment 3
[0308] Example 3: (9-(3-(1h-benzo[d]imidazol-2-yl)benzoyl)-3,9-diazaspiro[5.5]undecane-3-yl)(3 -(Imidazol[1,2-a]pyridin-2-yl)phenyl)methanone (L-3)
[0309]
[0310] Under ice bath, mix 3-(imidazo[1,2-a]pyridin-2-yl)benzoic acid (0.12g, 0.5mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride (0.1g, 0.52mmol), 1-hydroxybenzotriazole (0.07g, 0.52mmol) and N, N-diisopropylethylamine (0.14g, 1.13mmol) were dissolved in N, In N-dimethylformamide 6mL, after stirring for 0.5h, add 6-(1H-benzo[d]imidazol-2-yl)-N-(3-azabicyclo[3.1.0]hexane-6- Base) pyridine amide (0.18g, 0.5mmol), continued to stir for 0.5 hours and returned to room temperature to react overnight. The reaction solution was poured into 20 mL of water, extracted with ethyl acetate (20 mL x 3), washed with saturated brine, combined with organic phases, dried over anhydrous sodium sulfate, and concentrated under reduced pressure by silica gel column chromatography (DCM:MeOH=20:1) to obtain Off-white ...
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