Month: April 2022

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. 909717-95-9, name is Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C11H12N2O3, 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. Application In Synthesis of Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate

A mixture of the product from step 2 (500 mg, 126 rnmol) in 40% HBr (20 mL) was stirred at 120C for 16 hours. After cooling to RI, the mixture was concentrated in vacuo to give a residue, which was neutralized with saturated NaHCO3 aqueous solution to pH 7, extracted with the mixed solvent (DCM: iPropanol = 4: 1) (500 mL x 3). The organic layer was combined, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified bysilica chromatography (10% methanol in DCM) to give the title compound (290.0 mg) as yellow oil. LRMS mlz (M+H) 135,1 found, 135.1 required.

With the rapid development of chemical substances, we look forward to future research findings about 909717-95-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); 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. 178421-21-1, name is Ethyl 6-chloro-5-methylpicolinate, the common compound, a new synthetic route is introduced below. Recommanded Product: 178421-21-1

Stage 1: (6-chloro-5-methylpyridin-2-yl)methanol 0.40 g of sodium borohydride (10.5 mmol) is added in portions to a solution of 1.20 g of 6-chloro-5-methylpyridine-2-carboxylic acid ethyl ester (6.00 mmol) and 10 ml of ethanol maintained at room temperature. The mixture is stirred for 4 hours and then the mixture is poured into an aqueous solution of sodium chloride and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform). 0.69 g of a colorless oil is recovered. Yield: 73% 1 H NMR (CDCl3) delta: 2.37 (s, 3H); 4.70 (s, 2H); 2.94 (s; broad); 7.17 (d, 1H); 7.55 (d, 1H)

The synthetic route of 178421-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pierre Fabre Medicament; US6020345; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56673-34-8 ,Some common heterocyclic compound, 56673-34-8, molecular formula is C5H4BrNS, 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.

5-Bromo-2-(cyclopropylmethylthio)pyridine To a solution of 5-bromopyridine-2-thiol (3.9 g) in THF (100 mL) was added NaH (1.24 g) at 0 C. and the mixture was stirred at 0 C. for 0.5 h. Then (bromomethyl)cyclopropane (2.79 g) was added. The mixture was allowed to warm to r.t. and stirred for 6 hours. The mixture was poured into ice water (200 mL) and extracted with EA (100 mL*3). The combined organic phases were washed with brine (50 mL) and then dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by SGC (eluent: PE) to provide the subtitle compound. MS ESI+: m/z=244 [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. 56673-34-8, 3-Bromo-6-mercaptopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BOSSART, Martin; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; KLABUNDE, Thomas; MAIER, Thomas; STENGELIN, Siegfried; US2014/99333; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 722550-01-8, 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.722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine, molecular formula is C9H13N3, molecular weight is 163.22, as common compound, the synthetic route is as follows.

To a stirred solution of (4,S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-l,4- methanopyrido[2,3-£][l,4]diazepine (300 mg, 1.189 mmol in THF (30 mL) ) were added triethylamine (0.829 mL, 5.94 mmol) and triphosgene (353 mg, 1.189 mmol) under nitrogen, stirred at RT for 1 h. To this 4-(pyrrolidin-l-yl)pyridin-2-amine (388 mg, 2.378 mmol) was added and stirred at 70 C for 16 h. (TLC eluent: 10% MeOH in DCM, 1^:0.4, UV active). The reaction mixture was cooled to rt, partitioned between water and ethyl acetate (3X30 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SC”4, filtered and filtrate was evaporated to get crude compound. The crude compound was purified by flash column chromatography (using neutral alumina and eluted at 20% EtOAc in pet ether) to afford the desired product (4,S)-7-(2-methylpyridin-4- yl)-N-(4-(pyrrolidin-l-yl)pyridin-2-yl)-3,4-dihydro-l,4-methanopyrido[2,3- £][l,4]diazepine-5(2H)-carboxamide (251 mg, 0.561 mmol, 47.2 % yield) as an off white solid. LCMS (m/z): 442.3 [M+H]+, Rt = 4.78 min.1H NMR (400 MHz, CDC13): delta 13.27 (s, 1 H), 8.60 (d, J = 5.3 Hz, 1 H), 8.28 (s, 1 H), 8.00 (d, J = 5.9 Hz, 1 H), 7.72 (dd, J = 5.5, 1.8 Hz, 1 H), 7.59 (d, J = 7.9 Hz, 1 H), 7.50 – 7.38 (m, 2 H), 6.19 (dd, J = 5.9, 2.3 Hz, 1 H), 5.70 (dd, J = 6.0, 3.2 Hz, 1 H), 3.39 (q, J = 6.2, 4.8 Hz, 3 H), 3.26 (s, 1 H), 3.27 – 3.12 (m, 3 H), 3.00 (dd, J = 12.0, 3.3 Hz, 1 H), 2.74 (s, 3 H), 2.32 (dddd, J = 14.0, 10.0, 6.2, 4.2 Hz, 1 H), 2.15 – 1.97 (m, 5 H).

Statistics shows that 722550-01-8 is playing an increasingly important role. we look forward to future research findings about 4-(Pyrrolidin-1-yl)pyridin-2-amine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); 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.135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.Quality Control of 6-(Chloromethyl)-2-cyanopyridine

Reference Example 149-1 tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-3-methyl-2-oxobutyl]-5-methoxyphenyl}carbamate Under an argon atmosphere, to a solution of tert-butyl [5-methoxy-2-(3-methyl-2-oxobutyl)phenyl]carbamate (337 mg) in N,N-dimethylformamide (4 mL) was added sodium hydride (50-72% in oil, 56 mg) under ice-cooling, and the mixture was stirred for 30 minutes. 6-(Chloromethyl)pyridine-2-carbonitrile (167 mg) was added thereto, followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (271 mg). 1H-NMR (CDCl3) delta ppm: 0.91 (3H, d, J=6.5 Hz), 1.07 (3H, d, J=7.3 Hz), 1.57 (9H, s), 2.56-2.72 (1H, m), 3.18 (1H, dd, J=8.2, 15.9 Hz), 3.61 (1H, dd, J=6.8, 15.9 Hz), 3.77 (3H, s), 4.65-4.74 (1H, m), 6.58 (1H, dd, J=2.8, 8.7 Hz), 6.92 (1H, d, J=8.7 Hz), 7.22-7.29 (1H, m), 7.35 (1H, d, J=2.8 Hz), 7.46-7.60 (2H, m), 7.65 (1H, t, J=7.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 29241-65-4, 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. 29241-65-4, name is 5-Bromo-2-chloronicotinic acid, molecular formula is C6H3BrClNO2, 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.

Compounds are represented in generic form, with sub stituents as noted in compound descriptions elsewhere herein. A more specific example is set forth below. In one aspect, ethers of type 6.7 can be prepared beginning with the commercially available 5-bromo-2-chloronicotinic acid, which is converted to the corresponding ester by reaction with methanol in the presence of an acid such as hydrochloric acid to yield compound 6.2. Alkylation to provide compound 6.3 is accomplished by use of a Suzuki cross coupling reaction using potassium allyltrifluoroborate in the presence of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II). Reaction with 4-methoxybenzylamine affords compound 6.4. A cross-coupling reaction between compound 6.4 and benzyl alcohol in the presence of CuI, Cs2CO3, and a diamine ligand yields the aryl ether, compound 6.5. The p-methoxybenzyl protecting group is removed using cerium(IV) ammonium nitrate (CAN), followed by reduction of the carbonyl using lithium aluminum hydride. The amide, compound 6.7, is formed by reaction of the 3-(benzyloxy)-5,6,7,8-tetrahydro-1,6-naphthyridine, formed in the previous step, with benzoyl chloride.

According to the analysis of related databases, 29241-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Dawson, Eric S.; US2012/178776; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1256811-02-5, 1-(5-Bromo-2-methoxypyridin-3-yl)ethanone, 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: C8H8BrNO2, blongs to pyridine-derivatives compound. HPLC of Formula: C8H8BrNO2

[0118] 1-(5-Bromo-2-methoxy-pyridin-3-yl)ethanone (XXXVI) (200 mg, 1.404mmol) was dissolved in N,N-dimethylformamidedimethyl acetal (DMFDMA) (1.7 ml, 14.03 mmol), and the resulting solution was stirred with reflux for 24 hrs.The solution was cooled and evaporated and concentrated under reduced pressure to give a yellow solid. The solid wasdissolved in methanol (MeOH) (1 mL) and 25 % sodium methoxide (NaOMe) (186 mL, 6.212 mmol) and guanidinhydrochloride (498.0 mg, 6.212 mmol) were added dropwise to the resulting solution. And then, the solution was stirredwith reflux for 24 hrs and cooled. The solution was diluted with ethylacetate (EA) and washed with water, and the organicsolvent was dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated and concentrated under reducedpressure to give the title compound (20.3 mg, 55 %).1H NMR (400 MHz, CDCl3) delta 8.50 (s, 1H), 8.43 (s, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.35 (d, J = 7.6 Hz, 1H), 4.07 (s, 3H).

The synthetic route of 1256811-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 82090-52-6, Adding some certain compound to certain chemical reactions, such as: 82090-52-6, name is Imidazo[1,2-a]pyridin-2-ylmethanol,molecular formula is C8H8N2O, 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 82090-52-6.

Example 21; N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(imidazo[1,2-a]pyridin-2- ylmethoxy) pyrimidine-5-carboxamide A mixture of N- {5-[(cyclopropylanaino) carbonyl]-2-methylphenyl}-2- (methylsulfonyl) pyrimidine-5-carboxamide (120mg, 0. 32mmol), imidazo [1, 2-a] pyridine-2- methanol (48mg, 0. 32mmol) and potassium carbonate (44mg, 0. 32mmol) in THF (5mL) was heated to 67C for 3.5 h. The mixture was cooled to room temperature and partitioned between DCM and water and the layers separated. The aqueous layer was extracted with DCM and the combined organic extracts dried (Mg04), filtered and concentrated at reduced pressure to give a yellow oil. This material was purified by silica column chromatography, eluting with a gradient of 0 to 8% methanol in DCM to give the title compound as a white solid (33 mg, 23%); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.67 (m, 2H), 2.27 (s, 3H), 2. 83 (m, 1H), 5.70 (s, 2H), 7.26 (t, 1H), 7.35 (d, 1H), 7.66 (m, 2H), 7.78 (d, 1H), 7. 83 (d, 1H), 8.30 (s, 1H), 8. 38 (d, 1H), 8. 75 (d, 1 H), 9. 17 (s, 2H), 10.16 (s, 1H) ; Mass Spectrum : M-H- 441, M+H+ 443.

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. 82090-52-6, Imidazo[1,2-a]pyridin-2-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/61465; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 960289-03-6, 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, 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, name: 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, blongs to pyridine-derivatives compound. name: 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one

Preparation 10; 2-(4-Fluoro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridine-7-one; Add tetrakis(triphenylphosphine) palladium(O) (0.075g, 0.065 mmol) to a degassed solution of 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.5 g, 2.15 mmol), 4-fluorophenylboronic acid (0.30 g, 2.15 mmol), and sodium carbonate (0.46 g, 4.30 mmol) in N,N-dimethylformamide (21 mL), methanol (5 mL) and water (1 mL). Heat the reaction at 90 0C for 16 h. Allow the reaction to cool to RT and pour into water (75 mL). Filter the resulting solid and dry in vacuo at 80 0C to give 0.40 g (75%) of the title compound. MS/ES m/z 248.0 [M+H]+ .

The synthetic route of 960289-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146759; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 112110-07-3, 5-(Trifluoromethyl)pyridin-3-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, Quality Control of 5-(Trifluoromethyl)pyridin-3-amine, blongs to pyridine-derivatives compound. Quality Control of 5-(Trifluoromethyl)pyridin-3-amine

1-{r(5S,7S)-2-Oxo-3-(2-propyn-1-yl)-1-oxa-3-azaspiror4.5ldec-7-yllmethyl)-1 H-benzimidazole-6- carbonitrileTo a solution of 5-(trifluoromethyl)-3-pyridinamine (0.150 g, 0.925 mmol) in EtOAc (3 mL) at 0 C was added concentrated HCl (0.5 mL). The reaction mixture was stirred for 10 min, then a solution of sodium nitrite (0.192 g, 2.78 mmol, 3 eq; dissolved in 1 mL of water) was added over 2 min. The reaction mixture was then stirred for 30 min. A solution of sodium azide (0.180 g, 2.78 mmol) (3 eq; dissolved in 1 mL of water) was then added over 5 min. After 1 h, a solution of 10% Na2C03 was added to the mixture to make the solution a pH 9-10. The mixture was then extracted with EtOAc (2 x 10 mL). Organic layers were dried over MgS04, filtered, and concentrated in vacuo. The product was placed in high vacuum for 30 min. 1-{[(5S,7S)-2-oxo-3- (2-propyn-1-yl)-1-oxa-3-azaspiro[4.5]dec-7-yl]methyl}-1 H-benzimidazole-6-carbonitrile was obtained as a low viscosity dark orange oil (100 mg, 57% yield).

The synthetic route of 112110-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem