Heterocyclic Janus kinase 3 inhibitors
A kind of technology of heterocycloalkyl and heteroaryl, applied in the field of immunological disease therapeutic agents, can solve the problems such as no specific disclosed compounds
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preparation example 1
[0163] According to a method similar to the method described in Example 1 using the corresponding starting compounds, the compounds in Preparation Examples 1-1 to 1-25 shown in the table below were prepared.
[0164] Table 2
[0165]
[0166] Table 2 (continued)
[0167]
[0168] Table 2 (continued)
[0169]
[0170] table 3
[0171] Preparation example
[0172] Table 3 (continued)
[0173] Preparation example
[0174] 1-9
preparation example 2
[0176] 3-(4-Chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,2,4-oxadiazole-5-carboxylic acid ethyl ester (60mg) in 1-methyl - A solution of 2-pyrrolidone (0.6ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.092ml) was added to glycinamide hydrochloride (34mg) , and the resulting mixture was stirred at 70 °C for 1 h. After standing to cool, with preparative HPLC (10mM NH 4 HCO 3 +NH 3 (pH=9.2)=90:10 to 20:80) directly purify the reaction solution. The active fraction was concentrated and dried to give 3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-N-methyl-1,2,4-oxadiazole - 5-Carboxylate (23 mg) as a solid.
[0177] According to a method similar to the method described in Example 2 using the corresponding starting compounds, the compounds in Preparation Examples 2-1 to 2-26 shown in the table below were prepared.
[0178] Table 4
[0179]
[0180] Table 4 (continued)
[0181]
[0182] Table 4 (continued)
[0183]
[0184] table 5
[0185]
preparation example 3
[0187]Benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (55mg), ethyl {[(4-amino-1-adamantyl)carbonyl]amino}acetate (54mg ) and triethylamine (80 μl) were dissolved in N-methyl-2-pyrrolidone (0.55 ml), and stirred at 180° C. for 1 hour using a microwave reaction system. Ethyl acetate and water were added to the resulting reaction liquid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate), the obtained compound was dissolved in dioxane (1.1ml) and methanol (1.1ml), and 10% palladium-carbon (50% wet), and the catalytic reduction reaction was carried out at ambient temperature and 1 atmospheric pressure for 4 hours. Methanol, dioxane, and 1M hydrochloric acid were added, and the precipitated solid was dissolved and filtered to remove the catalyst. The filtrate was conce...
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