Electric Literature of 1196152-34-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.
(S)-2-Hydroxy-2,4-dimethylpentanoic acid (3073 g; 21 mol; 1.00 eq.), 4-dimethylaminopyridine (128 g; 1 mol; 0.05 eq.) and dichloromethane (24.5 L) are placed in a 100 L reactor. The reaction mixture is cooled to about 0 C. Pyridine (3.75 L) and dichloromethane (6 L) are added while maintaining the temperature at 0-5 C. (0238) Trimethylchlorosilane (5.8 L; 46 mol; 2.20 eq.) is added while maintaining the temperature below 5 C. The reaction mixture is warmed to 20 C. and stirred for 4 hours 30 minutes at this temperature, and then cooled to 0 C. N,N-Dimethylformamide (55 ml; 0.71 mol; 0.03 eq.) is added while maintaining the temperature below 5 C., and oxalyl chloride (1622 ml; 18.9 mol; 0.90 eq.) is then added while maintaining the temperature below 5 C. The reaction mixture is stirred for 1 hour at this temperature and N,N-dimethylformamide (27.50 ml; 0.36 mol; 0.02 eq.) is then added. The reaction mixture is warmed to about 20 C. and stirred for 1 hour at this temperature. (0239) A solution of 2-bromo-4-amino-6-methoxypyridine (3543 g; 17.4 mol; 0.83 eq.) in a dichloromethane (27.3 L)/pyridine (1.9 L) mixture is added to the preceding solution while maintaining the temperature below 25 C. The reaction mixture is stirred for 30 minutes at this temperature. The reaction progress is monitored by TLC with 5% control. (0240) A solution of acetic acid (23 L; 41 mol; 1.95 eq.) in ethanol (19 L) is prepared in a new disposable container of suitable volume and then poured into the reaction mixture while maintaining the temperature below 25 C. The reaction medium is stirred overnight at about 20 C. The reaction progress is monitored by TLC. (0241) An aqueous solution of hydrochloric acid (2.4 L; 12.00 M; 28.77 mol; 0.78 V) in water (27 L) is prepared in a new disposable container of suitable volume and then poured into the reaction medium and stirred for 10 minutes. The aqueous phase is discarded and the organic phase is then washed with water (30 L). The aqueous phase is discarded and the organic phase is then washed again with a solution prepared from NaOH (1 177.29 g; 29.43 mol; 1.40 eq.) in water (30 L). The aqueous phase is discarded and the organic phase is then washed again with water (30 L). (0242) The aqueous phase is discarded. The organic phase is clarified on a filter packed with active charcoal (921 g) and the cake is then washed with dichloromethane (10 L). The filtrate is then placed in the reactor and concentrated at reflux, distillate (37 L). Cyclohexane (43 L) is added to the reactor, which is then refluxed until the head temperature reaches 75 C. (distilled volume 22.5 L). Cyclohexane (10 L) is added and the reactor is allowed to cool to 27 C. An (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide initiator (138 g; 0.42 mol; 0.02 eq.) is added to promote the crystallization. The reaction mixture is cooled to 20 C. and then filtered through a 25 mum filter gauze. (0243) The reactor and the filter are rinsed with cyclohexane (10 L). The solid is dried in an oven at 45 C. under vacuum to give (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide (3.7 kg; 65%). (0244) 1H NMR (400 MHz, DMSO-d6): 10.0 (bs, 1H); 7.73 (s, 1H); 7.33 (s, 1H); 5.70 (bs, 1H); 3.80 (s, 3H); 1.79-1.67 (m, 2H); 1.49 (dd, J=13.6 & 5.2 Hz, 1H); 1.32 (s, 3H); 0.89 (d, J=6.4 Hz, 3H); 0.78 (d, J=6.4 Hz, 3H)
According to the analysis of related databases, 1196152-34-7, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Galderma Research & Development; BOITEAU, Jean-Guy; DAVER, Sebastien; RODEVILLE, Nicolas; (19 pag.)US2019/10124; (2019); A1;,
Pyridine – Wikipedia,
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