Tag: M.W:100-200

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.106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.name: 5-Amino-2-(trifluoromethyl)pyridine

EXAMPLE 3 [0186] [CHEMMOL-00538] [0187] Step 1 [0188] 3-Amino-6(trifluoromethyl)pyridine (1.0 g, 6.2 mmol), N-Boc-4-piperidone (1.5 g, 7.4 mmol), Na(AcO)3BH (2.0 g, 9.3 mmol), and AcOH (0.35 mL, 6.2 mmol) were taken up in 1,2-dichloroethane and stirred at 55 C. for 17 hours. The solution was diluted with CH2Cl2 and quenched with 1 N NaOH. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated to furnish a yellow oil. The residue was resubjected to the reaction conditions for 20 hours. After workup, a yellow oil was obtained. The amine product was purified via recrystallization (CH2Cl2/hexanes) to give 1.6 g (75%) of the amine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,106877-33-2, 5-Amino-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2004/10008; (2004); 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. 20260-53-1, name is Nicotinoyl chloride hydrochloride, molecular formula is C6H5Cl2NO, 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. Formula: C6H5Cl2NO

To a mixture of N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (94.8 mg, 0.30 mmol) and isonicotinoyl chloride hydrochloride (56.1 mg, 0.32 mmol) in THF (2.0 mL) at room temperature was added N,N-diisopropylethylamine (0.157 mL, 0.90 mmol). After stirring for 3 hours at room temperature, an additional 21 mg of isonicotinoyl chloride hydrochloride was added and the reaction continued for 17 hours. The reaction was quenched with H2O, then treated with an EtOAc/saturated NaHCO3(aq) solution work-up to give an off-white solid. The solid was recrystallized from EtOAc/hexane to afford a white solid (115 mg, 91%). (0276) 1H NMR (300 MHz, DMSO-d6) delta ppm 2.76-2.95 (m, 2H) 3.52-3.59 (m, 1H) 3.61 (s, 3H) 3.74 (s, 6H) 3.95 (t, J=6.74 Hz, 1H) 4.43 (br. s., 1H) 4.71 (s, 1H) 7.17-7.27 (m, 2H) 7.39-7.56 (m, 2H) 8.19 (s, 0.37H, minor rotamer) 8.42 (s, 0.63H, major rotamer) 8.67-8.74 (m, 2H) 9.44 (br. s., 1H).

With the rapid development of chemical substances, we look forward to future research findings about 20260-53-1.

Reference:
Patent; Allergan, Inc.; Wurster, Julie A.; Malone, Thomas C.; Hull, III, Clarence Eugene; Rao, Sandhya; Yang, Rong; Yee, Richard; (24 pag.)US9296747; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58584-94-4, 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. 58584-94-4, name is 2,6-Dichloro-3-methylpyridine, molecular formula is C6H5Cl2N, 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.

(2d) 2,6-Dichloro-3-methyl-5-nitropyridine [Formula 21]; Anhydrous trifluoromethanesulfonic acid (21.9 ml, 129 mmol) was dropped into a mixture of tetramethyl ammonium nitrate (17.3 g, 127 mmol) and dichloromethane (60 ml) at 0C under nitrogen flow, and the reaction mixture was stirred for 1.5 hours while elevating to room temperature. After a 10: 1.5 mixture (13.7 g) of 2,6-dichloro-3-methylpyridine and 2,4-dichloro-5- methylpyridine in dichloromethane (20 ml) was added and stirred for 30 minutes at room temperature, the reaction mixture was stirred under reflux for 48 hours. The reaction mixture was poured into a saturated sodium bicarbonate solution, and extracted with dichloromethane (200 ml), and after washed with water, dried over magnesium sulfate. The residue obtained by evaporating the solvent was triturated with heptane, thereby yielding the title compound (6.55 g, 31.6 mmol) as a pale brown solid. ¹H NMR (400MHz, DMSO-d6)8 ppm; 2.42(3H, s), 8.70(1H, s).

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 58584-94-4, 2,6-Dichloro-3-methylpyridine.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18614-51-2, name is 4-Amino-2-fluoropyridine, the common compound, a new synthetic route is introduced below. Quality Control of 4-Amino-2-fluoropyridine

In a 10 mL microwave vial, Pd2(dba)3 (21.61 mg, 0.024 mmol), cesium carbonate (77 mg, 0.236 mmol), 2-dicyclohexylphosphino-2?-(N,N-dimethylamino)-biphenyl (DavePhos, 18.58 mg, 0.047 mmol), 4-amino-2-fluoropyridine (8.82 mg, 0.079 mmol), and (R)-3-chloro-10-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[5?,6?:4,5]thieno[3,2-f]quinolin-8-one (S1-12) (25 mg, 0.079 mmol) were dissolved in 0.5 mL of dry t-BuOH. The reaction was placed under vacuum then backfilled with nitrogen. The reaction was heated to 100 C. overnight then cooled, filtered and concentrated to dryness. The residue was redissolved in DMSO and purified by reverse phase HPLC with 95%-5% H2O (containing 0.5% TFA v/v)/acetonitrile to afford compound I-3 (0.004 g, 7.8 mumol, 10.0% yield). MS: m/z 393.6 (M+H), 391.7 (M-H). 1H NMR (400 MHz, DMSO-d6): delta 1.13 (d, 3H), 3.39 (m, 2H), 3.55 (m, 1H), 6.94 (br s, 1H), 7.20 (d, 1H), 7.81 (d, 1H), 7.99 (m, 4H), 9.02 (d, 1H), 10.21 (s, 1H).

The synthetic route of 18614-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Celgene Avilomics Research, Inc.; Alexander, Matthew David; Chuaqui, Claudio; Malona, John; McDonald, Joseph John; Ni, Yike; Niu, Deqiang; Petter, Russell C.; Singh, Juswinder; (164 pag.)US2016/75720; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4,6-Dichloronicotinic acid

To a solution of 4,6-dichloronicotinic acid (250 mg, 1.302 mmol), ethyl 3- aminopropanoate hydrochloride (210 mg, 1.367 mmol) and pyridine (0.263 mL, 3.26mmol) in DCM (5 mL) at 0 C was added phosphoryl trichloride (319 mg, 2.083 mmol). The mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into iced water, extracted with DCM (50 mL), washed with saturated NaHCO3 (aq) and brine. The organic extract was dried over Na2SO4, filtered and concentrated in vacuo. The crude intermediate, ethyl 3-(4,6-dichloronicotinamido)propanoate, was thendissolved in dry THF (5 mL) and put under an atmosphere of nitrogen. The solution obtained was cooled to 0 C. Methylmagnesium bromide (2.60 mL, 7.81 mmol) was added and the mixture was stirred at room temperature for 3h. The reaction mixture was quenched with a saturated solution of NH4C1 (aq), extracted with ethyl acetate, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crudeintermediate 4,6-dichloro-N-(3 -hydroxy-3-methylbutyl)nicotinamide was dissolved in DCM (5 mL) and the mixture was cooled to 0 C. DAST (0.189 mL, 1.432 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was then quenched with a saturated solution of NaHCO3 (aq), extracted with DCM, dried over Na2SO4, filtered and concentrated in vacuo. The cmde product was purified viacolumn chromatography to afford 4,6-dichloro-N-(3-fluoro-3-methylbutyl)nicotinamide(126 mg, 35 % yield). LCMS m/z 279.2 (M+H) ?H NMR (400MHz, CDC13) 8.67 (s,1H), 7.48-7.38 (m, 1H), 6.70-6.50 (m, 1H), 3.74-3.59 (m, 2H), 2.06-1.90 (m, 2H), 1.48 (s,3H), 1.43-1.42 (m, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 73027-79-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUNCIA, John V.; GARDNER, Daniel S.; HYNES, John; MACOR, John E.; MURUGESAN, Natessan; SANTELLA, Joseph B.; WU, Hong; KANTHETI, Durgarao; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; RATNA KUMAR, Sreekantha; SARKUNAM, Kandhasamy; SISTLA, Ramesh Kumar; POLIMERA, Subba Rao; (254 pag.)WO2016/210036; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 791644-48-9, 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 791644-48-9 as follows.

5-Fluoro-lH-pyrazolo [3, 4-b]pyridin-3-amine (5) [00148] To a solution of compound 4 (50 g, 321.7 mmol) in 1-butanol (1 L) was added hydrazine monohydrate (150 mL, 3.2 mol) , and the mixture was refluxed for 4 h. The mixture was cooled to room temperature and concentrated. The precipitate was successively washed on filter with water (2x) and Et2<0 (2x) and dried in vacuo overnight to give compound 5 (44 g, 88percent) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): delta 5.53 (s, 2H); 7.94 (dd, IH); 8.35 (dd, IH); 12.02 (s, IH). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,791644-48-9, its application will become more common. Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/112646; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58757-38-3, 6-Chloronicotinoyl chloride, 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, HPLC of Formula: C6H3Cl2NO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3Cl2NO

Example 23 6-([3-(Cyclopropylmethyl)-2,3,4,5-tetrahydro-1 H-3-benzazepin-7-yl]oxy}-N-methyl-3- pyridinecarboxamide (E23) Step 1: 6-Chloro-N-methyl-3-pyridinecarboxamide; 2M Methylamine in tetrahydrofuran (100 ml, 200 mol) was cooled to 0C and 6- chloronicotinoyl chloride (10.6g, 60 mmol) dissolved in dichloromethane (30 ml) was added dropwise. The solution was stirred to room temperature overnight and concentrated in vacuo. The residue was partitioned between dichloromethane and water, the aqueous phase was extracted with dichloromethane (x3). The combined extracts were washed with water, saturated brine and dried over anhydrous magnesium sulphate. The filtrate was concentrated to a crude solid that was used without further purification. (ES+) m/e 171 [M+H]+.

The synthetic route of 58757-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/97778; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 100704-10-7, 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 100704-10-7, name is (2-Chloropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

SOCI2 (4.2 g, 35.5 mol) was added dropwise to a suspension of the alcohol (5 g, 34.8 mmol) in CH2CI2 (50 mL) at -5 0C with stirring, The mixture was stirred at room temperature overnight, then quenched with water (100 mL), and extracted with CH2CI2 (3 x 100 mL). The organic layers were combined, washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1 /5) and afforded the title compound (5.5 g, near quantitative yield) as an oil.

According to the analysis of related databases, 100704-10-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert George; WALKER, David Winter; WO2010/7374; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89466-16-0, Adding some certain compound to certain chemical reactions, such as: 89466-16-0, name is 6-Bromo-3-methylpyridin-2-amine,molecular formula is C6H7BrN2, 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 89466-16-0.

To a solution of scheme 8-38 compound S1 (1 g, 3.89 mmol) and 6-bromo-3-methylpyridin-2-amine (870 mg, 4.67 mmol) in DCE (10 ml) was added DIPEA (2.56 mL, 15.56 mmol) and EEDQ (1.92 g, 7.78 mmol). The reaction was stirred at 90 oC overnight. The solvent was removed under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate =2: 1) to afford scheme 8-38 compound S2 (710 mg, 43.0% yield) as a white solid. LC/MS (ESI) m/z: 426 (M+H)+.

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. 89466-16-0, 6-Bromo-3-methylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (508 pag.)WO2017/35409; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 69950-65-8, name is Methyl 6-formyl-2-pyridinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 69950-65-8

General procedure: To a solution of 3-bromo-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridine (18, 550 mg, 1.59 mmol) in THF (4 mL) was added n-butyllithium (0.7 mL, 1.91 mmol, 2.6 mol/L solution in hexane) at -78 C. After stirring at -78 C for 0.5 h, a solution of methyl 6-formylpicolinate (527 mg, 3.19 mmol) in THF (4 mL) was added to the mixture at -78 C. The solution was stirred at room temperature for 1 h, and then the reaction was quenched by the addition of saturated aq. ammonium chloride. The mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt = 4:1) to give the title compound 23 as a yellow oil (361 mg, 53%).

With the rapid development of chemical substances, we look forward to future research findings about 69950-65-8.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Saito, Yoshifumi; Watanabe, Hiroyuki; Kondo, Tatsuhiro; Kondo, Atsushi; Kawamura, Naohiro; Tatani, Kazuya; Kohno, Yasushi; Tanaka, Nobuyuki; Seto, Shigeki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4044 – 4050;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem