Day: March 24, 2022

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.184416-83-9, name is 2,3-Dichloropyridin-4-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4Cl2N2

A mixture of tert-butyl ((l S)-l’-(3-iodo-l-(tetrahydro-2H-pyran-2-yl)-lH- pyrazolo[3,4-b]pyrazin-6-yl)-l,3-dihydrospiro[indene-2,4′-piperidin]-l-yl)carbamate (350.0 mg, 555.0 pmol, from Intermediate J), 2,3-dichloropyridin-4-amine (135.0 mg, 832.0 pmol, CAS 184416-83-9), XantPhos-Pd-G4 (47.6 mg, 55.4 pmol) and Cs2C03 (270.0 mg, 832.0 pmol) in PhMe (10 mL) was stirred at 100 C for 12 hours. The reaction mixture was concentrated and purified by silica gel column (EtOAc in petroleum ether = 0-30%) to give tert-butyl N-[(3S)-l’-{3-[(2,3-dichloropyridin-4-yl)amino]-l-(oxan-2-yl)-lH-pyrazolo[3,4- b]pyrazin-6-yl}-l,3-dihydrospiro[indene-2,4′-piperidin]-3-yl]carbamate (200.0 mg, 54% yield) as a yellow solid. LCMS m/z [M+H]+ = 665.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184416-83-9, 2,3-Dichloropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14916-65-5, 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. 14916-65-5, name is 6-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 6-nitro-pyridin-3-ylamine (50 mg, 0.33 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 25 mg, 0.66 mmol), and the mixture was stirred at r.t for 30 min. Then 5-bromo-2-methoxy-benzenesulfonyl chloride (86 mg, 0.3 mmol) was added and the mixture was stirred at 50 C overnight. TLC showed that the reaction was complete. The resultant was concentrated in vacuum to remove DMF. The residue was diluted with DCM (30 mL) and the mixture was washed with IN HC1 (30 mL x3) .The organic layer dried over Na2S04 and concentrated to dryness in vacuum. The residue was purified by silica gel column (PE/EtOAc, 1/1) to give 30 mg (yield: 26%) of 5-bromo-2-methoxy-N-(6-nitro-pyridin-3-yl)- benzenesulfonamide as a brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14916-65-5, 6-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; DAHL, Russell; COSFORD, Nicholas, D.P.; MILLAN, Jose, Luis; WO2013/126608; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 97966-00-2, 5-Bromo-2,3-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, COA of Formula: C5H2BrCl2N, blongs to pyridine-derivatives compound. COA of Formula: C5H2BrCl2N

To a solution of 5-bromo-2,3-dichloropyridine (29) (702 mg, 3.09 mmol) in THF (7 ml) was dropwise added isopropylmagnesium chloride lithium chloride complex (3.09 ml, 4.02 mmol) at 0 C. for 10 min. Then N-methoxy-N-methylacetamide (658 mul, 6.19 mmol) in THF (2 ml) was dropwise added to the reaction mixture at the same temperature and stirred at for 2 hrs. Then the reaction mixture was quenched with aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting product was chromatographed on silica gel eluting with a gradient of hexane/ethyl acetate (5-15%) to afford 232 mg of the desired product (30) in 40% yield as a white solid. 1H-NMR (DMSO-d6) delta: 8.91 (1H, s), 8.55 (1H, s), 2.65 (3H, s).

The synthetic route of 97966-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; Kurose, Noriyuki; Iso, Yasuyoshi; Yamaguchi, Naoko; Shao, Bin; Tafesse, Laykea; Zhou, Xiaoming; Yu, Jianming; US9156830; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 23056-47-5, Adding some certain compound to certain chemical reactions, such as: 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine,molecular formula is C6H5BrN2O2, 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 23056-47-5.

A mixture of NH4C1 (14.9 mmol) and iron powder (18.4 mmol) in H20 (5 mE) was stirred at 90 C. 2-bromo-4- methyl-5-nitropyridine (2.3 mmol) was added in portions. The mixture was stirred at 90 C. for 1 h and 15 mm. The reaction was stopped and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated to yield the desired product.

According to the analysis of related databases, 23056-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 109613-97-0, 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. 109613-97-0, name is 2-Bromo-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

To an ice-cold solution of 2-bromo-4-methoxypyridin-3-amine (Intermediate 38), (2.74 g) in pyridine (102 mL) was added ethyl chloroformate (1.91 mL) dropwise and then stirred at rt for 45 min. The reaction mixture was cooled in an ice-bath and more ethyl chloroformate (9 mL) added and the mixture left to stir overnight at rt. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over MgSO4, filtered and evaporated under vacuum to give a solid. Product was observed in the aqueous layer by LC-MS, so this was re-extracted with EtOAc (3*) and evaporated under vacuum to give a solid which was combined with the previous solid, dissolved in DCM and purified by column chromatography (normal phase, 50 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 10-70% EtOAc in n-hexane) to give the desired product (2.35 g). LCMS: m/z 275.43 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.32 (t, J=7.1 Hz, 3H) 3.93 (s, 3H) 4.24 (q, J=7.1 Hz, 2H) 6.06 (br. s., 1H) 6.86 (d, J=5.6 Hz, 1H) 8.19 (d, J=5.6 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109613-97-0, its application will become more common.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60010-03-9, 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, 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.

2,6-Dichloro-4-methyl-3-nitropyridine (Step 31.1;1.17 g, 5.68 mmol) was added at rtto a 2M solution of methylamine in THF and alowed to stir for 30 mm. The reaction mixture was then diluted with EtOAc/water, extracted twice with EtOAc and the combined organic extracts were washed with brine, dried (Na2504) and concentrated. The crude product was purified by flash chromatography (ISCO combi flash; EtOAc/hexanes: 1:4, 5i02) to afford the title compound as a yellow solid. tR: 1.08 mm (LC-MS 2); ESl-MS: 202.0 [M+H]1H NMR (400 MHz, DMSO-d6) 0 ppm 2.39 (5, 3 H) 2.90 (d, J=4.65 Hz, 3 H) 6.73 (5, 1 H) 7.95 (d, J=3.91 Hz, 1 H).

According to the analysis of related databases, 60010-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BOLD, Guido; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191894; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1321612-85-4, 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. 1321612-85-4, name is 3-Fluoro-5-iodopyridin-2-amine, molecular formula is C5H4FIN2, 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.

In a 50-mL round-bottomed flask, the solution of 4-bromobenzenethiol (1.0 g, 5.3 mmol) and 3-fluoro-5-iodo-2-pyridinamine (0.63 g , 2.7 mmol) in DMSO (10 mL) was degassed by purging with argon gas at room temperature for 10 min. K2C03 (2.18 g, 15.9 mmol) and Cul (0.05 g, 0.26 mmol) were added sequentially to the above reaction mixture at room temperature under argon atmosphere. The reaction mixture was heated overnight at 100 C under argon atmosphere. The reaction mixture was cooled to room temperature and filtered through a pad of Celite (diatomaceous earth). The filtrate was diluted with cold water (50 mL) and ethyl acetate (100 mL). The EtOAc layer was separated, washed with water, brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel (100 to 200 mesh) column chromatography (elution 30% EtOAc-hexanes) to give 5-((4-bromophenyl)sulfanyl)-3-fluoro-2-pyridinamine (400 mg) as a white solid.

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 1321612-85-4, 3-Fluoro-5-iodopyridin-2-amine.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); 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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile, the common compound, a new synthetic route is introduced below. Formula: C6H3ClN2

[Referential Example 114]; 4-Methylthiopyridine-2-carbonitrile; Sodium thiomethoxide (1.01 g) was added to 4-chloropyridine-2-carbonitrile (2.00 g) obtained from Referential Example 113 in N,N-dimethylformamide (20 mL) at 0C, followed by stirring for 2 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane – ethyl acetate), to thereby give the title compound as a solid (1.96 g, 90%).1H-NMR(400MHz,CDCl3)delta: 2.53(3H,s), 7.26-7.27(1H,m), 7.45-7.46(1H,m), 8.45-8.46(1H,m). MS(EI)m/z: 150(M+) .

The synthetic route of 19235-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1591443; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1227502-35-3, 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. 1227502-35-3, name is 5-Bromo-3-(hydroxymethyl)pyridin-2(1H)-one, molecular formula is C6H6BrNO2, 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.

Step 3: [0901] To a suspension of 5-bromo-3-(hydroxymethyl)pyridin-2(1H)-one 62 (350 mg, 1.72 mmol), Et3N (0.71 mL, 5.16 mmol) and CH2Cl2 (15 mL) was slowly added methanesulfonyl chloride (0.27 mL, 3.43 mmol) at 0 C. under nitrogen. The reaction mixture was allowed to warm to room temperature for 17 h and then water was added. The layers were separated and the aqueous was extracted with CH2Cl2. The organic phase was dried over sodium sulfate and filtered. The solvent was removed and the residue was purified by silica gel chromatography (eluting with 0 to 30% ethyl acetate in hexanes) to provide compound 63 (75 mg, 15%).

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 1227502-35-3, 5-Bromo-3-(hydroxymethyl)pyridin-2(1H)-one.

Reference:
Patent; RVX Therapeutics Inc.; Liu, Shuang; Duffy, Bryan Cordell; Quinn, John Frederick; Jiang, May Xiaowu; Wang, Ruifang; Martin, Gregory Scott; Zhao, He; Molino, Bruce Francis; Young, Peter Ronald; US2014/179648; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153034-88-9, Adding some certain compound to certain chemical reactions, such as: 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine,molecular formula is C6H5ClIN, 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 153034-88-9.

A mixture of 2-chloro-4-iodo-3-methylpyridine (250 mg, 986 mumol) (AstaTech, catNo.22441) and boric acid, trimethyl ester (224 muL, 1.97 mmol) in tetrahydrofuran (5.0 mL) was added 2.5 M n-butyllithium in hexanes (789 muL, 1.97 mmol) dropwise at -78 C. The reaction mixture was allowed to warm up to r.t. after 90 min and stirred for another 30 min. The resulting mixture was concentrated and acetonitrile (5 mL) was added. The resulting suspension was filtered through celite then concentrated to give the desired product. LCMS calculated for C6H8BClNO2 (M+H)+: m/z=172.2; found 172.2

According to the analysis of related databases, 153034-88-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Li, Zhenwu; Wu, Liangxing; Yao, Wenqing; (48 pag.)US2017/320875; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem