Category: 700811-29-6

Electric Literature of 700811-29-6 ,Some common heterocyclic compound, 700811-29-6, molecular formula is C5H6ClN3, 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 solution of 4-amino-2-chloropyridine (1.0 g, 7.78 mmol) in 20% sulfuric acid (20 mL) was cooled to 0 C and treated with a solution of sodium nitrite (564 mg, 8.17 mmol) in water (3 mL) at a rate such that the reaction temperature did not exceed 10 C. After 15 minutes, the solution was added to a 0C suspension of tin (li) chloride in 20% sulfuric acid (20 mL). The frothy suspension was stirred for 15 minutes at 0 C and then warmed to room temperature over 15 minutes. The mixture was poured into 100 mL of ice water and made basic with concentrated ammonium hydroxide. The product was extracted with diethyl ether and ethyl acetate repeatedly. The organic layers were dried (sodium sulfate) and concentrated to give crude 2-chloro-4-hydrazinopyridine as a yellow solid (830 mg, 5.78 mmol). The solid was dissolved in tetrahydrofuran (5 mL) and diluted with diethyl ether (15 mL). The solution was treated with 1 N HCI in diethyl ether (5.8 mL, 5.8 mmol). The white precipitate was filtered and washed with ether to give 2-chloro-4-hydrazinopyridine hydrochloride as a white solid (995 mg, 5.53 mmol, 71 % yield). LC-MS (ES+) MH+ = 144.’H NMR (300 MHz, DMSO-d6) b 10.0-9. 40 (br s, 4H), 8.07 (d, J = 6. 1, 1 H), 6.95 (d, J = 1.9, 1 H), 6.86 (dd, J = 5.8, 2.0, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,700811-29-6, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/58176; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 700811-29-6, 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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine, molecular formula is C5H6ClN3, The 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.

To a solution of 1.4 g of (2-Chloro-pyridin-4-yl) -hydrazine (9.79 MMOL, 1.51 equiv) in 30 mL of NMP was added sequentially 2.0 g of N-CYANO-N – (4-ETHOXYCARBONYLPHENYL)-O- phenylisourea (6.45 MMOL, 1.00 equiv) and 10 mL of Hunig’s base. The resulting solution was warmed to 220 C via microwave irradiation for 6 min. The reaction mixture was poured into 100 mL of water and the resulting solid was filtered, yielding 3.0 g of a wet solid, which was dissolved in 40 mL of THF. To the stirred reaction mixture was added 1.50 g of nitrosonium tetrafluoroborate (12.9 MMOL, 2.0 equiv). Rapid bubbling was observed and stirring was continued for 1 hr. 4- [L- (2-CHLORO-PYRIDIN-4-YL)-LH [1, 2,4] TRIAZOL-3-YLAMINO]-BENZOIC acid ethyl ester was filted out of the reaction mixture, yielding 2.0 g (5.83 MMOL, 90.4 % yield) as a yellow SOLID. H NMR (500 MHz, DMSO-d6) 8 10.20 (1 H, s), 9.40 (1 H, s), 8.52 (1 H, d), 8.02 (1 h, s), 7.91 (3 H, m), 7.74 (2 H, d), 7.15 (1 H, br s), 4.27 (2 H, q), 1.31 (3 H, t) ppm. LC/MS : 3.64 min/344.01 (M+1).

According to the analysis of related databases, 700811-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LEDEBOER, Mark W.; DAVIES, Robert J.; WO2005/13982; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 700811-29-6 ,Some common heterocyclic compound, 700811-29-6, molecular formula is C5H6ClN3, 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 solution of 4-amino-2-chloropyridine (1.0 g, 7.78 mmol) in 20% sulfuric acid (20 mL) was cooled to 0 C and treated with a solution of sodium nitrite (564 mg, 8.17 mmol) in water (3 mL) at a rate such that the reaction temperature did not exceed 10 C. After 15 minutes, the solution was added to a 0C suspension of tin (li) chloride in 20% sulfuric acid (20 mL). The frothy suspension was stirred for 15 minutes at 0 C and then warmed to room temperature over 15 minutes. The mixture was poured into 100 mL of ice water and made basic with concentrated ammonium hydroxide. The product was extracted with diethyl ether and ethyl acetate repeatedly. The organic layers were dried (sodium sulfate) and concentrated to give crude 2-chloro-4-hydrazinopyridine as a yellow solid (830 mg, 5.78 mmol). The solid was dissolved in tetrahydrofuran (5 mL) and diluted with diethyl ether (15 mL). The solution was treated with 1 N HCI in diethyl ether (5.8 mL, 5.8 mmol). The white precipitate was filtered and washed with ether to give 2-chloro-4-hydrazinopyridine hydrochloride as a white solid (995 mg, 5.53 mmol, 71 % yield). LC-MS (ES+) MH+ = 144.’H NMR (300 MHz, DMSO-d6) b 10.0-9. 40 (br s, 4H), 8.07 (d, J = 6. 1, 1 H), 6.95 (d, J = 1.9, 1 H), 6.86 (dd, J = 5.8, 2.0, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,700811-29-6, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/58176; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 700811-29-6, 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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine, molecular formula is C5H6ClN3, The 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.

To a solution of 1.4 g of (2-Chloro-pyridin-4-yl) -hydrazine (9.79 MMOL, 1.51 equiv) in 30 mL of NMP was added sequentially 2.0 g of N-CYANO-N – (4-ETHOXYCARBONYLPHENYL)-O- phenylisourea (6.45 MMOL, 1.00 equiv) and 10 mL of Hunig’s base. The resulting solution was warmed to 220 C via microwave irradiation for 6 min. The reaction mixture was poured into 100 mL of water and the resulting solid was filtered, yielding 3.0 g of a wet solid, which was dissolved in 40 mL of THF. To the stirred reaction mixture was added 1.50 g of nitrosonium tetrafluoroborate (12.9 MMOL, 2.0 equiv). Rapid bubbling was observed and stirring was continued for 1 hr. 4- [L- (2-CHLORO-PYRIDIN-4-YL)-LH [1, 2,4] TRIAZOL-3-YLAMINO]-BENZOIC acid ethyl ester was filted out of the reaction mixture, yielding 2.0 g (5.83 MMOL, 90.4 % yield) as a yellow SOLID. H NMR (500 MHz, DMSO-d6) 8 10.20 (1 H, s), 9.40 (1 H, s), 8.52 (1 H, d), 8.02 (1 h, s), 7.91 (3 H, m), 7.74 (2 H, d), 7.15 (1 H, br s), 4.27 (2 H, q), 1.31 (3 H, t) ppm. LC/MS : 3.64 min/344.01 (M+1).

According to the analysis of related databases, 700811-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LEDEBOER, Mark W.; DAVIES, Robert J.; WO2005/13982; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.700811-29-6, name is 2-Chloro-4-hydrazinopyridine, molecular formula is C5H6ClN3, molecular weight is 143.5742, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-4-hydrazinopyridine

5.25 g (13.3 mmol) of (7), 3.78 g (17.5 mmol) of (2-Chloro-pyridin-4-yl)-hydrazine and 13.3 ml (74.7 mmol) of DIEA were suspended in 26.6 ml of NMP. The reaction mixture was capped and heated to 220 degrees C. via microwave irradiation. After 6 min., the reaction mixture was allowed to cool to RT. The reaction mixture was then poured onto a saturated aqueous solution of sodium bicarbonate. This aqueous phase was diluted with EtOAc and the layers were separated. The organic was dried over MgSO4, filtered and evaporated to dryness. This crude material was chromatographed on 6 inches of silica gel and eluted with 5-9% MeOH/CH2Cl2. The still slightly crude material was recrystallized from EtOAc/Hexane. Yield: 1.38 g, approximately 23%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,700811-29-6, 2-Chloro-4-hydrazinopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Salituro, Francesco; Ledeboer, Mark; Ledford, Brian; Wang, Jian; Pierce, Albert; Duffy, John; Messersmith, David; US2006/63756; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine. A new synthetic method of this compound is introduced below., Safety of 2-Chloro-4-hydrazinopyridine

A solution of (2-chloro-pyridin-4-yl)-hydrazine (1.0 g, 6.965 mmol), ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate, INT1 (1.67 g, 6.965 mmol) and triethylamine (1.92 mL, 13.758 mmol) in ethanol (25 mL) was stirred overnight at 80 C. The reaction mixture was concentrated under reduced pressure and residue purified by chromatography over silica gel (gradient of EA in heptane from 0 to 25%) to afford the title compound as a clear oil (765 mg, 34%). 1H NMR (300 MHz, chloroform-d) delta 1.39 (t, J=7.2 Hz, 3H), 4.39 (q, J=7.2 Hz, 2H), 7.26 (s, OH), 7.36 (d, J=5.5 Hz, 1H), 7.51 (d, J=1.9 Hz, 1H), 8.16 (s, 1H), 8.57 (d, J=5.4 Hz, 1H). MS m/z 320 (MH+).

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, 700811-29-6, 2-Chloro-4-hydrazinopyridine.

Reference:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 700811-29-6, 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 700811-29-6 as follows.

Step 2: 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde To a solution of 1-(2-chlorophenyl)ethanone (1.08 mL, 8.36 mmol) in AcOH (33 mL) was added 2-chloro-4-hydrazinopyridine (1.20 g, 8.36 mmol). The reaction mixture was allowed to stir at rt for 1 h and was then diluted with water. A white precipitate formed, and the mixture was extracted with EtOAc several times. The organic solutions were combined, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated.The residue was dissolved in DMF (15 mL) and added to a solution of phosphoryl chloride (1.56 mL, 16.7 mmol) in DMF (13 mL) which had been stirring at rt for 30 min. The reaction mixture was allowed to stir at 80 C. for 18 h and then at rt for 35 h. The mixture was diluted with water and extracted several times with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde (1.95 g, 73%). LCMS (AA): m/z=318 (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,700811-29-6, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine. A new synthetic method of this compound is introduced below., Safety of 2-Chloro-4-hydrazinopyridine

A solution of (2-chloro-pyridin-4-yl)-hydrazine (1.0 g, 6.965 mmol), ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate, INT1 (1.67 g, 6.965 mmol) and triethylamine (1.92 mL, 13.758 mmol) in ethanol (25 mL) was stirred overnight at 80 C. The reaction mixture was concentrated under reduced pressure and residue purified by chromatography over silica gel (gradient of EA in heptane from 0 to 25%) to afford the title compound as a clear oil (765 mg, 34%). 1H NMR (300 MHz, chloroform-d) delta 1.39 (t, J=7.2 Hz, 3H), 4.39 (q, J=7.2 Hz, 2H), 7.26 (s, OH), 7.36 (d, J=5.5 Hz, 1H), 7.51 (d, J=1.9 Hz, 1H), 8.16 (s, 1H), 8.57 (d, J=5.4 Hz, 1H). MS m/z 320 (MH+).

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, 700811-29-6, 2-Chloro-4-hydrazinopyridine.

Reference:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 700811-29-6, 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 700811-29-6 as follows.

Step 2: 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde To a solution of 1-(2-chlorophenyl)ethanone (1.08 mL, 8.36 mmol) in AcOH (33 mL) was added 2-chloro-4-hydrazinopyridine (1.20 g, 8.36 mmol). The reaction mixture was allowed to stir at rt for 1 h and was then diluted with water. A white precipitate formed, and the mixture was extracted with EtOAc several times. The organic solutions were combined, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated.The residue was dissolved in DMF (15 mL) and added to a solution of phosphoryl chloride (1.56 mL, 16.7 mmol) in DMF (13 mL) which had been stirring at rt for 30 min. The reaction mixture was allowed to stir at 80 C. for 18 h and then at rt for 35 h. The mixture was diluted with water and extracted several times with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde (1.95 g, 73%). LCMS (AA): m/z=318 (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,700811-29-6, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 700811-29-6, 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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine. A new synthetic method of this compound is introduced below.

A microwave reaction vessel was charged with 1.34 g of (2-Chloro-pyridin-4-yl)-hydrazine (7.48 mmol, 1.1 equiv) and 2.00 g of N-cyano-N’-(4-acetamidophenyl)-O-phenylisourea (6.80 mMol, 1 equiv). The solids were dissolved in 40 mL of NMP and 8 mL of DIEA. The sealed vessel was warmed to 220 C. for 6 min via microwave irradiation. Upon cooling, the resulting solution was poured into 200 mL of saturated sodium bicarbonate. The precipitate was collected and washed with 3×100 mL of water. After azeotropic drying (3×50 mL of acetonitrile) the dark yellow solid (2.0 g, 5.80 mMol, 85% yield) was used without further purification. 1H NMR (500 Mhz, DMSO-d6) delta 9.68 (1 H, s), 9.00 (1 H, s), 8.40 (1 H, d), 7.67 (2 H, m), 7.50 (2 H, d), 7.40 (2 H, d), 6.95 (2 H, s), 2.0 (3 H, s) ppm. LCMS: 2.16 minutes/343.95 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,700811-29-6, 2-Chloro-4-hydrazinopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Salituro, Francesco; Ledeboer, Mark; Ledford, Brian; Wang, Jian; Pierce, Albert; Duffy, John; Messersmith, David; US2006/63756; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem