Category: 6980-08-1

Synthetic Route of 6980-08-1 , The common heterocyclic compound, 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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.

a) Diethyl 2-(2-amino-3-nitropyridin-4-yl)malonate (A 132) NaH (60% dispersion in mineral oil, 0.830 g, 20.7 mmol) was added to a solution of diethyl malonate (3.16 ml_, 20.7 mmol) in NMP (50 ml_) and the resulting solution was stirred at room temperature for 10 minutes. 4-Chloro-3-nitropyridin-2-amine A14 (1.00 g, 5.76 mmol) was then added and the mixture heated at 50 C for 2 hours. The mixture was cooled to room temperature and diluted with EtOAc (250 ml_) and water (100 ml_). The organic layer was separated and washed with water (100 ml_) followed by brine (100 ml_). This process was repeated three times before the organic layer was dried (Na2S04), filtered and the filtrate concentrated under reduced pressure to give a yellow oil which was purified by silica gel column chromatography (40 g Si02 cartridge, 0-100% EtOAc in petroleum benzine 40-60 C) to give the title compound as a yellow solid (1.69 g, 99%). H NMR (400 MHz, ck-DMSO) delta 8.28 (d, J = 4.9 Hz, 1 H), 7.53 (s, 2H), 6.58 (d, J = 5.0 Hz, 1 H), 5.20 (s, 1 H), 4.18 (qd, J = 7.1 , 0.9 Hz, 4H), 1.18 (t, J = 7.1 Hz, 6H). LCMS-B: rt 3.20 min, m/z (positive ion) 298 [M+H]+.

The synthetic route of 6980-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; STUPPLE, Paul Anthony; WALKER, Scott Raymond; PINSON, Jo-Anne; LAGIAKOS, Helen Rachel; LUNNISS, Gillian Elizabeth; HOLMES, Ian Peter; STUPPLE, Alexandra Elizabeth; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; KERSTEN, Wilhelmus Johannes Antonius; CAMERINO, Michelle Ang; WO2014/128465; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6980-08-1, Adding some certain compound to certain chemical reactions, such as: 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine,molecular formula is C5H4ClN3O2, 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 6980-08-1.

4-Chloro-3-nitropyridin-2-amine (0.1 0 g, 0.58 mmol) was dissolved in dryacetonitrile (20 ml). To the stirred solution was then added N-bromosuccinimide (0.124g, 0.70 mmol), and the reaction mixture was heated at 80 C for 1 h. Volatiles wereremoved in vacuo and the residue purified by silica column chromatography (elution with25 dichloromethane) to provide the title compound as a pale brown powder (0.125 g, 85%).1 H-NMR (500 MHz, DMSO-d6) 7.35 (s, 2H, NH2), 8.41 (s, 1 H, 6-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. 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190320; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6980-08-1, Adding some certain compound to certain chemical reactions, such as: 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine,molecular formula is C5H4ClN3O2, 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 6980-08-1.

To 400 mg (2.32 mmol) of 5-N-BOC-amino-8-hydroxy-quinoline dissolved in 30 mL DMF (dry), were added under stirring and argon atmosphere, 360 mg (3.20 mmol) tert-BuOK. After 30 minutes, 400 mg (2.32 mmol) 2-amino-3-nitro-4-chloropyridine were added at once and the reaction mixture heated at 850C (bath) for 5 hours. After cooling, 200 mL AcOEt were added and the solution extracted with 2 x 200 mL brine. The solution was dried (MgSO4) and evaporated under vacuum. The residue was purified on an lsolute column (Flash Si II; 50 g, 170 mL) eluted with AcOEt. The title compound was obtained as a yellow solid: 0.534 g. Yield: 58%. 1H NMR (500 MHz, DMSO-d6) delta: 1.51 (s, 9H, C(CH3J3), 5.65 (d, 1 H, HPyr, J=5.6 Hz), 7.14 (S, 2H1 NH2), 7.58-7.61 (m, 1 H1 HArom), 7.64 (d, 1 H, HArom, J= 8.3 Hz), 7.74 (d, 1 H, HArom, J= 8.3 Hz), 7.82 (d, 1 H, HPyr), 8.53-8.55 (m, 1H, Harom), 8.84-8.86 (m, 1H, Harom), 9.51 (S, 1 H, NH); LC-MS, tR = 6.51 min, m/z: 397.1 (M)+, calcd for C19H19N5O5.

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. 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL (THE); WO2009/130487; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6980-08-1 , The common heterocyclic compound, 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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.

Step 1 To a solution of 4-chloro-3-nitropyridin-2-amine (LXXXI) (5.00 g, 28.9 mmol, 1.00 eq) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (LXXXII) (7.1 g, 34.6 mmol, 1.20 eq) in a mixture of toluene (30 mL), H2O (18 mL) and EtOH (6 mL) was added Pd(PPh3)4(1.0 g, 0.87 mmol, 0.03 eq) and Na2CO3 (6.1 g, 57.6 mmol, 2 eq). The mixture was stirred at 75 C. for 15 h under a nitrogen atmosphere. The reaction mixture was then poured into brine (100 mL) and extracted with EtOAc (30 mL*3), the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified by chromatography on silica gel (PE:EtOAc=5:1-1:1) to afford 3-nitro-[4,4′-bipyridin]-2-amine (LXXXIII) (1.80 g, 8.33 mmol, 28.8% yield) as a yellow solid. ESIMS found C10H8N4O2 m/z 217.1 (M+H).

The synthetic route of 6980-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6980-08-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, molecular weight is 173.5572, as common compound, the synthetic route is as follows.

General procedure: To a solution of the pyridine 3 (300 mg, 1.73 mmol) [51] in absolute ethanol (10 mL) were added triethylamine (0.5 mL, 3.58 mmol) and the aniline 6 (500 mg, 1.99 mmol) [45] and the mixture was heated at reflux for 8 h. The solvent was vacuum evaporated, water was added to the residue and the precipitate was filtered, washed with water, dried and purified using silica gel column chromatography (dichloromethane) to give pure 7 (440 mg, 65%).

Statistics shows that 6980-08-1 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-nitropyridin-2-amine.

Reference:
Article; Gavriil, Efthymios-Spyridon; Doukatas, Aris; Karampelas, Theodoros; Myrianthopoulos, Vassilios; Dimitrakis, Spyridon; Mikros, Emmanuel; Marakos, Panagiotis; Tamvakopoulos, Constantin; Pouli, Nicole; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 393 – 409;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6980-08-1, Adding some certain compound to certain chemical reactions, such as: 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine,molecular formula is C5H4ClN3O2, 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 6980-08-1.

4-Chloro-3-nitropyridin-2-amine (500 mg, 2.89 mmol) and 4-amino-2-fluorophenol (403.8 mg, 3.18 mmol) were mixed in dry DMF (10 mL), and t-BuOK (356.1 mg, 3.18 mmol) was added. This mixture was heated to 80 C under N2 for 1 h, then cooled to room temperature. Water (50 mL) was added to quench the reaction, and the mixture was extracted with EA (3 × 50 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4, concentrated in vacuum, and purified by column chromatography to yield the corresponding ether 20b (618.0 mg, 81%). 1H NMR (300 MHz, DMSO) delta 7.95 (dd, J = 5.8, 0.7 Hz, 1H), 6.96 (t, J = 8.7 Hz, 1H), 6.54 – 6.40 (m, 2H), 6.15 (s, 2H), 6.03 (dd, J = 5.7, 1.3 Hz, 1H), 3.80 (s, 2H). EI-MS m/z: 264 (M)+.

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. 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; An, Xiao-De; Liu, Hongyan; Xu, Zhong-Liang; Jin, Yi; Peng, Xia; Yao, Ying-Ming; Geng, Meiyu; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry Letters; vol. 25; 3; (2015); p. 708 – 716;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, 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, Computed Properties of C5H4ClN3O2, blongs to pyridine-derivatives compound. Computed Properties of C5H4ClN3O2

Dry DMSO (20 mL) was added to NaH (1.029 g of a 60% dispersion in mineral oil, 25.7 mmol) in a round bottom flask under argon. After 5 minutes, solid fert-butyl 2-fluoro-4- hydroxyphenylcarbamate (5.59 g, 24.6 mmol) was added in three portions, giving a dark solution, which, after 15 minutes of stirring at room temperature, was treated with 4-chloro-3-nitropyridin-2-amine (4.23 g, 24.4 mmol) at once. The dark red solution was heated to 0C for 1 hour and allowed to cool down to room temperature. EtOAc (150 mL) and H20 (200 mL) were subsequently added to the solution and the organic layer was isolated. The aqueous layer was extracted with EtOAc (3 x 100 mL) and the combined organic layers were washed once with saturated NaHC03 (150 mL), dried (MgS04), filtered, and concentrated to dryness to give a bright yellow solid. This material was used in the next step without further purification.Yield: 8.68 g (98%). 1H-NMR (DMSO-d6), delta (ppm), J (Hz): 1.46 (s, 9H, C(CH3)3), 6.08 (d, 1 H, PyrH), 7.01 (m, 1 H, ArH), 7.18 (br s, 2H, NH2), 7.22 (m, 1 H, ArH), 7.67 (m, 1 H, ArH), 8.04 (d, 1 H, PyrH), 9.03 (s, 1 H, NHBoc); 19F-NMR (DMSO-d6), delta (ppm): -120.7; LC-MS (4.72 min): m/z calcd. for C,6H17FN405 [M+H+]: 365.0; found:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6980-08-1, 4-Chloro-3-nitropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL (THE); SPRINGER, Caroline; NICULESCU-DUVAZ, Ion; MARAIS, Richard; NICULESCU-DUVAZ, Dan; ZAMBON, Alfonso; MENARD, Delphine; WO2011/92469; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, 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, 6980-08-1, blongs to pyridine-derivatives compound. Product Details of 6980-08-1

Step 4 A solution of N-(3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)methanesulfonamide (CVII) (6.83 g, 20.75 mmol, 1.2 eq), 4-chloro-3-nitropyridin-2-amine (LXXXI) (3.0 g, 17.29 mmol, 1.0 eq), Na2CO3 (6.41 g, 60.52 mmol) and Pd(dppf)Cl2 (641.27 mg, 864.50 mumol) in dioxane (40 mL) and H2O (8 mL) was de-gassed and then heated to 80 C. overnight under N2. TLC (PE:EtOAc=1:1) showed the starting material was consumed completely. The reaction mixture was poured into H2O (300 mL). The mixture was extracted with EtOAc (3*250 mL). The organic phase was washed with saturated brine (300 mL), dried over anhydrous NaSO4, concentrated in vacuum to give a residue. The crude product was purified by silica gel chromatography (PE:EtOAc=10:1) to give N-(3-(2-amino-3-nitropyridin-4-yl)-5-fluorobenzyl) methanesulfonamide (CVIII) (2.2 g, 6.46 mmol, 37.4% yield) as brown solid. ESIMS found C13H13FN4O4S m/z 341.1 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6980-08-1, its application will become more common.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Chloro-3-nitropyridin-2-amine

2-Amino-3-nitro-4-chloropyridine (967 mg, 5.59 mmol) was dissolved in isopropanol (20 mL) and DIPEA (1.85 mL, 11.18 mmol) was added followed by N-methylpiperazine (0.744) mL, 6.71 mmol). The mixture was reacted at 90 C. for 12 h. A large amount of gold solid was isolated by cooling and was filtered, washed with isopropyl alcohol and ether in that order, and dried in vacuo to give the title compound (1.21 g, yield 92%) as a golden yellow solid.

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, 6980-08-1, 4-Chloro-3-nitropyridin-2-amine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Cao Bin; (103 pag.)CN103570683; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, 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, 6980-08-1, blongs to pyridine-derivatives compound. Application In Synthesis of 4-Chloro-3-nitropyridin-2-amine

Step 1 A solution of 2-chloro-3-nitro-pyridin-4-amine (LXXXI) (1.5 g, 8.64 mmol), 2-(5-fluorothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (XCIV) (2.96 g, 12.96 mmol), Pd(dppf)Cl2 (632 mg, 0.86 mmol) and Cs2CO3 (5.63 g, 17.29 mmol) in dioxane (30 mL) and H2O (5 mL) was de-gassed and then heated to 100 C. under N2 for 3 h. TLC (PE:EtOAc=1:1) showed the starting material was consumed completely. The mixture was concentrated in vacuum to give a residue, which was purified by column chromatography to afford 4-(5-fluorothiophen-2-yl)-3-nitropyridin-2-amine (XCV) (800 mg, 3.34 mmol, 38.7% yield). ESIMS found C9H6FN3O2S m/z 240.1 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6980-08-1, its application will become more common.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem