Electric Literature of 2854-16-2 ,Some common heterocyclic compound, 2854-16-2, molecular formula is C4H11NO, 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 444-(cyclopropylmethoxy)-N-(2-{[(2-hydroxy-2-methylpropyl)amino]methyl}-4-methyl-1H-indol-5-yl)benzamide4-(Cyclopropylmethoxy)-N-(2-formyl-4-methyl-1H-indol-5-yl)benzamide (298 mg) obtained in Reference Example 41 and 1-amino-2-methylpropan-2-ol (153 mg) were suspended in NMP (3.0 mL), acetic acid (1.0 mL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hr.Sodium triacetoxyborohydride (363 mg) was added, the mixture was stirred at room temperature for 16 hr, and diluted with ethyl acetate, and 2N aqueous sodium hydroxide solution (20 mL) was added at room temperature.The mixture was poured into water, and the organic layer was washed with water and then with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure.The residue was suspended in ethyl acetate, and the precipitate was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (307 mg, yield 85percent) as a brown solid.1H NMR (300 MHz, CDCl3) delta: 0. 34 – 0.43 (2 H, m), 0.63-0.72 (2 H, m), 1.22 (6 H, s), 1.25 – 1.36 (1 H, m), 2.45 (3 H, s), 2.61 (2 H, s), 3.88 (2 H, d, J=7.2 Hz), 4.02 (2 H, s), 6.38 (1 H, d, J=1.1 Hz), 6.98 (2 H, d, J=8.3 Hz), 7.19 (1 H, d, J=8.3 Hz), 7.34 (1 H, d, J=7.6 Hz), 7.58 (1 H, br. s.), 7.88 (2 H, d, J=8.0 Hz), 8.48 (1 H, br. s.).melting point: 186¡ãCelemental analysis (C25H31N3O3*0.2H2O)Calculated: C, 70.63; H, 7.44; N, 9.88.Found: C, 70.57; H, 7.38; N, 9.68.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2854-16-2, its application will become more common.
Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2522657; (2012); A1;,
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