Pyridine-derivatives

Synthetic Route of 5346-38-3 ,Some common heterocyclic compound, 5346-38-3, molecular formula is C6H6N2S, 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 25 mL N,N-dimethyl formamide (DMF) containing alpha-b r omo a c e t o p heno n e ( 1 . 1 g , 5 . 5 m m o l ) , 2-pyridinecarbothioamide (760 mg, 5.5 mmol) was added.After kept stirring for 24 h, the reaction mixture was diluted with 200 mL EtOAc followed by washing with brine. Theorganic layer was dried over anhydrous Na2SO4 and evaporatedunder reduced pressure. Separation through flash columnchromatography using a mixture of n-hexane andEtOAc as eluents provided a white solid as the product. Yield: 81.0 %. Mp: 72-73 C. IR (film, cm-1): 3111, 3057,1576, 1499, 1462, 1461, 1273, 1240, 1065, 993, 781, 740,683. 1H NMR (CDCl3, 300 MHz, ppm) delta = 7.37-7.39 (m,2H), 7.46-7.51 (m, 2H), 7.63 (s, 1H), 7.83-7.88 (m, 1H), 8.03(d, 2H, J = 7.0 Hz), 8.36 (d, 1H, J = 7.8 Hz), 8.58 (d, 1H,J = 4.6 Hz).13C NMR (CDCl3, 75 MHz, ppm) delta = 115.3,119.9, 124.5, 126.4, 128.2, 128.8, 134.5, 137.1, 149.5,151.5, 156.7, 168.8. Anal. Calcd. (%) for C14H10N2S: C70.56, H 4.23, N 11.76. Found: C 70.48, H 4.31, N 12.01.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5346-38-3, its application will become more common.

Reference:
Article; Yang, Ming-Yang; Zhao, Xiao-Long; Zheng, Ming-Hua; Wang, Yue; Jin, Jing-Yi; Journal of Fluorescence; vol. 26; 5; (2016); p. 1653 – 1657;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2002-04-2, 5-(Pyridin-4-yl)-1,3,4-thiadiazol-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, 2002-04-2, blongs to pyridine-derivatives compound. name: 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine

A solution of (i?)-3-methoxy-4-(l-phenyl-2-((triisopropylsilyl)oxy)ethoxy)benzoic acid (0.1.0 g, 2.2 mmol, 1 eq.), 5-(4-pyridyl)-l,3,4-thiadiazol-2-yl amine (0.467g, 2.6 mmol, 1.2 eq.), HATU (1.35 g, 3.5 mmol, 1.5 eq.) and diisopropylethylamine (480 mu^, 2.75 mmol, 1.2 eq.) in NMP (10 mL) was stirred at 70 C for 16 hours. The cooled reaction mixture was added to water (100 mL) and the crude product filtered and partitioned between dichloromethane (100 mL) and water (15 mL). The layers were separated and the aqueous extracted with a mixture of dichloromethane (100 mL) and methanol (10 mL). The combined extracts were dried with magnesium sulfate, evaporated in vacuo and purified by silica gel column chromatography using a 20 – 100 % ethyl acetate in iso- exane gradient to afford (R)-3 -methoxy-4-(l -phenyl-2-((triisopropylsilyl)oxy)ethoxy)-N-(5-(pyridin-4-yl)- l,3,4-thiadiazol-2-yl)benzamide as a white solid (0.784 g, 60% yield). NMR (400 MHz, DMSO) 13.16 (IH, s), 8.79 (2H, dd, J=1.6, 4.5 Hz), 7.99 (2H, dd, J=1.6, 4.4 Hz), 7.84 (IH, d, J=2.0 Hz), 7.68 (IH, dd, J=2.1, 8.6 Hz), 7.52 – 7.48 (2H, m), 7.40 (2H, dd, J=7.6, 7.6 Hz), 7.37 – 7.32 (IH, m), 7.09 (IH, d, J=8.9 Hz), 5.62 (IH, dd, J=4.5, 6.5 Hz), 4.14 (IH, dd, J=6.8, 10.6 Hz), 4.00 (IH, dd, J=4.5, 10.8 Hz), 3.97 (3H, s), 1.15 – 1.08 (3H, m), 1.07 – 1.02 (18H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2002-04-2, its application will become more common.

Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 116632-24-7, 2-Amino-4,6-dichloropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 4,6-dichloropyridin-2-amine (2.0 g, 12.3 mmol), ethynylbenzene (2.51 g, 24.5 mmol), copper(I) iodide (234 mg, 1.23 mmol), Dichlorobis(triphenylphosphine)- palladium(II) (1.0 g, 1.23 mmol) and triethylamine (4.3 ml, 31 mmol) is stirred under argon atmosphere in ACN (20 ml) with THF (10 ml) for 6 h at 90C. The mixture is diluted with water and extracted with EtOAc. The combined organic layers are dried over MgS04, concentrated in vacuo and the product purified by NP chromatography. Yield: 1.2 g (43%). HPLC-MS: M+H=229; tR=l .96 min (*Method_2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116632-24-7, 2-Amino-4,6-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; BADER, Gerd; SPEVAK, Walter; STEFFEN, Andreas; PARKES, Alastair L.; WO2013/127729; (2013); A1;,
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. 5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, 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 5470-70-2

250mL single-neck flask was added methyl 6-methylpyridine-3-carboxylate (10g, 66.15mmol) and 1,4-dioxane (100mL), was added under stirring selenium dioxide (14.7g, 132mmol), nitrogen heated to 85 under the protection of the reaction overnight. Cooling to room temperature, filtered, and the solvent was removed by rotary evaporation, the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1), give a pale yellow solid 1.6g, Yield: 15percent.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Wang, Xiaojun; Yang, Xinye; Zhou, Pingjian; Yang, Chuanwen; Lin, Jihua; Xiong, Shaohui; Zhang, Yingjun; Xiao, Ying; Wang, Hui; Cao, Shengtian; Wu, Fangyuan; Ouyang, Luo; (74 pag.)CN105524053; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133081-24-0, Adding some certain compound to certain chemical reactions, such as: 133081-24-0, name is 6-Hydrazinylnicotinic acid,molecular formula is C6H7N3O2, 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 133081-24-0.

A solution of DOTA tri-t-butyl ester (225 mg, 0.393 mmol), HOBt (50 mg, 0.33 mmol), and EDC (62 mg, 0.32 mmol) in 50:50 dichloromethane:acetonitrile (2.0 mL) was stirred at ambient temperatures under nitrogen for 5 minutes, and treated with 6-hydrazinictoic acid (50 mg, 0.32 mmol). The solution was stirred for 60 hours and concentrated under reduced pressure. The residue was purified by HPLC on a Phenomenex Luna Cl 8 column (21.2 x 250 mm) using a 0.9%/min gradient of 9 to 36% acetonitrile containing 0.1% TFA at a flow rate of 20 niL/min. The main product peak eluting at 32.9 minutes was lyophilized to give the title compound as an off-white solid (3.0 mg, 1.0%). MS (ESI): 708.4 (60, M+H).

According to the analysis of related databases, 133081-24-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB PHARMA COMPANY; WO2007/5491; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5470-70-2, 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.5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

[01 10j To a solution of methyl 6-methylnicotinate (0.5 g, 3.31 mmol) in carbon tetrachloride (15 mL) was added N-bromosuccinimide (0.647 g, 3.63 mmol) followed by azobisisobutyronitrile (0.054 g, 0.33 mmol). The reaction mixture was heated at 75 C for 18 h. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by silica gel column chromatography, using 50% ethyl acetate in hexane to afford methyl 6- (bromomethyl)nicotinate (0.28 g, 37% yield) as a brownish solid. Calculated M+H: 229.97; Found M+H: 230.01.

Statistics shows that 5470-70-2 is playing an increasingly important role. we look forward to future research findings about Methyl 6-methylnicotinate.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1335210-23-5, 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 1335210-23-5 as follows.

Examples 9 and 10 Preparation of Compounds 9 and 1Theta (2S,5R,13aS)-N-((R)-H4-fluoroph^ octahydro-2,5-methanopyrido[ 1 ‘,2′:4,5]pyrazino[2, 1 -b][ 1 ,3]oxazepine- 10-carboxamide 9 and (2R,5S,13aR)-N-((R)-l-(4-fj.uorophenyl)ethyl)-8-hydroxy-7,9-dioxo- 2,3,4,5 J,9,13,13a-octahydro-2,5-methanopyrido[r,2’:4,5]pyrazino[2, b] [ 1 ,3]oxazepine- 10-carboxamide 10 Step 1 l-(2,2-dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-l ,4- dihydropyridine-3-carboxylic acid (1-A, 0.500 g, 1.59 mmol), was suspended in acetomtrile (6 rnL) and treated with N,N-diisopropylethylamine (DIPEA) (0.550 mL, 3.17 nifflol), (R)-l-(4-fluoropbenyi)ethanamine (0.242 rng, 1.74 mmol) and HATXJ (0.661 g, 1.74 mmol). The reaction mixture was stirred for 2 hours and partitioned between ethyl acetate and water. The organic layer was separated and washed with HCl ( 10% aq), sodium bicarbonate (1 M aq), dried over sodium sulfate, filtered and concentrated to afford crude (R)-methyl l -(2,2-dimethoxyethyl)-5-(l -(4- fiuorophenyl)ethylcarbamoyl)-3-methoxy-4-oxo-l ,4-dihydropyridine-2-carboxylate which was used without purification in the next step: LCMS-ESI+ (m/z): [M+H] ; calculated for C”.< ; i ^ X -()··: 437.17; found: 437.1. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1335210-23-5, its application will become more common. Reference:
Patent; GILEAD SCIENCES, INC.; JIN, Haolun; LAZERWITH, Scott, E.; MARTIN, Teresa, Alejandra, Trejo; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; CAI, Zhenhong, R.; PYUN, Hyung-Jung; MORGANELLI, Philip, Anthony; JI, Mingzhe; TAYLOR, James, G.; CHEN, Xiaowu; MISH, Michael, R.; DESAI, Manoj, C.; WO2014/100323; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1101120-05-1, 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. 1101120-05-1, name is 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, molecular formula is C9H5N3O, 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.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

According to the analysis of related databases, 1101120-05-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66572-56-3, Adding some certain compound to certain chemical reactions, such as: 66572-56-3, name is 2-Bromoisonicotinic acid,molecular formula is C6H4BrNO2, 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 66572-56-3.

A solution of 2-bromoisonicotinic acid (5.00 g, 24.8 mmol) in MeOH (50 mL) was treated with sulfuric acid (0.50 mL, 9.4 mmol) and the reaction mixture was stirred at 80 C for 1 hour. The mixture was returned to room temperature and stirred for a further 96 hours before heating to 80 C and stirring for 24 hours. The reaction mixture was cooled to room temperature, and the volatiles were removed in vacuo. An aqueous NaOH solution (2 M, -50 mL) was added to the residue and the aqueous was extracted with EtOAc (3 * 50 mL). The organic layers were combined, washed with brine, dried (MgS04) and the solvent removed in vacuo to give the title compound as a yellow oil (4.14 g, 77%). LCMS-B: rt 3.55 min; m/z 216 [Mu+Eta for /9Br. 218 [M+H]+ for 81 Br; 1H NMR (400 MHz, CDCb) delta 8.52 (dd, J = 5.0, 0.8 Hz, 1 H), 8.04 (t, J = 1.2 Hz. 1 H), 7.80 (dd, J = 5.0, 1.4 Hz, 1 H), 3.96 (s, 3H).

According to the analysis of related databases, 66572-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LTD; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; WALKER, Scott Raymond; LAGIAKOS, H. Rachel; (98 pag.)WO2016/34675; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 100367-39-3, 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. 100367-39-3, name is 4-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, 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.

4-BromoBromo-2-methoxypyridine (3.06 g, 16.2 mmol), (6- (trifluoromethyl)pyridin-3-yl)methanol (2.74 g, 15.5 mmol), 3,4,7,8- tetramethylphenanthroline (0.36 g, 0.15 mmol), CuI (0.14 g, 0.74 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were combined in toluene (15 mL) and heated to reflux under a nitrogen Attorney’s Docket 2882.023B atmosphere for 16 h. Upon cooling the mixture was purified by flash column chromagraphy (silica gel, hexanes/EtOAc, 1 :0 to 1 :1) to provide the title compound (3.19 g, 72%) as a red oil: 1H NMR (300 MHz, CDCl3) delta 8.78 (s, IH), 8.02 (d, J= 5.9 Hz, IH), 7.95 (d, J= 8.1 Hz, IH), 7.32 (d, J= 8.0 Hz, IH), 6.55 (dd, J= 5.9, 2.2 Hz, IH), 6.26 (d, J = 2.2 Hz, IH), 5.16 (s, 2H), 3.93 (s, 3H).

According to the analysis of related databases, 100367-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem