Application of 4152-90-3, A common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, molecular formula is C7H8ClN, 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.
3- [5,6-bis(methyloxy)-2-pyridinyll -N- [(3-chlorophenvDmethyll -2,4-dioxo-l ,2,3,4-tetrahvdro- 7-quinazolinecarboxamide; 24a) Methyl 2-amino-4-(3-chlorobenzylaminocarbonyl)benzoate; To a stirred suspension of 3-amino-4-(methoxycarbonyl)benzoic acid (1.0 g, 5.13 mmol, 1 eq.) in DMF (7 mL) was added HATU (2.1 g, 0.5.64 mmol, 1.1 eq.) and DIEA (0.98 mL, 0.11 mol, 1.1 eq.) and the mixture was stirred at rt for 5 minutes until all dissolved. The resulting solution was added to 3-chlorobenzylamine (0.69 mL, 5.64 mmol, 1.1 eq.) in DMF (3 mL) via syringe and stirred at rt for 30 minutes when LCMS showed that the reaction was complete. The solution was added dropwise to ice-water with stirring and the precipitate collected by vacuum filtration, washed with ice-water and dried under vacuum to yield the title product methyl 2-amino-4-(3 chlorobenzylaminocarbonyl)benzoate (24a) which was used without further purification. (Yield: 1.52g, 93percent); MS(ES+) m/e 319 (MH+); 1H NMR (400 MHz, OMSO-d6) delta ppm: 3.81 (s, 3 H) 4.44 (d, J 6.06 Hz, 2 H) 6.81 (s, 2 H) 6.97 (d, J 8.59 Hz, 1 H) 7.24 – 7.40 (m, 5 H) 7.77 (d, J 8.59 Hz, 1 H) 9.07 (t, J 6.06 Hz, 1 H)
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; GLAXOSMITHKLINE LLC; SCHULZ, Mark, James; WANG, Yonghui; WO2010/59549; (2010); A1;,
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