Application of 89282-70-2,Some common heterocyclic compound, 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, molecular formula is C5H13NO, 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 N-(3-{[(2-methoxy-2-methylpropyl)amino]methyl}-8-methylquinolin-7-yl)-4-(tetrahydrofuran-2-ylmethoxy)benzamide monohydrochloride [Show Image] N-(3-Formyl-8-methylquinolin-7-yl)-4-(tetrahydrofuran-2-ylmethoxy)benzamide (1.0 g) obtained in Reference Example 2 and 2-methoxy-2-methylpropan-1-amine 0.5 oxalate (600 mg) were suspended in 1-methyl-2-pyrrolidone (10 mL) and acetic acid (5.0 mL) and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (2.35 g) was added and the mixture was stirred at room temperature for 3 hr. 1N Aqueous sodium hydroxide solution was added to quench the reaction and basify the mixture. The mixture was partitioned and extracted with ethyl acetate, the organic layer was added to a solution of citric acid (4.0 g) in water (40 mL)-dimethyl sulfoxide (20 mL), and the mixture was washed with ethyl acetate. 1N Aqueous sodium hydroxide solution was added to the aqueous layer, and the mixture was partitioned and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained amorphous product was dissolved in ethyl acetate, and 4N hydrogen chloride-ethyl acetate solution (0.15 mL) was added. The obtained solid was recrystallized from ethyl acetate-methanol to give the title compound (101 mg, yield 8%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) delta: 1.20 (6 H, s), 1.68 – 1.72 (1 H, m), 1.87 – 1.90 (2 H, m), 1.96 – 2.00 (2 H, m), 2.68 (3 H, s), 2.97 – 3.00 (1 H, m), 3.11 (3 H, s), 3.68 – 3.81 (2 H, m), 4.02 – 4.06 (2 H, m), 4.16 – 4.20 (1 H, m), 4.42 (2 H, s), 7.09 (2 H, d, J=8.7 Hz), 7.75 (1 H, d, J=8.7 Hz), 7.90 (1 H, d, J=8.7 Hz), 8.04 (2 H, d, J=8.7 Hz), 8.72 (1 H, s), 9.20 (1 H, s), 9.27 (2 H, br), 10.25 (1 H, s).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-2-methylpropan-1-amine, its application will become more common.
Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2392573; (2011); A1;,
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