Tag: M.W:100-200

Reference of 62135-58-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 62135-58-4, name is Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Example 1243-([1,2,4]Triazolo[1,5-a]pyridin-2-ylethynyl)-7,7-dimethyl-7,8-dihydroquinolin- 5(6H)-one[00340]Ethyl [1 ,2,4]triazolo[1 ,5-a]pyridine-2-carboxylate {Tetrahedron, 1986, 42 (10), pp 2625-2634), (56 mg, 0.3 mmol) is dissolved in 7 mL of dry DCM, and the solution is cooled to 0 C. DIBAL-H (1 .2 M solution in toluene, 2.2 mL, 2.7 mmol) is added dropwise. The reaction mixture is allowed to warm to r.t and then stirred overnight. A solution of sodium potassium tartrate and water are added, and the mixture is extracted with DCM. The organic phase is dried over Na2S04, filtrated and evaporated to give 85 mg (58%) of [1 ,2,4]triazolo[1 ,5-a]pyridin-2-ylmethanol as brown solid. [00341 ]Oxalylchloride (0.15 ml, 1 .7 mmol) is dissolved in 8 mL of DCM, the mixture is cooled to -78 C and DMSO (0.24 mL, 3.4 mmol) is added, followed by dropwise addition of a solution of [1 ,2,4]triazolo[1 ,5-a]pyridin-2-ylmethanol (85 mg, 0.3 mmol) in DCM (5 mL). The reaction mixture is stired for 30 min at -78 C, then TEA (0.96 mL, 6.8 mmol) is added, and the mixture is alowed to warm to r.t. The mixture is then treated with brine and extracted with DCM. The organic phase is dried over Na2S04, filtrated and evaporated to give 196 mg of crude [1 ,2,4]triazolo[1 ,5-a]pyridine-2-carbaldehyde which is used in the next step without further purification.[00342][1 ,2,4]Triazolo[1 ,5-a]pyridine-2-carbaldehyde (149 mg, 1 mmol) is dissolved in 8 mL of MeOH, K2C03 (280 mg, 2 mmol) is added, and the solution is cooled to 0 C. Dimethyl-1 -diazo-2-oxopropylphosphonate (Bestmann-Ohira reagent) (0.15 mL, 1 mmol) is added, and the reaction mixture is warmed to r.t. and stirred for 3 h, then evaporated to dryness. The residue is treated with water, extracted with CHCI3 and the organic phase is dried over Na2S04, filtered and evaporated. The residue is purified by flash column chromatography on silica to give 80 mg (54%) of 2-ethynyl- [1 ,2,4]triazolo[1 ,5-a]pyridine as yellowish solid.[00343]According to General Procedure 1 , 3-bromo-7,7-dimethyl-7,8-dihydroquinolin- 5(6/-/)-one (53 mg, 0.21 mmol) is reacted with 2-ethynyl-[1 ,2,4]triazolo[1 ,5-a]pyridine (30 mg, 0.21 mmol) in the presence of PdCI2[PPh3]2 (7 mg, 0.01 mmol), Cul (2 mg, 0.01 mmol) and TEA (0.1 mL) in DMF (1 .5 mL) at 50 C for 16 h. The crude product is purified by column chromatography (silica gel, EtOAc/hexanes) to provide the title compound (17 mg, 26%).1H NMR (CDCI3), deltaEta, 1 .13 (s, 6H), 2.58 (s, 2H), 3.08 (s, 2H), 7.1 1 (t, 1 H), 7.59 (t, 1 H), 7.76 (d, 1 H), 8.48 (d, 1 H), 8.58 (d, 1 H), 8.94 (d, 1 H).LC/MS (M+H)+ = 317

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 62135-58-4, Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; ABEL, Ulrich; MULLER, Sibylle; KUBAS, Holger; MEYER, Udo; HECHENBERGER, Mirko; KAUSS, Valerjans; ZEMRIBO, Ronalds; WO2012/52451; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 22353-40-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 22353-40-8, name is 2,3-Dichloro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2C 5-amino-2,3-dichloropyridine Anhydrous SnCl2 (300 g, 1.58 mol) and concentrated HCl (350 mL) were charged to a 5 L flask with mechanical stirrer and thermocouple. The flask was cooled in ice and the product of Example 2B (100 g, 0.518 mol) was added in portions maintaining the temperature below 65 C. After the addition was complete, the cold bath was removed, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled in ice as 25% aqueous NaOH (1000 mL) was added to bring the mixture to pH >10. The mixture was extracted with CH2Cl2 (1*600 mL, 2*400 mL) and the combined extracts were washed with brine (200 mL), dried (MgSO4), and concentrated under vacuum. The residual solid was crystallized from a mixture of water (500 mL) and ethanol (100 mL) to provide the title compound as a solid. 1H NMR (CDCl3, 300 MHz) delta 3.80 (br s, 2H), 7.10 (d, J=3 Hz, 1H), 7.77 (d, J=3 Hz, 1H); MS (DCI/NH3) m/z 180/182/184 (M+NH4)+163/165/167 (M+H)+.

According to the analysis of related databases, 22353-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2004/242641; (2004); 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.98139-15-2, name is 4-Aminopicolinonitrile, molecular formula is C6H5N3, molecular weight is 119.124, as common compound, the synthetic route is as follows.SDS of cas: 98139-15-2

Methyl 4-(tert-butylsulfamoyl)-3-chloro-l -methyl -pyrrole-2-carboxylate (50 mg, 0.16 mmol) and 4-aminopyridine-2-carbonitrile (0.021 g, 0.18 mmol) were dissolved in THF (5 mL) and cooled in an ice bath. To this was added dropwise lithium bis(trimethylsilyl)amide in toluene (0.32 mL, 1 M, 0.32 mmol) over a period of 5 minutes. The resulting mixture was allowed to reach room temperature and was stirred for 3 hours. The resulting mixture was quenched using ammonium chloride (10 mL / aq. sat.). This was extracted using ethylacetate (3 X 20 mL). The combined extracts were washed with brine (20 mL), dried on Na2S04, filtered and concentrated in vacuo. The obtained crude was purified by silica gel column chromatography using gradient elution from heptane to iPrOH. (100:0 to 70:30). The desired fractions were concentrated in vacuo and dried in a vacuum oven at 55 C for 24 hours yielding compound 6 (10 mg) as a bright white powder. Method B; Rt: 0.91 min. m/z : 394.0 (M-H)~ Exact mass: 395.1. 1H NMR (0198) (400 MHz, DMSO-d6) delta ppm 1.18 (s, 9 H), 3.79 (s, 3 H), 7.38 (s, 1 H), 7.65 (s, 1 H), 7.90 (dd, J=5.6, 2.1 Hz, 1 H), 8.20 (d, J=2.0 Hz, 1 H), 8.63 (d, J=5.5 Hz, 1 H), 10.97 (br. s., 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886374-01-2 , The common heterocyclic compound, 886374-01-2, name is 5-Chloro-3-fluoro-2-methoxypyridine, molecular formula is C6H5ClFNO, 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 stirred mixture of 5-chloro-3-fluoro-2-methoxypyridine (0.33 g, 2.0 mmol), bis(pinacolato)diboron (0.58 g, 2.3 mmol), [l,l-bis(diphenylphosphino)- ferrocene]palladium(II) chloride, complex with DCM (0.17 g, 0.21 mmol), and potassium acetate (0.61 g, 6.17 mmol) in dry 1,4-dioxane (8.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to and monitored with LC-MS and TLC. After 21 h, the reaction was cooled to rt then filtered through Celite. The organic solvent was removed under reduced pressure, and the black residue was identified as 3-fluoro-2- methoxy-5-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)pyridine and used without purification. Mass Spectrum (pos.) m/e: 254.0 (M+H)+.

The synthetic route of 886374-01-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10273-89-9 ,Some common heterocyclic compound, 10273-89-9, molecular formula is C12H11N, 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.

General procedure: Unless otherwise stated, in an Argon filled glove-box a crimp-cap microwave vial equipped with a magnetic stirring bar was charged with the appropriate cyclometalated Ru(ll)-catalyst (like Ru1-Ru46, from 3 mol % to 10 mol %), KOAc (5.9 mg, 0.06 mmol, 30 mol %), K2CO3 (2.0 – 4.0 equiv.), the appropriate DG-containing arene (like N1-N12, 0.20 mmol, 1.0 equiv.), the appropriate (hetero)aryl (pseudo)halide (like X1-X42, 0.2 mmol, 1.0 equiv) and /V-methyl-2- pyrrolidone (NMP) (200 pL, 1 M). The vial was capped and stirred at 35 C for 24 hours. Upon completion, the crude mixture was loaded on a silica gel column and purified by flash chromatography

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10273-89-9, its application will become more common.

Reference:
Patent; THE UNIVERSITY OF MANCHESTER; LARROSA, Igor; SIMONETTI, Marco; CANNAS, Diego Maria; (94 pag.)WO2019/215426; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 71670-70-7, 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. 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride, molecular formula is C7H9Cl2N, 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.

Example 101 l-(2-(l -hydroxycyclopropyl)ethyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)- 8-(3-(trifluoromethoxy)phenoxy)-lH-purine-2,6(3H,7 -dione To a solution of l -(2-(l-hydroxycyclopropyl)ethyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)- l H-purine- 2,6(3H,7H)-dione (50 mg, 0.1 17 mmol, intermediate 58) in DMF (3 mL) was added 2-(chloromethyl)-5-methylpyridine hydrochloride (24.9 mg, 0.176 mmol, intermediate 50), followed by potassium carbonate (48.6 mg, 0.351 mmol) and TBAI ( Omg, 0.027mmol). The reaction was stirred at 65 C overnight. The reaction was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by preparative HPLC to give l-(2-(l – hydroxycyclopropyl)ethyl)-3-methyl-7- ((5-methylpyridin-2-yl)methyl)-8-(3- (trifluoromethoxy)phenoxy)-lH-purine-2,6(3H,7H)-dione (21 mg, 33.7% yield) as white solid. ‘H-NMR (CD3OD) 6 8.320-8.315(d, lH), 7.662-7.636(d,lH), 7.561-7.517(t,lH), 7.363- 7.315(m,3H), 7.240-7.215(m,lH), 5.608(s,2H), 4.247-4.212(t,2H), 3.462(s,3H), 2.338(s,3H), 1.829-1.793(t,2H), 0.582-0.554(m, 2H), 0.370-0.340(m, 2H). LCMS retention time 2.869 min; LCMS MH+ 532.

According to the analysis of related databases, 71670-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertrand; GALLASCHUN, Randall; WO2014/143799; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67310-56-9 ,Some common heterocyclic compound, 67310-56-9, molecular formula is C7H7NO2, 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.

f) 1-(5-Methoxymethoxy-pyridin-2-yl)-ethanoneNaH was added to a solution of 1 g (7.29 mmol) 1-(5-hydroxy-pyridin-2-yl)-ethanone (Anichem) in 15 ml DMF at 0 C. After stirring this mixture for 1 h, 0.78 ml (8.75 mmol) MOMCl was added at 0 C. Then the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was poured on water and extracted 2 times with EtOAc. The combinded organic layers were washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel (EtOAc, heptane) to yield 1.12 g of the pure title compound as an oil. LCMS (method L): tR=0.66 min, M+H=182.

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. 67310-56-9, 1-(5-Hydroxypyridin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; US2011/3786; (2011); 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. 183428-91-3, name is 2-Amino-3-methyl-5-cyanopyridine, molecular formula is C7H7N3, 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. COA of Formula: C7H7N3

EXAMPLE 17 (E)-6-((4-Amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)quinazolin-2-yl)amino)-5- methylnicotinonitrile- Compound 17 Synthesis of (£)-6-((4-amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)quinazolin-2- yl)amino)-5-methylnicotinonitrile (compound 17) [0281] Compound 2a (20 mg, 0.06 mmol), 6-amino-5-methylnicotinonitrile (24 mg, 0.18 mmol, Ark Pharm Inc, AK-25043), N,N-diisopropylethylamine (622 mg, 0.48 mmol), (9,9- dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4 mg, 0.006 mmol) and palladium (II) acetate (1 mg, 0.006 mmol) were combined under argon in N-methyl-2-pyrrolidone (1 mL). The reaction was heated at 120C in a sealed vessel for 4 hours. The reaction mixture was cooled down to room temperature and diluted with water and ethyl acetate. The organic layer was separated and washed twice with brine, dried over magnesium sulfate and this solution was filtered through a 2 cm layer of silica gel which was washed with additional ethyl acetate. Combined organics were concentrated down under reduced pressure. The crude residue was treated with diethyl ether in the sonic bath for 5 minutes. The solid compound was filtered off and washed twice with diethyl ether and once with hexane to afford the title compound 17. *H NMR (400 MHz, DMSO-Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 138588-22-4, 3-(Pyridin-2-yl)-1,2,4-thiadiazol-5-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, 138588-22-4, blongs to pyridine-derivatives compound. Product Details of 138588-22-4

3-Pyridin-2-y]-[l ,2,4]thiadiazol-5-ylamine (50 mg, 0.28 mmol), 4~phenoxybenzoic acid (120 mg, 0.56 mmol), and l -[is(dimethyiamino)methylene]-lH-l,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (128 mg, 0.34 mmol) was placed in a vial. Then dissolved in DMF (3 mL, anhydrous), added N,N-diisopropylet ylamine (98 ,uL, 0.56 mmol), and stirred at 50 C for 16 h. The reaction was diluted with water and extracted with EtOAc (x 3). The combined organic layers were dried and concentrated onto celite. Purified by normal phase chromatography (solvent A CC12, solvent B CH2Cl2/MeOH. NH4OH 90: 10: 1, gradient from 0 – 50% B). Collected the desired product (25.2 mg, 0.0674 mmol, 24%). JH NMR (400 MHz, DMSO-t e) 6 ppm 7.1 1 (d, J-8.83 Hz, 2 H) 7.16 (d, J-7.66 Hz, 2 H) 7.23 – 7.31 (m, 1 H) 7.43 – 7.56 (m, 3 H) 7.98 (td, J=7.75, 1.73 Hz, i H) 8.24 (d, J-8.74 Hz, 3 H) 8.72 (d, J=4.34 Hz, 1 H) 13.71 (br. s., 1 H); LCMS (M/Z): M-H-f 375.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,138588-22-4, its application will become more common.

Reference:
Patent; SCYNEXIS INC.; LIU, Hao; SLIGAR, Jessica, Marie; SPEAKE, Jason, Daniel; MOORE, Joseph, A., III; BECK, Brent, Christopher; WO2015/73797; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 823-61-0, 3,6-Dimethyl-2-pyridinamine, 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, Safety of 3,6-Dimethyl-2-pyridinamine, blongs to pyridine-derivatives compound. Safety of 3,6-Dimethyl-2-pyridinamine

a) 5-Chloro-3,6-dimethylpyridin-2-amine NCS (3.28 g, 24.6 mmol, Eq: 1.00) was added at 15 C in one portion to a solution of 3,6-dimethylpyridin-2-amine (3 g, 24.6 mmol, Eq: 1.00) in ethyl acetate (130 mL). The temperature was maintained between 20-24 C for 1 h. The red mixture was stirred overnight. The mixture was filtered. The filtrate was washed with 40% aq. sodium bisulfite solution (100 ml) and brine. The aqueous phase was extracted with EtOAc (2×100 ml). The combined organic layers were dried over Na2S04 and then concentrated to an oil. The residue was purified by column chromatography (70g Si02, 0 to 50% EtOAc/n-heptane) to afford 5-chloro-3,6-dimethylpyridin- 2-amine (1.16 g, 30.2 %) as a light yellow-brown product. MS: m/z = 157.1 (M+H+)

The synthetic route of 823-61-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KUHN, Bernd; LERNER, Christian; RUDOLPH, Markus; SCHAFFHAUSER, Herve; WO2013/178572; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem