Month: April 2022

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

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

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

Synthetic Route of 1111637-74-1, 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.1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, molecular formula is C7H5BrFNO, molecular weight is 218.02, as common compound, the synthetic route is as follows.

A solutioa of the above compouad (160.0 mg, 0.73 mmol, .0 eq.) and meftjyihydrazme ( 193.2 uL, 3.67 mmol, 3,0 eq.) in l-butaaol (2,5 niL) was heated to 1.50 C in a microwave reactor for 45 mm. The reaction mixture was cooled to rt and concentrated under reduced pressure. The residue was purified using flash chromatography (0-40% EtOAc/hexanes) to provide the title compound (3) as a pale yellow solid (150 nig, 90,4% yield). ES-M.S M?l f : 228.2.

The chemical industry reduces the impact on the environment during synthesis 1111637-74-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P. Jeffrey; HOPKINS, Corey R.; LINDSLEY, Craig W.; NISWENDER, Colleen M.; ENGERS, Darren W.; PANARESE, Joe; BOLLINGER, Sean; ENGERS, Julie; BRONSON, Joanne; WU, Yong-Jin; GUERNON, Jason; (180 pag.)WO2016/123629; (2016); 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. 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone, molecular formula is C12H8ClNO, 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. Recommanded Product: (4-Chlorophenyl)(pyridin-2-yl)methanone

To a stirred solution of (4-chlorophenyl) (pyridin-2-yl) methanone (3.5 g, 16.12 mmol) in MeOH (35 mL) under argon atmosphere was added hydroxyl amine hydrochloride (3.36 g, 48.35 mmol, 3 equiv) at 0 C. The reaction mixture was warmed to room temperature and stirred for 12 h. After completion, the volatiles were removed under reduced pressure and ethyl acetate was added to the residue. The organic layer was washed with saturated NaHCO3solution, dried over sodium sulfate, filtered and the concentrate under reduced pressure. The crude was triturated with n-hexane to afford 3.1 g of (4-chlorophenyl) (pyridin-2-yl) methanone oxime (Yield = 83%). ESI + MS: m/z 233 ([M + Hj).

With the rapid development of chemical substances, we look forward to future research findings about 6318-51-0.

Reference:
Patent; THE BROAD INSTITUTE, INC.; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOLSON, Edward; WAGNER, Florence, Fevrier; WEIWER, Michel; SCOLNICK, Edward; PALMER, Michelle; LEWIS, Michael; PAN, Jennifer, Q.; ZHANG, Yan-Ling; XU, Qihong; (323 pag.)WO2016/100823; (2016); A1;,
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

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

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

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.132521-70-1, name is 6-(4-Methylpiperazin-1-yl)nicotinic acid, molecular formula is C11H15N3O2, molecular weight is 221.26, as common compound, the synthetic route is as follows.Computed Properties of C11H15N3O2

6-(4-methylpiperazin- 1 -yl)nicotinic acid (132 mg,0.6 mmol), tert-butyl 2-amino-4-(pyridin-4-yl) phenylcarbamate (172 mg, 0.6 mmol) and EDCI (346 mg, 1.8 mmol) were added into pyridine (5 ml). The mixture was stirred for overnight at room temperature. When the reaction finished, it was extracted by EA and washed by citric acid, NaHCO3 and saturated brine. Then the organic layer was concentrated to afford compound 2 (300 mg, crude).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,132521-70-1, 6-(4-Methylpiperazin-1-yl)nicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1201676-03-0, 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.1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.03, as common compound, the synthetic route is as follows.

A solution of 4,6-dichloro-2H,3H-pyrrolo[3,4-c]pyridin-l-one (1.0 g, 4.9 mmol, 1 eq.), 2- cyclopropyl-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (2.0 mL, 11 mmol, 2.2 eq.), [1,1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (0.80 g, 1.0 mmol, 0.2 eq.) and potassium carbonate (3.4 g, 25 mmol, 5 eq.) in dioxane-water (10: 1 v/v, 15 mL) was degassed and heated at 80 C for 16 hours. After cooling the mixture, it was diluted with water and extracted with 15% isopropanol in chloroform (3x). The combined organic layers were dried, filtered and concentrated. The product was purified chromatography B to afford the title compound (0.44 g, 42%) as a white solid.

Statistics shows that 1201676-03-0 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem