Application of 16452-01-0, These common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, 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 705,5-dimethyl-3-[6-(7-methylspiro[2H-benzofuran-3 ‘-cyclopropanel-4-yl)oxy-3-pyridyllimidazoli2.4- dione To a solution of triphosgene (30 mg, O.lmmol) in dry DCM (1ml) at OPC, under nitrogen atmosphere, DIPEA (0.175 ml, 1.0 mmol) was added followed by the addition (slowly added) of a solution of 6-(7- methylspiro[2H-benzofuran-3,l’-cyclopropane]-4-yl)oxypyridin-3-amine (Intermediate 158, 27 mg, 0.1 mmol) in dry DCM (2ml) and the reaction mixture was stirred for 15 minutes at the same temperature. After that a solution of Methyl 2-amino-2-methylpropanoate hydrochloride (30mg, 0.2mmol) in dry DCM (2ml) was added and the reaction mixture was stirred for 30 minutes at OPC. The reaction was quenched with a 1M aqueous solution of HCI (5ml), diluted with DCM (10ml) and two phases were separated. The organic layer was washed with brine (10ml), dried (IS^SC^), filtered and evaporated affording the urea intermediate as yellow foam.The urea was dissolved in MeOH (5ml), NaOMe (lOmg, 0.19 mmol) was added and the reaction mixture was stirred for 15 minutes at room temperature. The reaction was quenched with an aqueous saturated solution of ammonium chloride (20ml) and diluted with ethyl acetate (40ml). Two phases were separated and the organic layer was dried (Na2S04), filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a lOg SNAP column and cyclohexane/ethyl acetate 75:25 to cyclohexane/ethyl acetate 25:75 as eluents affording the title compound (23mg) as a white solid.1H-NMR (400 MHz, DMSO-d6) delta ppm: 8.62 (1H, s), 8.14 (1H, d), 7.86 (1H, dd), 7.05 (1H, d), 6.92 (1H, d), 6.43 (1H, d), 4.44 (2H, s), 2.14 (3H, s), 1.40 (6H, s), 1.08-1.13 (2H, m), 0.96 (3H, t), 0.85-0.90 (2H, m). LC/MS: QC_3_MIN: Rt = 2.016 min; 380 [M+H]+.
Statistics shows that 3-Methoxy-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 16452-01-0.
Reference:
Patent; AUTIFONY THERAPEUTICS LIMITED; ALVARO, Giuseppe; DAMBRUOSO, Paolo; MARASCO, Agostino; TOMMASI, Simona; DECOR, Anne; LARGE, Charles; WO2012/76877; (2012); A1;,
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