Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic acid, 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, Recommanded Product: 167837-43-6, blongs to pyridine-derivatives compound. Recommanded Product: 167837-43-6

To a solution OF METHYL- (2-METHYLBENZOFURAN-3-YLMETHYL)-AMINE (176 mg, 1.0 mmol), 3- (6-AMINO-PYRIDIN-3-YL)-ACRYLIC acid (150 mg, 0.91 mmol), HOBt (135 mg, 1.0 mmol) and diisopropylethylamine (0.46 mL, 2.7 mmol) in DMF (10 mL) was added EDC (209 mg, 1. 1 mmol). The yellow solution was stirred overnight at room temperature. The reaction mixture was cooled to 0 C then treated with H20 (40 mL) to form a precipitate. The precipitate was filtered, washed with H20 (20 mL) then with a 10% EtOAc: hexanes solution (10 mL). The solid was dissolved in a 10% MeOH: CH2Cl2 solution (20 mL), cooled to 0 C then treated with 2 mL of a 1.0 M HCl in ET20. After stirring for 10 minutes, the yellow solution was concentrated to dryness then triturated with Et2O (20 mL). The title compound was collected and dried under vacuo to yield the title compound (76.9%) as a mixture of amide rotamers. 1H NMR (300 MHz, DMSO-D6) 8 8. 41-8. 33 (m, 3H), 7.58- 7.02 (m, 6H), 4.93 and 4.74 (2 x s, 2H), 3.05 and 2.82 (2 x s, 3H), 2.53 and 2.48 (2 x s, 3H); MS (ESI) NALE 322 (M+ H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 823221-93-8, 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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, 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.

General procedure: To a solution of halogenopyridine (1.0 eq) in indicated solvent at rt was added hydrazinehydrate (1-10 eq.). Reaction mixture was stirred at the indicated temperature for theindicated time. Solvents were concentrated under vacuum. Water or saline solution was then added Precipitate that formed was filtered off, washed with water and dried under vacuum yielding 2-hydrazinylpyridi ne.

According to the analysis of related databases, 823221-93-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2, 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 64951-08-2 as follows.

Step (d) N-[4-(l-cyclopentyl-6-fluoro-2,4-dioxo-l,4-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)cyclohexyl]imidazo[l,2-a]pyridine-2-carboxamide To a mixture of imidazo[l,2-a]pyridine-2-carboxylic acid (89mg, 0.55mmol), HATU(220mg, 0.55mmol), HOAT (75mg, 0.55mmol) and 3-(4-aminocyclohexyl)-l-cyclopentyl-6-fluoro-pyrido[2,3-d]pyrimidine-2,4(lH,3H)-dione hydrochloride (176mg, 0.46mmol) inN-methylpyrrolidinone (10ml) was added ethyl-di-isopropylamine (0.31ml, 1.81mmol) over a period of 20 seconds. Stirring was continued at ambient temperature for 3 days and the reaction mixture was poured onto water. The obtained solid was filtered, dried on the sinter, dissolved in chloroform and adsorbed onto silica gel. Flash chromatography using a mixture of petrol ether and ethyl acetate yielded the title compound (55mg, 24%) as a colourless solid.1H NMR (300MHz, DMSO-J*): delta 8.77 (IH, d); 8.60 (IH, ddd); 8.40 (IH, s); 8.25 (IH, dd); 7.78 (IH, d); 7.68 (IH, d); 7.38 (IH, dd); 7.00 (IH, dd); 5.80 (IH, p); 4.84 (IH, bt);2.89 (IH, bs); 2.50 – 2.70 (2H, bm); 2.04 – 2.22 (2H, bd); 1.41 – 2.04 (12H, m).APCI-MS m/z: 491 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13466-35-8, 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.13466-35-8, name is 3-Chloro-2-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.54, as common compound, the synthetic route is as follows.

EXAMPLE 1 3-Chloro-5-octyl-2-(4-octyloxyphenyl)pyridine 10.5 ml (203.0 mmol) of bromine are added dropwise at 0 C. to 23.9 g (184.5 mmol) of 3-chloro-2-hydroxypyridine in 240 ml of dimethylformamide, and the mixture is stirred at room temperature for 2 hours. 200 ml of water are subsequently added, and 30 g of sodium sulfite in 100 ml of water are added dropwise. After 15 minutes, the mixture is extracted three times with 200 ml of dichloromethane in each case, the combined organic phases are dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness, giving 36.58 g of 5-bromo-3-chloro-2-hydroxypyridine. STR13 m.p.: 168 C. (decomp.)

The chemical industry reduces the impact on the environment during synthesis 13466-35-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoechst Aktiengesellschaft; US5629428; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884494-35-3 ,Some common heterocyclic compound, 884494-35-3, molecular formula is C5H3ClFNO, 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.

tert-butyl 4-(2-chloroacetamido)piperidine-1-carboxylate (2.02 g, 7.3120 mmol) and 2-chloro-5-fluoropyridin-3-ol (1.08 g, 7.32 mmol) weredissolved in DMF (70 ml). Caesium carbonate (4.88 g, 15 mmol) was added and the mixture heated to 1 oooc for 18 hours. After cooling toroom temperature the mixture was partitioned between ethyl acetateand water and the organic phase washed with water. The organic layerwas then evaporated onto silica and purified by flash column5 chromatography eluting with 20 to 100% ethyl acetate/iso-hexane togive the title compound (2.19 g, 85% yield). 1H NMR (400 MHz, CDCb):o 7.80 (d, J=2.5 Hz, 1 H), 7.23 (dd, J=2.7, 9.0 Hz, 1 H), 4.70 (s, 2H), 4.43- 4.29 (m, 3H), 2.81 (m, 2H), 2.50 – 2.37 (m, 2H), 1.74 (dd, J=1.5, 11.6Hz, 2H), 1.50 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-35-3, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 182275-70-3 , The common heterocyclic compound, 182275-70-3, name is 2-Iodo-6-methoxypyridine, molecular formula is C6H6INO, 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.

tei -Butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2/-/)- carboxylate (Intermediate 7) (395 mg, 1.28 mmol) and Cs2C03 (1.03 g, 3.19 mmol) were added to a solution of 2-iodo-6-methoxypyridine (Intermediate 8) (300 mg, 1.28 mmol) in 1 ,4-dioxane (10 mL) and the resulting mixture was degassed under a nitrogen atmosphere for 20 min. (9,9-Dimethyl-9/-/-xanthene-4,5-diyl)bis(diphenylphosphane) (Xantphos, 36 mg, 0.06 mmol) and palladium(ll) acetate (29 mg, 0.13 mmol) were added and the resulting reaction mixture was stirred at 80 C for 18 h. The solvents were removed in-vacuo and residue was partitioned between H20 (80 mL) and EtOAc (60 mL). The aqueous layer was further extracted with EtOAc (60 mL) and the combined organic layers were dried (Na2S04) and the solvent was removed in-vacuo. The residue was purified by column chromatography (normal phase neutral activated alumina, 10 % to 12 % EtOAc in hexane) to give tert- butyl 6- methoxy-3′,6′-dihydro-2,4′-bipyridine-T(2’/-/)-carboxylate (310 mg, 84 %) as a gum. LCMS (System 3, Method D): m/z 291 (M+H)+ (ESI +ve), at 5.73 min, 202 nm.

The synthetic route of 182275-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEPTARES THERAPEUTICS LIMITED; BROWN, Giles; TEOBALD, Barry; TEHAN, Ben; (77 pag.)WO2019/243851; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 2897-43-0, Adding some certain compound to certain chemical reactions, such as: 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine,molecular formula is C5H3Cl2N3O2, 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 2897-43-0.

Intermediate 3: 2,6-Dichloro-3,4-pyridinediamine; 2,6-dichloro-3-nitro-4-pyridinamine (881 mg, 4.24mmol) was taken up in ethanol (15ml) and tin(ll) chloride (3212mg, 16.94mmol) was added portion wise over 5min. The resulting pale yellow solution was allowed to stir at 50C under N2 for 3h, LCMS showed approx 60% conversion, the reaction was left for a further 3h, LCMS showed almost complete conversion. The reaction was allowed to cool to room temperature and was partitioned between NaHC03 (aq) (50ml) and EtOAc (50ml). The organic layer was dried using a hydrophobic frit, concentrated and dried in vacuo overnight to give the title compound as a yellow solid (734mg). LCMS (Method B): Rt = 0.57min, MH+ = 178

According to the analysis of related databases, 2897-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); 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. 52605-96-6, name is 2-Chloro-3-methoxypyridine, the common compound, a new synthetic route is introduced below. Product Details of 52605-96-6

The 2-chloro-3-methoxypyridine (2) (13 g, 90.6 mmol), from Step I, was stirred with 3-equivalents of sodium methoxide (14.7 g, 271.8 mmol) in dimethylformamide (100 mL) at 100 C. until completion of the reaction. The reaction mixture was then quenched with water and extracted with dichloromethane. The combined extracts were washed with water, concentrated and distilled (74 C.; 5 mm Hg) to give the product, 2,3-dimethoxypyridine (3), as a clear oil (7 g; 29% yield for two steps).1H NMR (300 MHz, CDCl3) delta 7.65 (dd, 1 H, J1=5.1 Hz, J2=1.5 Hz), 6.96(dd, 1 H, J1=7.5 Hz, J2=1.5 Hz), 6.76(dd, 1 H, J1=5.1 Hz, J2=7.7 Hz), 3.95 (s, 3 H), 3.80 (s, 3 H).

The synthetic route of 52605-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BioNumerik Pharmaceuticals, Inc.; US2008/261919; (2008); 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. 178876-83-0, name is Methyl 6-amino-3-bromopicolinate, the common compound, a new synthetic route is introduced below. name: Methyl 6-amino-3-bromopicolinate

To a solution of 6-amino-3-bromo-pyridine-2-carboxylic acid methyl ester (3 g, 12.99 mmol) and trimethyl boroxine (1.8 mL, 2.99 mmol) in 1,4 dioxane (30 mL) was added K2CO3 (3.5 g, 25.97 mmol) under an argon atmosphere. To this was added PdCl2 (dppf) 2.CH2Cl2 (530 mg, 0.65 mmol) and stirred at 115C for 4 h. The reaction mixture was cooled to room temperature and water was added to residue. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (1.9 g, 88%).MS ESI (m/e): 166.8 [(M+H)+].1H NMR (DMSO, 400 MHz): <5 (ppm) = 7.31(d, J= 8.4 Hz, 1H), 6.53 (d, J= 8.36 Hz, 1H), 5.99 (s, 2H), 3.77 ( s, 3H), 2.21 (s, 3H). The synthetic route of 178876-83-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/92272; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 108118-69-0, 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. 108118-69-0, name is 2,6-Difluoropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 4-(tert~butoxycarbonyl-methyl-amino)-benzoic acid (70 mg, 0.28 mmol) in CHiCi2 (2 mL) was added l-chloro-N,N-2-trimethylpropenylamine (98 muL, 0.74 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6~difluoro-rhoyridin-3-ylamine (30 mg, 0.23 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150 0C for 10 min, after which the resulting mixture was filtered, concentrated and purified by silica gel flash chromatography (0 to 100% EtOAc in hexanes) to afford [4-(5-fluoro-oxazolo[5s4-6]pyridine-2- yl)-phenyl]-methyl-amine (50 mg, 0.21 mmol, 89%). ES MS (M+H+) – 244; Eta NMR (300 MHz, DMSO-d6): delta 8.24 (t, J – 7.7 Hz, 1 H); 7.89 (d, J = 8.4 Hz, 2 H); 7.18 (d, J = 8.4 Hz, 1 H); 6.68 (d, J = 8.5 Hz, 3 H); 2.76 (s, 3 H); HRMS m/z 244.0883 (C13H10FN3O + H+ requires 244.0881).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108118-69-0, 2,6-Difluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/155017; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem