[1,2,3] triazolyl substituted quinolines and coumarins as inhibitors of leukotriene biosynthesis
A compound, selected technology, applied in the direction of drug combination, medical preparation containing active ingredient, anti-inflammatory agent, etc.
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Embodiment 1
[0172] (S)-4-(3-fluorophenyl)-7-({4-[1-hydroxyl-1-(trifluoromethyl)propyl]-1H-1,2,3-triazole-1- Base} A Base) -2H-benzopyran-2-one
[0173]
[0174] Step 1: 3-(Trifluoromethyl)-1-(trimethylsilyl)pent-1-yn-3-ol
[0175]
[0176] To a solution of trimethylsilylacetylene (6.0 g, 61.1 mmol) in THF (80 mL) cooled at -78 °C was added dropwise 1.6 M n-butyllithium in hexane (38 mL, 61.1 mmol). The solution was then stirred for 1 hour before a solution of trifluoromethyl ethyl ketone (10 g, 79.4 mmol) in THF (25 ml) was added slowly. The reaction was stirred at -78°C for 4 hours. The reaction was then poured into saturated ammonium chloride solution and the aqueous layer was extracted (4x) with diethyl ether. The combined organic layers were washed with brine, washed with MgSO 4 Dry, filter and concentrate under reduced pressure. The obtained crude residue was used directly in the next step. 1 H NMR (400MHz, acetone-d 6 ): 5.83 (s, 1H), 1.80 (q, 2H), 1.14 (t, 3H), 0....
Embodiment 1A
[0203] Preparation of (S)-4-(3-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazole-1 -base} A Alternatives to -2H-benzopyran-2-one
[0204] step 1 A 100 mL flask equipped with a mechanical stirrer, thermocouple, nitrogen inlet and cooling bath was charged with trimethylsilylacetylene (3.5 g, 1.50 eq) and MTBE (12.0 mL). The mixture was cooled to -67°C and 2.26M n-BuLi (11.2 mL, 1.05 eq) was added to the solution over 1 h keeping the reaction mixture below -50°C. The reaction mixture was aged for 45 minutes, then 1,1,1-trifluoro-2-butanone (3.3 mL, 1.00 eq) was added over a period of 1 hour (internal temperature maintained below -50°C). The mixture was aged for 20 minutes, then p-nitrobenzoyl chloride (4.7 g, 1.05 eq) in THF (7.0 mL) was added over 1 hour, keeping the reaction mixture below -30 °C. The reaction mixture was allowed to warm to 5°C over 3 hours.
[0205] The reaction was quenched by carefully adding water (9.0 mL). Solka Floc (0.2...
Embodiment 2
[0224] (S)-4-(4-fluorophenyl)-7-[4-(1-hydroxy-1-trifluoromethyl-propyl)-[1,2,3]triazol-1-ylmethyl ]-Benzo Pyran-2-one
[0225]
[0226] 1 H NMR (400MHz, acetone-d 6 ): 8.21(s, 1H), 7.7-7.6(m, 1H), 7.53(d, 1H), 7.42-7.35(m, 3H), 7.31(d, 1H), 6.4(s, 1H), 5.85( s, 2H), 5.47 (s, 1H), 2.41-2.3 (m, 1H), 2.15-2.05 (m, 1H), 0.86 (t, 3H).
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