Synthetic Route of 7169-95-1 ,Some common heterocyclic compound, 7169-95-1, molecular formula is C7H6BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
EXAMPLE 5(S)-6-(2-hydroxy-2-methylpropyl)-6-isopropyl-3-((S)-l-(4-(2-methyl-[l,2,4]triazolo[l,5-a]pyridin-6-yl)phenyl)ethyl)-l,3-oxazinan-2-oneTo a solution of 6-bromo-2-methyl-[l,2,4]triazolo[l,5-a]pyridine (9.5 mg, 0.045 mmol) in DME (3 mL) was added Pd(PPh3)4 (5.2 mg, 0.0045 mmol) under N2. After being stirred at room temperature for 1 hour, the mixture was added a solution of (2^-6- (2-hydroxy-2-methylpropyl)-6-isopropyl-3-(f5>;l-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)ethyl)-l,3-oxazinan-2-one (20 mg, 0.045 mmol) in ethanol (1.5 mL) and saturated NaHCO3 solution(l mL). The mixture was heated to reflux for 2 hours under N2. The reaction mixture was treated with ethyl acetate (10 mL) and water (10 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by preparative HPLC to give f5^-6-(2-hydroxy- 2-methylpropyl)-6-isopropyl-3-(5y)- 1 -(4-(2-methyl-[ 1 ,2,4]triazolo[ 1 ,5-a]pyridin-6-yl) phenyl)ethyl)-l,3-oxazinan-2-one (6.00 mg, 30%). LC-MS Method 2 tR = 0.99 min, m/z = 451. 1H NMR (CD3OD): 0.90 (d, 3H), 1.00 (d, 3H), 1.33 (d, 6H), 1.65 (d, 3H), 1.78 (d, IH), 1.93 (m, 2H), 2.17 (m, IH), 2.28 (m, IH), 2.58 (s, 3H), 2.84 (m, IH), 3.39 (m, IH), 5.73 (q, IH), 7.52 (d, 2H), 7.76 (m, 3H), 8.01 (d, IH), 8.99 (s, IH). (S)-6-(2-hydroxy-2-methylpropyl)-6-isopropyl-3-((S)-l-(4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenyl)ethyl)-l,3-oxazinan-2-one was prepared as described in WO 2009/134400 Example 17.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7169-95-1, its application will become more common.
Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; WO2010/91067; (2010); A2;,
Pyridine – Wikipedia,
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