Imidazol[4,5-c]pyridine-7-carboxamide derivative, its preparation method and medical application
A C5-C7, pharmacy technology, applied in the field of medicinal chemistry
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Examples
Embodiment 1
[0035] Synthesis of 4,5-diaminonicotinamide (b)
[0036] Add 5.0 g of 4-amino-5-nitronicotinamide to 100 ml of methanol in a 50 ml one-necked flask, add 0.25 g of 10% Pd-C, and hydrogenate at normal temperature and pressure. TLC tracking detection, after the reaction of the raw materials was complete, the hydrogenation was stopped, suction filtered, and the filtrate was spin-dried to obtain 3.6 g of a yellow solid with a yield of 85.7%.
Embodiment 2
[0038] Synthesis of 2-(N-Cbz-2-pyrrolyl)-7-carboxamidoimidazo[4,5-c]pyridine (d-1)
[0039] In a 100ml three-neck flask, dissolve N-Cbz proline (3.6g, 14.4mmol) in 50ml of dichloromethane, add 5.0ml of thionyl chloride, and heat to reflux. After reacting for 2 h, the solvent was distilled off, and the residue was dissolved in 50 ml of tetrahydrofuran for use.
[0040]Add 4,5-diaminonicotinamide (1.0g, 6.58mmol) into a 50ml three-necked flask and dissolve it in 10ml of DMF, add 1.2ml of pyridine, add the tetrahydrofuran solution of the above acid chloride dropwise under ice bath, and add dropwise After the completion, place it at room temperature and stir overnight. After the reaction of the raw materials is detected by TLC, the tetrahydrofuran and pyridine are evaporated under reduced pressure, and the residue is poured into ice water under heat. 2 CO 3 The pH value of the solution was adjusted to be alkaline, and a solid precipitated out. The solid was filtered, washed with...
Embodiment 3
[0044] Synthesis of 2-(2-pyrrolyl)-7-carboxamide imidazo[4,5-c]pyridine (e-1)
[0045] Add 2-(N-Cbz-2-pyrrolyl)-7-carboxamide imidazol[4,5-c]pyridine (1.0g, 2.7mmol) into 20ml of methanol in a 50ml one-necked flask, add 0.1g10 %Pd-C, hydrogenated under normal temperature and pressure. TLC tracking detection, after the reaction of the raw materials was complete, the hydrogenation was stopped, suction filtered, and the filtrate was spin-dried to obtain 0.56 g of white solid, yield: 90.0%. Melting point: 120-122°C.
[0046] 1 H-NMR(300MHz,DMSO),δ(ppm):8.87(s,1H),8.75(s,1H),7.75(s,1H),4.57(dd,J 1 =8.0Hz,J 2 =6.2Hz,1H),4.04(m,2H),2.27(m,1H),2.03(m,1H),1.93(m,2H)
[0047] MS(ESI(+)70V)m / z:232[M+H] + .
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