Heterocyclic compounds and inhibitors of p27kip1 breakdown
A compound and therapeutic agent technology, applied in the field of heterocyclic compounds and p27Kip1 decomposition inhibitors, can solve problems such as undocumented relationships
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Embodiment 1-1
[0324] Step 1-1-1
[0325] Ethyl 4-fluoro-3-nitrobenzoate
[0326] [chem 30]
[0327]
[0328] Suspend 4-fluoro-3-nitrobenzoic acid (150g, 0.810mol) in ethanol (1000ml), add concentrated sulfuric acid (25ml) dropwise, and heat to reflux for 8 hours. After standing to cool, it was concentrated under reduced pressure, and water was added with stirring. The precipitate was separated by filtration, washed with water and ventilated to dry to obtain the title compound (160 g, 93%) as a yellow solid.
[0329] 1 H-NMR (DMSO-d 6 ) δ: 8.56 (dd, J=2.3, 7.3Hz, 1H), 8.35-8.31 (m, 1H), 7.76-7.71 (m, 1H), 4.37 (q, J=7.3Hz, 2H), 1.35 (t , J=7.3Hz, 3H).
[0330] Mass spectrum, m / z: 213 (M + ), 185, 168 (base peak).
[0331] Step 1-1-2
[0332] 4-Methylamino-3-nitrobenzoic acid ethyl ester
[0333] [chem 31]
[0334]
[0335] Dissolve ethyl 4-fluoro-3-nitrobenzoate (10.0 g, 46.9 mmol) prepared in the above step 1-1-1 in methanol (40 ml), add triethylamine (10 ml, 70.4 mmol), an...
Embodiment 1-2~1-6
[0360] Instead of the 40% methylamine-methanol solution as the ring-forming component, or ethyl 4-fluoro-3-nitrobenzoate as the monocyclic compound, the compounds shown in the table below were used. 1-1 is operated in the same way to obtain the target bicyclic compound.
[0361] [Table 9]
[0362] Table 9
[0363]
[0364] Synthetic route 2
[0365] [chem 35]
[0366]
[0367] (In the formula, R represents an alkyl group, and R' represents an alkyl or alkoxyalkyl group)
Embodiment 2-1
[0369] Step 2-1-1
[0370] 1,2-Dimethyl-1H-benzimidazole-5-carboxylic acid ethyl ester
[0371] [chem 36]
[0372]
[0373] Ethyl 3-amino-4-methylaminobenzoate (1.00 g, 5.15 mmol) prepared in step 1-1-3 was dissolved in acetic anhydride (4 ml), and heated under reflux for 19 hours. After standing to cool, it was neutralized with saturated sodium bicarbonate solution, and extracted with ethyl acetate. Dry over anhydrous magnesium sulfate, then concentrate. Purification by silica gel column chromatography (chloroform:methanol=10:1) gave the title compound (1.15 g, quantitative) as a light brown oil.
[0374] 1 H-NMR (CDCl 3 ) δ: 8.39 (d, J=1.5Hz, 1H), 7.98 (dd, J=1.5, 8.5Hz, 1H), 7.28 (d, J=8.5Hz, 1H), 4.39 (q, J=6.9Hz, 2H), 3.75 (s, 3H), 2.62 (s, 3H), 1.41 (t, J=6.9Hz, 3H).
[0375] Mass spectrum, m / z: 218 (M + ), 173 (base peak).
[0376] Step 2-1-2
[0377] (1,2-Dimethyl-1H-benzimidazol-5-yl)methanol
[0378] [chem 37]
[0379]
[0380] Using ethyl 1,2-dimet...
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