Category: 337915-79-4

Synthetic Route of 337915-79-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 337915-79-4 name is 5-Bromo-N1-methylbenzene-1,2-diamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The 5 – bromo – N1- Methyl phenyl – 1, 2 – diamine (1.02 g, 5 . 07 mmol) and 2 – (4 – (trifluoromethyl) phenyl) acetic acid (2.01 mg, 9 . 85 mmol) is added to the toluene (25 ml) in, 120 C oil bath is heated under reflux reaction 42 h. The reaction cooling to room temperature, concentrated under reduced pressure, the residue added to in DCM (60 ml), HCl aqueous solution for sequentially (1.0 M, 20 ml), saturated NaHCO3Aqueous solution (20 ml) and saturated NaCl aqueous solution (20 ml) washing, anhydrous Na2SO4Drying, concentrated under reduced pressure, the crude product by silica gel column chromatography (eluent: PE/EtOAc (v/v)=2/1), to obtain the product as a yellow solid (500 mg, 27%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-N1-methylbenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Zhong Xue; Wang Feng; Li Xuke; He Wei; Guan Mingyu; Liu Bing; Zhang Yingjun; Zheng Changchun; (105 pag.)CN108689942; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 337915-79-4,Some common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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: HATU (4.89 g, 12.9 mmol) was added to a solution of the intermediate 4-bromo-N2-ethylbenzene-1,2-diamine, DIPEA (6.40 mL, 36.7 mmol), and cyclopropanecarboxylic acid (0.98 mL, 12.2 mmol) in DMF (40 mL), and the mixture was stirred at rt for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in AcOH (40 mL) and the mixture was stirred at 80 C for 1 h. After concentration of the mixture, the residue was neutralized with satd NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane/EtOAc = 100/0 to 0/100) to give the title compound (1.2 g, 37%) as a pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-N1-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Article; Igawa, Hideyuki; Takahashi, Masashi; Shirasaki, Mikio; Kakegawa, Keiko; Kina, Asato; Ikoma, Minoru; Aida, Jumpei; Yasuma, Tsuneo; Okuda, Shoki; Kawata, Yayoi; Noguchi, Toshihiro; Yamamoto, Syunsuke; Fujioka, Yasushi; Kundu, Mrinalkanti; Khamrai, Uttam; Nakayama, Masaharu; Nagisa, Yasutaka; Kasai, Shizuo; Maekawa, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2486 – 2503;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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. Safety of 5-Bromo-N1-methylbenzene-1,2-diamine

[000814j To a stirred solution of compound 1 (0.1 g, 1 eq) in DMF (5 mL),TEA ( 0.101 g, 2 eq) and 4-chlorobutanoyl chloride (0.06 1 g, 1 eq) was added at 0 C and stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated under reduced pressure and the residue was basified using saturated sodium bicarbonate solution and extracted with ethyl acetate (2 X 20 mL). Combined organic extracts were washed with brine and dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was dissolved in acetic acid (5 mL) and was heated to 70 C for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated under vacuum and residue was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2 X 25 mL). Combined organic extracts were washed with brine and dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 80% EtOAc-hexane to afford the title compound 2. LCMS (mlz): 289.00 (M + 1).

The synthetic route of 5-Bromo-N1-methylbenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

[000821j To a stirred solution of compound 1 (2 g, 1 eq) in THF (40 mL), CDI (2.42 g, 1.5 eq) was added and heated to reflux for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate (100 mL) and washed with water. Organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the crude compound 2. LCMS (mlz): 226.90 (M + 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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. Recommanded Product: 5-Bromo-N1-methylbenzene-1,2-diamine

To a stirred solution of 5-bromo-N1-methylbenzene-1,2-diamine (38 g, 189 mmol) in THF (800 mL) was added CDI (37 g, 228 mmol) at room temperature under nitrogen atmosphere. The resulting mixture was refluxed for 16 h. The mixture was cooled to room temperature. The mixture was diluted with water (1 L) and stirred at room temperature for 30 min. The precipitated solids were collected by filtration and washed with water (200 mL). The filter cake was dried under vacuum to afford 6-bromo-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one (40 g, 93%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d 11.02 (br s, 1H), 7.35 (d, J = 1.9 Hz, 1H), 7.14 (dd, J = 8.2, 1.9 Hz, 1H), 6.92 (d, J = 8.2 Hz, 1H), 3.27 (s, 3H). LC/MS (ESI, m/z): [(M + 1)]+ = 227.10, 229.10

The synthetic route of 5-Bromo-N1-methylbenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, belongs to bromides-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 337915-79-4, COA of Formula: C7H9BrN2

Example 30 4- ( (4-Chlorobenzyl) oxy) -1- (2-isopropyl-l-methyl-lH- benzimidazol-6-yl) pyridin-2 (1H) -one A) 6-Bromo-2-isopropy1-1-methyl-lH-benzimidazole To a solution of 5-bromo-Nx-methylbenzene-l, 2-diamine. (122 mg) and isobutyric acid (0.056 ml) in DMF (2 ml) was added HATU (242 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. After being stirred, N, N-diisopropylethylamine (0.311 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04 and concentrated in vacuo. The resulting residue was stirred in AcOH (2.00 ml) at 90C for 1 h and at room temperature overnight. The mixture was quenched with saturated NaHCC>3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSC>4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (119 mg) as a pale yellow solid. MS (ESI+) : [M+H]+ 255.0.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

[000849j To a stirred solution of compound 3 (1 g, 1 eq) in POC13 (2 mL), cyclopropane carboxylic acid (0.5 mL) were added. The resulting reaction mixture was heated at 120 C for 3h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate (3 X 20 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 4. LCMS (mlz): 250.95 (M + 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-N1-methylbenzene-1,2-diamine

Step C: 7-Bromo-1-methylquinoxaline-2,3(1H,4H)-dione Under a protection of nitrogen, to 5-bromo-N-1-methylbenzene-1,2-diamine (7.7g, 38.3mmol) and triethylamine (9.69g, 95.75mmol) in 1,2-dichloroethane (80 mL) was added oxalyl chloride monoethyl ester (6.27g, 45.96mmol) at 0C. It was stirred at 25C for 2 hours. The temperature was raised to 60C for stirring for 3 hours. The reaction solution was filtered, and the filter cake was washed twice with water (20mL). The filter cake was dried to give the title compound. 1H NMR (400MHz, DMSO-d6) delta=12.07 (br. s., 1H), 7.51 (d, J=1.2 Hz, 1H), 7.33 (dd, J=1.6, 8.2 Hz, 1H), 7.07 (d, J=8.6 Hz, 1H), 3.47 (s, 3H).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; LIU, Shilan; LIANG, Guibai; WANG, Hongjian; ZHANG, Ming; CHEN, Shuhui; (93 pag.)EP3640247; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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. SDS of cas: 337915-79-4

[00320] To a solution of 5-bromo-Nl-methylbenzene-l,2-diamine (7.4 g, 37 mmol) in trimethyl orthoformate (100 mL) was added p-toluenesulfonic acid (0.36g, 1.9 mmol). The reaction mixture was heated at 100 C for 4 h, cooled, concentrated, dissolved in ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The crude product was used in next step without further purification. (7.3 g, yield 93%) MS (ESI+) e/z: 212.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 337915-79-4, its application will become more common.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; WO2014/100734; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-N1-methylbenzene-1,2-diamine

To a round bottom flask was added 4-bromo-N2-methylbenzene-1,2-diamine (1-2) (9.07 g, 45.1 mmol), sulfamide (8.84 g, 92 mmol), and finally anhydrous pyridine (75 mL). The reaction mixture was then heated to 125C while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 14 hours. The crude reaction mixture was then allowed to cool to room temperature, suspended in ethyl acetate and added 6N HCl until pH <3. Crude mixture was then filtered. Filtrate organics were separated, then washed with 6N HCl twice dried over sodium sulfate, filtered, and concentrated to give 6- bromo-1 -methyl- 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-3). HRMS (M+H)+:observed = 262.9486, calculated = 262.9484. The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; KELLY, Michael, J.; HARTINGH, Timothy, J.; WO2011/109277; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary