Month: April 2022

Electric Literature of 716362-10-6, 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 716362-10-6 as follows.

6-Chloro-4-methoxynicotinic acid (18) was prepared according to Ehara et al., ACS Med. Chem. Lett. 2014, 5, 787-792. To a suspension of this compound (3.87 g, 9.97 mmol) in oxalyl chloride (25 mL, 37 g, 291.5 mmol) was added DMF (0.8 mL) followed by anhydrous CH2C12(10 mL) and the reaction mixture was stirred 2 h at 60 C. Afterwards the reaction mixture was concentrated using the argon flow and the residue was dried under reduced pressure affording the respective chloroanhydride (4.0 g, 100% crude) which was immediately used for the next step.To a solution of this compound in hot EtOAc (100 mL) was added 2,3,5,6-tetrafluorophenol (2.92 g, 19.35 mmol; vigorous gas evolution was observed). Thereafter, the mixture was cooled to ambient temperature, Et3N (2.68 mL, 1.96 g, 19.35 mmol) was added dropwise and the resulting suspension was stirred for 1 h. Afterwards, the reaction mixture was washed with H20 (3 X20 mL), brine (2×20 mL), dried and concentrated under reduced pressure. The residue was taken up in CH2Cl2(70 mL), the suspension was filtered, the filter cake was washed with CH2Cl2(50 mL). The collected dichloromethane fraction was concentrated under reduced pressure. The residue was recrystallized from hexane affording 14 (2.6 g, 44%) as a colorless solid. The mother liquor was concentrated by reduced pressure and the residue was purified by column chromatography (CH2Cl2:hexane=8:2.5) giving the second crop of 14 (0.8 g, total 58%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,716362-10-6, its application will become more common.

Reference:
Patent; UNIVERSITAeT ZU KOeLN; NEUMAIER, Bernd; ZLATOPOLSKIY, Boris; KRAPF, Philipp; RICHARZ, Raphael; DRZEZGA, Alexander; (49 pag.)WO2019/175405; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1374655-69-2, 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. 1374655-69-2, name is 3-Bromo-4-ethyl-5-fluoropyridine, molecular formula is C7H7BrFN, 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.

A reaction vessel containing a mixture of 3-bromo-4-ethyl-5-fluoropyridine (0.25 g, 0.0012 mol), 4,4,4*,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (0.96 g, 0.0036 mol), and potassium acetate (0.36 g, 0.0036 mol) in 1,4-dioxane (15 mL) was purged with argon for 10 min. Next [l,l-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.09 g, 0.00012 mol) was added and heated at 100 C for 18 h. The reaction mixture was cooled to room temperature filtered through a bed of CELITE and the bed was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to afford the crude product 4-ethyl-3-fluoro-5-(4,4,5,5tetramethyl-l ,3,2-dioxaborolan-2-yl)pyridine. MS (M+l): 252.1.

According to the analysis of related databases, 1374655-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, D. Jonathan; CAI, Jaiqiang; CARSWELL, Emma; COOKE, Andrew; HOYT, Scott, B.; LONDON, Clare; MACLEAN, John; PARK, Min, K.; RATCLIFFE, Paul; XIONG, Yusheng; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2013/43521; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 119248-43-0, Adding some certain compound to certain chemical reactions, such as: 119248-43-0, name is 1H-Pyrrolo[3,2-c]pyridine-3-carboxylic acid,molecular formula is C8H6N2O2, 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 119248-43-0.

Example 218 (S)-(2,7-Dimethyl-3-(3,4,5-trifluorophenyl)-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)(1H-pyrrolo[3,2-c]pyridin-3-yl)methanone The title compound was prepared in a manner analogous to Example 288, using 1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid instead of 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid. MS (ESI): mass calcd. for C22H18F3N5O, 425.1; m/z found, 426.1 [M+H]+. 1H NMR (500 MHz, Methanol-d4) delta 8.98 (s, 1H), 8.24 (d, J=5.9 Hz, 1H), 7.82 (s, 1H), 7.52 (dd, J=5.8, 1.1 Hz, 1H), 7.35-7.27 (m, 2H), 5.66 (s, 1H), 4.52 (s, 1H), 3.82 (s, 3H), 3.50-3.36 (m, 1H), 2.94-2.84 (m, 1H), 2.60-2.50 (m, 1H), 1.65-1.60 (m, 3H).

According to the analysis of related databases, 119248-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2510-23-8 ,Some common heterocyclic compound, 2510-23-8, molecular formula is C7H5N, 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.

To a solution of D-l 3-ethyne pyridine (8.0 g, 77.6 mmol) in THF (ISOmL) at -78 C, n-BuLi (1,6 M in hexanes, 54 mL, 85,3 mmol) was added dropwise (keeping the reaction temperature below -60 C), It was stirred at this temperature for another 2 hrs and warmed up to OC. It was cooled to -30 C again and a fresh chopped dry ice was added. It was stirred and allowed to warm up to 0 C and 20 mL 4.ON NaOH was added. Organic layer was separated, Aqueous layer was acidified to ph <1, Solid was filtered to yield the final product. Yield: 6.0 g 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. 2510-23-8, 3-Ethynylpyridine, other downstream synthetic routes, hurry up and to see. Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2008/14311; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 89466-17-1, name is 6-Bromo-5-methylpyridin-2-amine, molecular formula is C6H7BrN2, 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. Product Details of 89466-17-1

6-bromo 5-methyl pyridin-2-amine (0.1 g) was dissolved in dichloromethane (1 mL) under nitrogen atmosphere. The solution was cooled to 0C and triethyl amine (0.149 mL) was added. 1 -(2,2-difluorobenzo[d][1 ,3]dioxol-5- yl)cyclopropane-1 -carbonyl chloride (0.209 g) in dichloromethane (0.5 mL) was added drop wise into the reaction mixture in 5 minutes. The reaction mixture was warmed to 30C and stirred for 18 hours at the same temperature. Quenched the reaction mixture with saturated potassium hydroxide solution (30 mL) and extracted with dichloromethane (30 mL). The organic solution was dried over sodium sulphate and evaporated under reduced pressure to afford crude product. The crude product was purified by column chromatography using 60-120 mesh and 10-20% ethyl acetate / hexane as eluent to obtain the title compound as brown color solid. Yield: 0.150 g; Purity by HPLC: 96.90%

With the rapid development of chemical substances, we look forward to future research findings about 89466-17-1.

Reference:
Patent; DR. REDDY?S LABORATORIES LIMITED; DAHANUKAR, Vilas Hareshwar; ORUGANTI, Srinivas; RAO, Pallavi; CHAKKA, Ramesh; BAIG, Mohammed Azeezulla; VYALA, Sunitha; SALADI, Venkata Narasayya; PEDDY, Vishweshwar; ELATI, Raviram Chandrasekhar; MOHANARANGAM, Saravanan; RAJ, Gopal; MAMIDIPALLI, Phani; (73 pag.)WO2017/175161; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51285-26-8, Adding some certain compound to certain chemical reactions, such as: 51285-26-8, name is Picolinimidamide hydrochloride,molecular formula is C6H8ClN3, 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 51285-26-8.

2-Pyridin-2-vl-3H-pyrimidin-4-one; Pyridine-2-carboxamidine hydrochloride (1.0 g, 6.5 mmol), sodium (lE)-3-ethoxy-3-oxoprop-l- en-1-olate (3.5 g, 25 mmol) and sodium ethoxide (0.45 g, 6.5 mmol) were added to ethanol (50 mL, 99.5 %) and the reaction mixture was refluxed under nitrogen atmosphere for 18 h, filtered hot and concentrated. The residue was dissolved in water (20 mL), neutralised with hydrochloric acid (1 M) and purified with reversed phase preparative HPLC This gave 0.68 g (60 %) of the title compound. ‘H NMR (400 MHz, dmso-d6) 8 12.07 (br s, 1 H), 8.73 (m, 1 H), 8.29 (m, 1 H), 8.06-7. 97 (m, 2 H), 7.63 (m, 1 H), 6.34 (d, J=6. 8 Hz, 1 H).

According to the analysis of related databases, 51285-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2005/82884; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 103058-87-3 ,Some common heterocyclic compound, 103058-87-3, molecular formula is C7H6BrNO2, 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.

5-Bromo-2-methoxynicotinaldehyde (472 mg, 2.18 mmol) and 1-methylpiperidin-4- amine (249 mg, 2.18 mmol) were stirred in methanol (10 mL). Acetic acid (0.12 mL) and sodium cyanoborohydride (137 mg, 2.18 mmol) were then added and the mixturewas stirred at room temperature for 22 h. The reaction mixture was evaporated under reduced pressure and the residue was partitioned between dichloromethane and a saturated aqueous sodium hydrogen carbonate solution. The phases were separated. The aqueous layer was extracted with dichloromethane. The combined organics were dried over anhydrous magnesium sulphate, filtered and evaporated under reducedpressure to give 647 mg (94% yield) of the title compound.LRMS (M+1): 314, 3161H NMR (400 MHz, Chloroform-d) 6 ppm 1.44 (2H, m), 1.88 (2H, m), 2.26 (3H, s), 2.43(1 H, m), 2.81 (2H, m), 3.73 (2H, s), 3.93 (3H, s), 7.69 (1 H, d, J = 2.4 Hz), 8.08 (1 H, d, J= 2.4 Hz)

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. 103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMIRALL, S.A.; GRACIA FERRER, Jordi; ERRA SOLA, Montserrat; WO2015/91532; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4487-56-3 , The common heterocyclic compound, 4487-56-3, name is 2,4-Dichloro-5-nitropyridine, molecular formula is C5H2Cl2N2O2, 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.

2,4-Difluoro-5-nitropyridine.In a 250 mL round-bottom flask was added 2,4- dichloro-5-nitropyridine (0.73 g,3.8 mmol), potassium fluoride (0.659 g, 11.3 mmol), and 18-crown-6 (0.160 g,0.605 mmol) in N-methylpyrrolidinone (3 mL) to give a tan suspension. Themixture was heated at 100C under nitrogen for 3 h. The mixture was thenpartitioned between water and ether/hexane. The organic layer was washed withwater, brine, dried and concentrated to give a tan solid (0.515 g, 85%): 1H NMR(400 MHz, CDC13) delta 9.07 (d, J = 9.7 Hz, 1H), 6.96 (dd, J = 9.5, 2.5 Hz,1H);19F NMR (376 MHz, CDC13) delta -52.20 (d, J = 29.3 Hz), -98.13 (d, J = 28.9 Hz).

The synthetic route of 4487-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, 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 73406-50-5.

Intermediate 8. S-Trifluoromethanesulfonyloxy-pyridine^-carboxylic acid ethyl ester.; To a stirred solution of 3-hydroxy-pyridine-2-carboxylic acid ethyl ester (3.06 g, 20.0 mmol) and Et3N (triethylamine) (5.58 ml_, 40.0 mmol) in CH2CI2 (100 mL) at minus150C was added a solution of Tf2O (trifluoromethanesulfonic anhydride) (4.04 mL, 24.0 mmol) in CH2CI2 (10 mL). The reaction was stirred at this temperature for 1 hour and then CH2CI2 (100 mL) was added followed by H2O. The layers were separated and the organic EPO layer was washed three times with 30 ml H2O and twice with 30 ml brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica chromatography using a gradient of hexanes:EtOAc (100:0) to hexanes-.EtOAc (75:25) to yield 13.3 g (74.52%) of Intermediate 8 as a yellow oil.

According to the analysis of related databases, 73406-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/31828; (2007); A2;,
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.62150-46-3, name is 4-Bromopicolinamide, molecular formula is C6H5BrN2O, molecular weight is 201.0207, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5BrN2O

EXAMPLE 64-((4-Oxo-3-o-tolyl-3,4-dihydropyrrolo[1 ,2-tf[1 ,2,4]triazin-2- yl)methylamino)picolinamideA mixture of 2-(aminomethyl)-3-o-tolylpyrrolo[1 ,2-7[1 .2,4]triazin-4(3H)-one (102 mg, 0.4 mmol), 4-bromopicolinamide (105 mg, 0.52 mmol) and DIEA (200 mu, 1 .13 mmol) in n- butanol (2.2 mL) was reacted under microwave irradiation at 190C during 22 h. After cooled to room temperature, the mixture was concentrated in vacuum and was purified by reverse phase chromatography (C-18 silica from Waters, water/1 :1 acetonitrile- methanol as eluents [0.1 % v/v formic acid buffered] 0% to 100%) to obtain 7 mg of the title compound (4,6%).LRMS (m/z): 375 (M+1 )+.1H NMR (400 MHz, DMSO) delta 8.38 (s, 2 H), 8.01 (d, J=5.86 Hz, 1 H), 7.90 (m, 1 H), 7.61 – 7.73 (m, 1 H), 7.48 – 7.58 (m, 1 H), 7.39 – 7.48 (m, 1 H), 7.23 – 7.40 (m, 2 H), 7.03 – 7.14 (m, 1 H), 6.93 – 7.04 (m, 1 H), 6.62 (dd, J=4.30, 2.74 Hz, 1 H), 6.38 – 6.53 (m, 1 H), 3.86 – 3.99 (m, 2 H), 2.08 (s, 3 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62150-46-3, 4-Bromopicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem