Tag: M.W:100-200

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. 5632-81-5, name is 2-Chloropyridine-3,5-diamine, 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. category: pyridine-derivatives

80 ml of ethanol are placed in a 250-ml one-necked round-bottomed flask equipped with a calcium chloride guard tube, followed by addition, with stirring, of 4.11 g (18.1 mmol) of 2-(propan-2-yloxy)pyrazolo[l,5-a]pyridin-3-amine hydrochloride. 1.18 g (8.21 mmol) of 2-chloropyridine-3,5-diamine and 5.0 ml (29 mol) of N-ethyl-N-(propan-2-yl)propan-2-amine are added to this solution.The solution is then stirred at room temperature for 4 days. The black precipitate formed is isolated by filtration, washed with water and dried in a desiccator under vacuum at 30C in the presence of a desiccant, to constant weight. The compound is thus obtained in the form of a black powder.

With the rapid development of chemical substances, we look forward to future research findings about 5632-81-5.

Reference:
Patent; L’OREAL; FADLI, Aziz; BLAIS, Stephane; (70 pag.)WO2016/97198; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 70298-88-3, 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 70298-88-3 as follows.

To a solution of 2.67 g (15.0 mmol, 1 eq.) of pivalamide IV and 6.8 mL (45.0 mmol, 3 eq.) of TMEDA in 120 mL of dry diethylether, cooled to -78C, were added 18.0 mL (45.0 mmol, 3 eq., 2.5 M in hexane) of BuLi. After 15 minutes, the solution was brought back to -24C and stirred 2 hours. Then, the mixture was cooled down to – 78C before addition of 4.0 mL (33.0 mmol, 2.2 eq) of p-anisaldehyde in 60 mL of THF. The reaction was brought back to 0C and stirred 2 hours before being stirred at room temperature over night. Then, 120 mL of water were added. The aqueous layer was extracted with 2 x 80 mL of dichloromethane. The organic phase was dried, filtered and concentrated. The crude mixture was purified over silicagel. The obtained white solid (estimation 9 mmol of XII) was dissolved in 90 mL of DCM. Then, 7.74 g (89.0 mmol, 10 eq.) of activated Mn02 were added and the reaction was refluxed 20 hours. The reaction was brought back to room temperature and 7.74 g (89.0 mmol, 10 eq.) of activated Mn02 were added again. After 20 hours to reflux, the mixture was filtered on celite and the solvent was evaporated. The crude mixture was dissolved in 180 mL of 3 M aqueous HCI were added and refluxed 16 hours. The reaction was cooled down to 0C and 50 mL of aqueous ammonia were added. The aqueous layer was extracted with 3 x 90 mL of DCM. The organic phase was dried, filtered and concentrated. Purification over silica gel afforded 1.65 g (7.2 mmol, 48%) of XIII as a yellow solid. The yield varied from 38% to 48%. Rf=0.15 (PE/EtOAc 1 :2). 1H NMR (300 MHz): delta = 8.26 (s, 1 H), 7.94 (d, J = 5.1 Hz, 1 H), 7.72 (m, 2 H), 7.22 (m, 1 H), 6.96 (d, J = 5.1 Hz, 2 H), 5.58 (s, 2 H), 3.88 (s, 3 H) ppm. 13C NMR (75 MHz): delta = 196.5, 163.4, 144.0, 141.1 , 137.1 , 132.2, 130.6, 124.7, 123.4, 1 13.8, 55.6 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,70298-88-3, its application will become more common.

Reference:
Patent; LYTIX BIOPHARMA AS; STENSEN, Wenche; SCHEVENELS, Florian; MARKO, Istvan, E.; SVENDSEN, John, Sigurd, Mj°en; WO2014/198848; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13534-98-0, 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 13534-98-0, name is 4-Amino-3-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 3-Prop-1-ynyl-pyridin-4-ylamine (LXXIII). To a solution of LXXII (1.5 g, 8.67 mmol) in N,N-dimethyl formamide (20 mL) was added solid sodium acetate (2.1 g, 0.02106 mol). The resulting mixture was degassed for 10 min and then [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.31 g, 0.430 mmol), followed by tributyl(prop-1-yn-1-yl)stannane (3.7g, 11.3 mmol), were added. The reaction mixture 25 was heated at 100 C in a sealed tube for 12 h, before being allowed to cool to room temperature. The reaction mixture was poured in to water and the mixture was extracted 157 of 363 {//– DRAFT –//4069/3020WO/00228726/v2} 4069.3020 WO with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The crude product mixture was purified by column chromatography on (100-200 mesh) silica, using 3% methanol in dichloromethane as the eluant to afford LXXIII (1 g, 87%) as a semi solid.1H NMR (400 MHz, CDCl3) delta 8.29 5 (s, 1H), 8.08 (d, 2H, J= 5.7 Hz), 6.50 (d, 2H, J= 5.6 Hz), 4.61 (brs, 2H), 2.11 (s, 3H); MS (ESI, positive mode) m/z 133 (MH+).

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 13534-98-0, 4-Amino-3-bromopyridine.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; CULLEN, Matthew; HAUCK, Sheila; GENG, Bolin; FOLEY, Megan; BASTOS, Cecilia, M.; MUNOZ, Benito; HAEBERLEIN, Markus; WO2015/73528; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53014-84-9, 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.53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, molecular weight is 121.1366, as common compound, the synthetic route is as follows.

154. (+)-2- 3,4-trans)-4-methyl-l-g6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- f] ri,2,41triazin-4(3H)-one [1113] To a stirred solution of (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (150 mg, 0.49 mmol) in MeOH (10 mL) was added 6-methylnicotinaldehyde (71 mg, 0.59 mmol) at room temperature and stirred for 2 h under argon atmosphere. To the resulting solution was added NaCNBH3 (93 mg, 1.48 mmol) and stirring was continued for another 8 h at room temperature. The volatiles were evaporated under reduced pressure. The residue was diluted with water and extracted with CH2CI2 (2 x 20 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-((6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5, 1 -f [ 1 ,2,4]triazin- 4(3H)-one (43 mg, 21%) as an off-white solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.38 (s, 1H), 7.67 (s, 1H), 7.58 (d, 1H), 7.21 (d, 1H), 3.97-3.91 (m, 2H), 3.64-3.59 (m, 2H), 3.52-3.49 (m, 1H), 2.94-2.92 (m, 1H), 2.87-2.84 (m, 2H), 2.79-2.71 (m, 2H), 2.67-2.61 (m, 2H), 2.42 (s, 3H), 2.24-2.21 (m, 1H), 1.87-1.82 (m, 4H), 1.09 (d, 3H); Mass (ESI): 409.3 [M++l]; LC-MS: 96.82%; 409.4 (M++l); (column; Eclipse XDB C-18, (150×4.6 mm, 5.0mu); RT 5.58 min. 0.05% TFA (Aq): ACN; 1.0 ml/min); UPLC (purity): 98.45%; (column; Acquity UPLC HSS-T3, 100×2.1 mm, 1.8mu; RT 2.83 min. 0.025% TFA (Aq): ACN; 0.30 ml/min; Chiral HPLC: 99.61%, R,= 9.69 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) 0.1% DEA in n-Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D20: + 18.96 (c = 0.25, DCM). TLC: 5% MeOH/DCM (Rf: 0.3).

The chemical industry reduces the impact on the environment during synthesis 53014-84-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67515-76-8, 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. 67515-76-8, name is Methyl 5-aminopicolinate, molecular formula is C7H8N2O2, 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 62 Preparation of methyl 5-fluoropicolinate STR225 The methyl 5-aminopicolinate (2.2 g) is dissolved in 5.5 ml 48% fluoroboric acid and 20 ml 95% ethanol. This mixture is cooled, with stirring, to -3 C. and then 1.81 g n-butyl nitrite added dropwise. After a further one-half hour at -3 C., 0.5 ml n-butyl nitrite is added slowly and stirring continued for one-half hour at 0 C. After adding 20 ml ether carefully, the mixture is rapidly filtered, and the solid washed twice with cold hexane. The solid is suspended in 100 ml heptane, and the suspension slowly heated with stirring. At about 60 C., a vigorous exothermic reaction occurs. Heating is then continued to 80 C. A red oil separates on the sides of the flask. The heptane solution is filtered, and the filtrate concentrated to give the desired product. The red oil is dissolved in water, excess sodium bicarbonate solution added, and the solution extracted with ethyl acetate. The ethyl acetate extract is washed with saturated brine, dried and concentrated. The residue is chromatographed on silica gel and the product, methyl 5-fluoropicolinate, eluted with 1:1-ether:hexane. This material is used directly for the preparation of the picolinic acid.

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 67515-76-8, Methyl 5-aminopicolinate.

Reference:
Patent; American Cyanamid Company; US4638068; (1987); A;,
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. 1104455-41-5, name is Methyl 4-chloro-5-methylpicolinate. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

To a stirred solution of methyl 4-chloro-5-methylpicolinate (220 mg, 1.2 mmol) in DMSO (10 mL) purged and maintained under an inert atmosphere of N2, was added Cu504.5H20 (15 mg, 0.06 mmol.), KOH (336 mg, 6 mmol) and a solution of 1,2-ethanedithiol (226 mg, 2.4 mmol) in water (1 mL). The resulting solution was heated to 90 oC overnight, cooled to 25 oC and concentrated to afford the crude title compound. MS (ES) m/z 170 (M+H).

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, 1104455-41-5, Methyl 4-chloro-5-methylpicolinate.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; HUDSON, Ryan; BEAUSOLEIL, Anne-Marie; (616 pag.)WO2018/89261; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1003-68-5, 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 1003-68-5 as follows.

A mixture of Cul (0.19 g, 1 mmol), Cs2C03(6.85 g, 20 mmol) and ethyl 2-oxocyclohexanecarboxylate (0.34 g, 2 mmol) in DMSO (10 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 5-methylpyridone (1.09 g, 10 mmol) and 4-(2-fluoro-4-iodobenzyl) morpholine (3.21 g, 10 mmol) in DMSO (12 mL) via syringe. The reaction mixture was heated at 100 C overnight, cooled to rt and filtered. The filtrate diluted with H20 (50 mL) was extracted with CH2C12(50 mL x 3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE / EtOAc (V / V) = 10 : 1) to give the title compound as a white solid (0.70 g, 23%). The compound was characterized by the following spectroscopic data:MS (ESI, pos.ion) m/z: 303.2 (M+l);-NMR (400 MHz, CDC13): delta 2.06 (s, 3 H), 3.16-3.32 (m, 4 H), 3.86-3.97 (m, 4 H), 4.44 (s, 2 H), 6.47 (d, 1 H, J = 9.6 Hz), 7.39-7.44 (m, 2 H), 7.48 (s, 1 H), 7.52-7.55 (m, 1 H), 7.99 (t, 1 H, J= 8.2 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; WANG, Xiaojun; LIN, Runfeng; CAO, Shengtian; WANG, Zhaohe; LI, Jing; WO2014/12360; (2014); 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. 13362-78-2, name is (E)-1,2-Di(pyridin-4-yl)ethene, molecular formula is C12H10N2, 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: C12H10N2

General procedure: Equimolar amounts of 1,10-diiodoperfluorodecane (1e) and dipyridyl 2a or its ethylene analogue 2b were dissolved in a vial containing chloroform at room temperature and in a vial. The open vial was closed in a cylindrical bottle containing paraffin oil. Chloroform was allowed to diffuse at room temperature and after two days 1e·2a,b were isolated as white crystals, washed with n-pentane, and characterized.

With the rapid development of chemical substances, we look forward to future research findings about 13362-78-2.

Reference:
Article; Catalano, Luca; Metrangolo, Pierangelo; Pilati, Tullio; Resnati, Giuseppe; Terraneo, Giancarlo; Ursini, Maurizio; Journal of Fluorine Chemistry; vol. 196; (2017); p. 32 – 36;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19437-26-4, 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 19437-26-4 as follows.

General procedure: Two drops of glacial acetic acid as a catalyst were added to themixtures of thiosemicarbazides (0.5 mmol) and di(2-pyridyl) ketone,2-pyridinecarboxaldehyde, 2-quinolinecarboxaldehyde, 8-hydroxy-2-quinolinecarboxaldehyde or 2-quinoxalinecarbaldehyde (0.5 mmol) in ethanol (5 ml). The glasstubes were sealed and placed into a microwave reactor at 83 C for20 min (the reactor power did not exceed 50W). The final productswere crystallized from dry methanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19437-26-4, its application will become more common.

Reference:
Article; Mrozek-Wilczkiewicz, Anna; Malarz, Katarzyna; Rejmund, Marta; Polanski, Jaroslaw; Musiol, Robert; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 180 – 194;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 98400-69-2, 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. 98400-69-2, name is 4-(Boc-Amino)pyridine. A new synthetic method of this compound is introduced below.

8.1 1,1-Dimethylethyl (3,5-dibromopyrid-4-yl)carbamate A mixture of 1,1-dimethylethyl 4-pyridinecarbamate (11.0 g; 57.0 mmol) and N-bromosuccinimide (25.6 g; 142.0 mmol) in acetonitrile (50 ml) is heated for 12 hours at 55° C. The reaction mixture is concentrated under reduced pressure. The residue obtained is taken up in ether (400 ml), washed with saturated aqueous potassium bicarbonate solution (2*200 ml), dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue is chromatographed on a column of silica, eluding with an ethyl acetate/cylohexane gradient of from 0 to 10percent ethyl acetate. 8.2 g of 1,1-dimethylethyl (3,5-dibromopyrid-4-yl)carbamate are isolated in the form of a white solid. Yield (percent)=41

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98400-69-2, its application will become more common.

Reference:
Patent; Altenburger, Jean-Michel; Cremer, Gerard; Lassalle, Gilbert; Matrougui, Mostafa; US2003/207920; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem