Substituted tricyclic heterocyclic compounds and uses thereof
A technology for compounds and uses, applied in the field of tricyclic heterocyclic compounds, for the treatment of conditions caused by cancer and neurodegenerative diseases, capable of addressing problems such as hyperphosphorylation
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Embodiment 1
[0368]
[0369] step 1
[0370] Synthesis of 4-chloro-3-iodine-1H-pyrazole [4,3-C] pyridine (intermediate 1):
[0371]
[0372] At room temperature, iodine (19 g, 76 mmol) was added to 4-chloro-1H-pyrazole [4,3-C] pyridine (5.8 g, 38 mmol, synthesized according to WO 201010633 A1 and WO 2012038743 A1) and KOH (8g, 142 mmol) The mixture in 1,4-dioxane (100 mL). The reaction mixture was stirred at 75 ° C for 4 hours, then cooled to room temperature. Tissue solution Na 2 S 2 O 3 (Aqueous solution) diluted, filtered the resulting precipitate and dried to give a yellow solid (4.1 g). The filtrate was allowed to stand for 3 days, and the resulting precipitate was filtered to produce an additional 3.55 g of a product. The yield (7.65 g, 72%). 1 H NMR (400MHz, CDCL 3 ΔPPM7.65 (D, J = 6.0 Hz, 1H), 8.13 (D, J = 6.0 Hz, 1H), 14.22 (S, 1H) .M / Z (ESI) + : 280 [M + H] +
[0373] Step 2
[0374] Synthesis 1- (4-methoxybenzyl) -4-chloro-3-iodine-1H-pyrazole [4,3-C] pyridine (intermediate 2...
Embodiment 2-14
[0402] Example 2-14 is prepared from the first embodiment by using a suitable amine in step 3.
[0403]
[0404]
[0405]
Embodiment 15
[0407] In step 4, methyl methacrylate was used for methyl methacrylate, and Example 15 was prepared in Example 14.
[0408]
[0409]
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