Category: 89979-12-4

Adding a certain compound to certain chemical reactions, such as: 89979-12-4, name is 5-Chloro-2-(methylsulfonamido)benzoic acid, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 89979-12-4, Formula: C8H8ClNO4S

Mixed 5-chloro-2-(methylsulfonamido)benzoic acid (47mg, 0.187mmol) with HATU (71mg, 0.187mmol) and dissolved in anhydrous DMF (lmL). Stirred for lhr. Dissolved amine hydrogen chloride (49mg, 0.17mmol) in anhydrous DMF (lmL) and added to the reaction. Added TEA (71uL, 0.5 lmmol). Stirred for 16 hrs. Diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution twice. Dried organic extract over anhydrous sodium sulfate and then concentrated under reduced pressure. Purified with silica gel column (0-50% EtOAc in hexanes) to give intermediate 55 (57mg, 39% yield). LC/MS (m/z): 482.2 [M+H]+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Chloro-2-(methylsulfonamido)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 89979-12-4, These common heterocyclic compound, 89979-12-4, name is 5-Chloro-2-(methylsulfonamido)benzoic acid, 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.

General procedure: To a solution of 5-chloro-N,6-dimethyl-2-[(1S)-1-(methylamino)propyl] pyrazolo[1,5-a] pyrimidin-7-amine (97 mg,0.361 mmol) and 5-chloro-2-(methylsulfonamido) benzoic acid(99 mg, 0.397 mmol) in N,N-dimethylformamide (1.0 mL)was added trimethylamine (0.25 mL, 1.80 mmol) and1-[bis(dimethylamino) methylene]-1H-1,2,3-triazolo[4,5-b]-pyridinium 3-oxide hexafluorophosphate (0.17 g, 0.433 mmol).After stirring at room temperature for 1 h, the reaction mixturewas purified by reversed-phase preparative HPLC toobtain 5-chloro-N-{(1S)-1-[5-chloro-6-methyl-7-(methylamino)-pyrazolo[1,5-a] pyrimidin-2-yl] propyl}-2-[(methanesulfonyl)-amino]-N-methylbenzamide (0.13 g, 0.904 mmol, 90%) as acolorless powder

The synthetic route of 89979-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamaguchi-Sasaki, Toru; Tamura, Yunoshin; Ogata, Yuya; Kawaguchi, Takanori; Kurosaka, Jun; Sugaya, Yutaka; Iwakiri, Kanako; Busujima, Tsuyoshi; Takahashi, Ryo; Ueda-Yonemoto, Naoko; Tanigawa, Eiji; Abe-Kumasaka, Tomoko; Sugiyama, Hiroyuki; Kanuma, Kosuke; Chemical and Pharmaceutical Bulletin; vol. 68; 4; (2020); p. 345 – 362;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 89979-12-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 89979-12-4, name is 5-Chloro-2-(methylsulfonamido)benzoic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 63Starting material intermediate 60 (200 mg) was dissolved in 10 ml of dioxane, to the solution was added concentrated HC1 (1 ml). The reaction was completed in 30mins, solvent was evaporated and the residue was used in the next step. 2- methanesulfonamido-5-chlorobenzoic acid (20 mg, 0.08 mmol), HATU (38 mg, 0.1 mmol) were dissolved in anhydrous DMF (2 ml). After activation for 1 hour, to the above solution was added previous step crude product (20 mg, 0.05 mmol) and triethylamine (40 mu). The reaction was stirred under nitrogen for lh. Solvents were removed by rotary evaporation. The residue was purified with preparatory HPLC to provide compound 63. (Yield 9 mg, 26 %).1H-NMR (CD3OD, 400 MHz): delta 8.78 (s, 1H), 7.65 (d, J= 7.2 Hz, 1H), 7.25 (d, J= 7.2 Hz, 1H), 7.18 (s, 1H), 6.68 (s, 1H), 6.1 1 (s, 1H), 4.46 (s, 2H), 3.83 (s, 5H), 3.81 (s, 3H), 3.04-2.94 (m, 3H), 2.91-2.80 (m, 3H), 2.57-2.48 (m, 3H), 2.22-2.16 (m, 2H), 1.76-1.74 (m, 2H), 1.51 (s, 2H). LCMS m/z [M+H]+ C26H31C1N604S requires: 559.18. Found 559.24HPLC Tr (min), purity %: 2.74, 98%

The synthetic route of 5-Chloro-2-(methylsulfonamido)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 89979-12-4, name is 5-Chloro-2-(methylsulfonamido)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Chloro-2-(methylsulfonamido)benzoic acid

Mixed 5-chloro-2-(methylsulfonamido)benzoic acid (28mg, 0.109mmol) with HATU (42mg, 0.109mmol) and dissolved in anhydrous DMF (300uL). Stirred for Ihr. Dissolved hydrogenation product in anhydrous DMF (300uL) and added to the reaction. Added TEA (30uL, 0.218mmol).Stirred for 12 hrs. Diluted with acetonitrile and purified with Prep HPLC to give compound 40 (22mg, 32% yield).1H NMR (400MHz, CD3OD): delta 7.49 (m, 3H), 6.26 (m, 1H), 6.08 (m, 1H), 4.78 (m, 1H), 4.57 (m, 2H), 4.14 (m, 2H), 3.47-3.34 (m, 2H), 3.01 (m, 4H), 2.76 (s, 3H), 2.40-2.05 (m, 2H), 1.73- 1.50 (m, 4H). LC/MS (m/z): 519.2 [M+H]+

According to the analysis of related databases, 89979-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

89979-12-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 89979-12-4 as follows.

Example 12 Preparation of Intermediate 11 [0467] [0468] HATU (1.37 g, 3.59 mmol) was added to a solution of 5-chloro-2-(methylsulfonamido)benzoic acid (823 mg, 3.29 mmol) in DMF (15.0 mL), and the reaction mixture was stirred at room temperature. After 1 h, a solution of crude intermediate 6 (220 mg, 2.99 mmol) in DMF (1 mL) was added followed by the addition of triethylamine (2.00 mL, 14.3 mmol), and the reaction mixture was stirred at room temperature for 19 h. The reaction mixture was partitioned between ethyl acetate (250 mL) and saturated aqueous sodium bicarbonate solution (200 mL), and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution (200 mL) and saturated sodium chloride solution (200 mL), was dried over Na2SO4, and was concentrated under reduced pressure. The crude residue was purified via SiO2 column chromatography (12 g SiO2 Combiflash HP Gold Column, 0-100% ethyl acetate/hexanes) to afford intermediate 11 (736.2 mg, 51% (2-steps)) as a white solid. [0469] 1H NMR (CDCl3, 400 MHz): delta 10.05 (br s, 0.2H), 9.13 (br s, 1H), 8.95 (br s, 1H), 8.81 (br s, 0.2H), 7.70 (d, J=8.8 Hz, 1H), 7.56 (d, J=8.8 Hz, 0.2H), 7.40 (dd, J=8.8, 2.4 Hz, 1H), 7.33 (d, J=2.4 Hz, 1H), 7.31 (d, J=4.4 Hz, 0.2H), 6.45 (s, 1H), 6.40 (br s, 0.2H), 6.28 (br d, J=4.4 Hz, 1H), 5.01 (br s, 0.2H), 4.54 (br d, J=14.0 Hz, 0.2H), 3.35 (br d, J=13.2 Hz, 1H), 3.15-3.03 (m, 1H), 2.92 (s, 3H), 2.39 (s, 3H), 2.13-1.98 (m, 1H), 1.90-1.59 (m, 2H), 1.59-1.31 (m, 3H). [0470] 13C NMR (CDCl3, 100 MHz): delta 167.09, 156.12, 153.13, 147.86, 135.68, 131.79, 131.66, 131.38, 130.12, 125.91, 125.44, 117.08, 93.74, 47.65, 44.07, 39.81, 27.83, 25.47, 19.78, 16.90. [0471] LCMS (ESI) m/z 482.1 [M+H]+, tR=2.79 min. [0472] HPLC tR (min), purity %: 5.438, 99% [0473] Rf=0.47 (50% EtOAc/hexanes). [0474] Chiral HPLC, 99% ee (Chiralpak IC 5 mM, 4.6¡Á150 mm, 10-95% MeCN/H2O, 0.05% trifluoroacetic acid modifier) (S)-isomer tR=29.739 min, (R)-isomer tR=29.495 min.

According to the analysis of related databases, 5-Chloro-2-(methylsulfonamido)benzoic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Siegel, Dustin; Sperandio, David; Yang, Hai; Sangi, Michael; Parrish, Jay P.; Hui, Hon Chung; US2013/273037; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics