6-pyridin benzimidazole indole derivatives and preparation method thereof, and application of 6-pyridin benzimidazole indole derivatives in field of medicine
A technology of indole derivatives and benzimidazoles, which is applied in the field of 6-pyridine benzimidazole indole derivatives, can solve problems such as restriction, agonism, and metabolic instability
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Embodiment 1
[0028] 2-(4-((2-n-propyl-4-methyl-6-(pyridin-2-yl)benzimidazolyl)methyl)-1H-indol-1-yl)benzoic acid (Compound Ib ) preparation method specifically comprises the following steps:
[0029] Step 1: Synthesis of N-o-cyanophenyl-1H-indole-4-carbaldehyde (compound V):
[0030]
[0031] Dissolve 1H-indole-4-carbaldehyde (10.00g, 68.97mmol) in N,N-dimethylformamide (150mL), add o-fluorobenzonitrile (8.40mL, 75.86mmol) and potassium carbonate (19.03g , 137.94 mmol). The mixture was stirred and refluxed at 160° C. for about 2 h, and monitored by TLC until the reaction was complete. After the temperature of the reaction solution was lowered to room temperature, it was filtered, and the filter cake was washed three times with dichloromethane (20 mL). 200 mL of dichloromethane and 200 mL of water were added to the filtrate, and the organic phase was separated; the aqueous phase was extracted with dichloromethane (150 mL×3), and the organic phases were combined. The organic phase was...
Embodiment 2
[0045] 2-(4-((2-n-propyl-4-methyl-6-(pyridin-2-yl)benzimidazolyl)methyl)-1H-indol-1-yl)benzoic acid (Compound Ib ) preparation method specifically comprises the following steps:
[0046] Step 1: Synthesis of N-o-carboxyphenyl-4-hydroxymethyl-1H-indole (compound X):
[0047]
[0048] Dissolve N-o-cyanophenyl-4-hydroxymethyl-1H-indole (10g, 40.32mmol) in ethylene glycol (100mL), slowly add 5M sodium hydroxide (80mL) solution dropwise, after the addition is complete Stir at reflux. After the completion of the reaction as monitored by TLC, cool to room temperature, add 5M hydrochloric acid (about 80 mL) solution under ice bath to adjust the pH to 5-7, extract three times with dichloromethane (100 mL×3), and combine the organic phases. The organic phase was washed with saturated brine (100 mL×3), dried over anhydrous magnesium sulfate, filtered, and the organic phase was evaporated under reduced pressure to obtain a pale yellow solid. The solid was recrystallized to obtain ab...
Embodiment 3
[0059] 2-(4-((2-ethyl-4-methyl-6(pyridin-2-yl)benzimidazolyl)methyl)-1H-indol-1-yl)benzoic acid (compound Ia) Preparation:
[0060] The synthesis method is as described in Example 1 and Example 2. 1 H NMR (400MHz, DMSO): δ12.92(s, 1H), 8.59(d, J=4.7Hz, 1H), 8.06(s, 1H), 7.99-7.91(m, 2H), 7.84-7.81(m , 2H), 7.74(t, J=7.6Hz, 1H), 7.61-7.51(m, 3H), 7.32-7.20(m, 1H), 7.06-6.95(m, 2H), 6.72(d, J=3.2 Hz, 1H), 6.41-6.30(m, 1H), 5.87(s, 2H), 2.85(q, J=7.4Hz, 2H), 2.65(s, 3H), 1.29(t, J=7.5Hz, 3H ). 13 C NMR(101MHz,DMSO)δ167.33,157.59,157.29,149.71,143.05,137.75,137.48,137.24,137.22,136.41,133.05,133.03,131.11,130.48,129.22,128.96,128.94,128.49,126.50,122.50,122.26 , 121.13, 120.53, 116.80, 109.68, 106.37, 101.17, 44.85, 20.84, 17.15, 12.13. HRMS (ESI) m / z: 487.2121 [M+H] + .
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