Tag: M.W:100-200

Application of 10165-86-3 , The common heterocyclic compound, 10165-86-3, name is Methyl 6-formylnicotinate, molecular formula is C8H7NO3, 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.

Example 151C methyl 6-[(1S,3E)-3-[4-(difluoromethoxy)-2-hydroxyphenyl]-1-hydroxy-3-{[(S)-2-methylpropane-2-sulfinyl]imino}propyl]pyridine-3-carboxylate A solution of diisopropylamine (280 muL, 1.965 mmol) in tetrahydrofuran (8 mL) was cooled to 0° C., treated dropwise with 2.5 M n-butyllithium in hexanes (720 muL, 1.801 mmol), stirred at 0° C. for 30 minutes, cooled to -78° C., treated dropwise with a solution of Example 151B (687 mg, 1.637 mmol) in tetrahydrofuran (4 mL), stirred at -78° C. for 45 minutes, treated dropwise with a solution of methyl 6-formylnicotinate (270 mg, 1.637 mmol) in tetrahydrofuran (4 mL), stirred at -78° C. for 1 hour, allowed to warm to -10° C. for 1 hour, treated dropwise with a solution of acetic acid (281 muL, 4.91 mmol) in tetrahydrofuran (1 mL) and partitioned between ethyl acetate (30 mL) and saturated NaHCO3 solution (5 mL). The ethyl acetate layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel, eluting with a gradient of 15percent 100percent ethyl acetate in heptanes to provide products that contained the silyl protecting group (first eluting), followed by the title compound that eluted later. The fractions containing the silyl protecting group were combined, concentrated to dryness, dissolved in tetrahydrofuran (10 mL) under N2, cooled to 0° C., treated with 1 M tetra-n-butylammonium fluoride in tetrahydrofuran (1637 mul, 1.637 mmol) and stirred at 0° C. for 1 hour. The mixture was partitioned between methyl tert-butyl ether (50 mL) and 5percent citric acid solution (25 mL). The methyl tert-butyl ether layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel, eluting with a gradient of 15percent to 100percent ethyl acetate in heptanes to provide more of the title compound. The two portions of title compound were combined to provide 192 mg of title compound. 1H NMR (501 MHz, CDCl3) delta 13.00 (s, 1H), 9.18 (d, J=1.6 Hz, 1H), 8.22 (dd, J=8.2, 2.1 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.54 (d, J=9.1 Hz, 1H), 6.63 (d, J=2.4 Hz, 1H), 6.54 (t, J=73.1 Hz, 1H), 6.47 (dd, J=9.0, 2.5 Hz, 1H), 5.33 (q, J=5.3 Hz, 1H), 4.90 (d, J=5.3 Hz, 1H), 3.96 (s, 3H), 3.80-3.74 (m, 2H), 1.40 (s, 9H); LC/MS (ESI+) m/z 471 (M+H)+.

The synthetic route of 10165-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55676-21-6, 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 55676-21-6, name is 1-(2-Chloropyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 1-(2-chloropyridin-3-yl)ethanone (B-2) (6 g, 38.6 mmol) and hydrazine (85%, 9.1 g, 154.4 mmol) in pyridine (80 mL) was stirred under reflux overnight. The mixture was cooled to room temperature, concentrated, diluted with water (80 mL) and then extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine, dried over Na2S04, and concentrated under vacuo. The resulting residue was used for the next step without furtuer purification. MS (m/z): 134 (M+1 )+

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 55676-21-6, 1-(2-Chloropyridin-3-yl)ethanone.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1008-91-9, Adding some certain compound to certain chemical reactions, such as: 1008-91-9, name is 1-(Pyridin-4-yl)piperazine,molecular formula is C9H13N3, 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 1008-91-9.

General procedure: 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 1.2 equivalents) was added to a solution of the corresponding alpha-methyl carboxylic acid (2) (1 equiv), the appropriate amine (1.5 equiv) and DIEA (2 equiv) in dry acetonitrile (10 mL) at room temperature under argon atmosphere. The reaction mixture was stirred at room temperature overnight. Solvent was evaporated under reduced pressure, and the crude product was purified using a Teledyne Isco Combiflash Rf purification machine using 0-10% CHCl3/methanol as eluent to provide the desired amides 3-59 in 68-95% yields.

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. 1008-91-9, 1-(Pyridin-4-yl)piperazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mathew, Bini; Snowden, Timothy S.; Connelly, Michele C.; Guy, R. Kiplin; Reynolds, Robert C.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 12; (2018); p. 2136 – 2142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6980-08-1, 4-Chloro-3-nitropyridin-2-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, Computed Properties of C5H4ClN3O2, blongs to pyridine-derivatives compound. Computed Properties of C5H4ClN3O2

Dry DMSO (20 mL) was added to NaH (1.029 g of a 60% dispersion in mineral oil, 25.7 mmol) in a round bottom flask under argon. After 5 minutes, solid fert-butyl 2-fluoro-4- hydroxyphenylcarbamate (5.59 g, 24.6 mmol) was added in three portions, giving a dark solution, which, after 15 minutes of stirring at room temperature, was treated with 4-chloro-3-nitropyridin-2-amine (4.23 g, 24.4 mmol) at once. The dark red solution was heated to 0C for 1 hour and allowed to cool down to room temperature. EtOAc (150 mL) and H20 (200 mL) were subsequently added to the solution and the organic layer was isolated. The aqueous layer was extracted with EtOAc (3 x 100 mL) and the combined organic layers were washed once with saturated NaHC03 (150 mL), dried (MgS04), filtered, and concentrated to dryness to give a bright yellow solid. This material was used in the next step without further purification.Yield: 8.68 g (98%). 1H-NMR (DMSO-d6), delta (ppm), J (Hz): 1.46 (s, 9H, C(CH3)3), 6.08 (d, 1 H, PyrH), 7.01 (m, 1 H, ArH), 7.18 (br s, 2H, NH2), 7.22 (m, 1 H, ArH), 7.67 (m, 1 H, ArH), 8.04 (d, 1 H, PyrH), 9.03 (s, 1 H, NHBoc); 19F-NMR (DMSO-d6), delta (ppm): -120.7; LC-MS (4.72 min): m/z calcd. for C,6H17FN405 [M+H+]: 365.0; found:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6980-08-1, 4-Chloro-3-nitropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL (THE); SPRINGER, Caroline; NICULESCU-DUVAZ, Ion; MARAIS, Richard; NICULESCU-DUVAZ, Dan; ZAMBON, Alfonso; MENARD, Delphine; WO2011/92469; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 149806-06-4, 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.149806-06-4, name is 6-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.01, as common compound, the synthetic route is as follows.

6-bromo-pyridine-3-carbaldehyde (5 g, 26.9 mmol, 1.0 eq.) and 4-ethyl-piperidine was dissolved in dichloromethane (100 ml), stirred for 2 hours, acetic acid was added portionwise inside borohydride sodium (6.2 g, 29.2 mmol, 1.1 eq). After 16 hours of reaction, an aqueous solution of sodium hydroxide was added thereto 2 mol/L to adjust the PH to alkaline, extracted with dichloromethane, and concentrated under reduced pressure to give a white solid of 1-(6-bromopyridin-3-yl)methyl-4-ethylpiperidine (6.98g, yield: 91.4%).

The chemical industry reduces the impact on the environment during synthesis 149806-06-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Kaisheng Beite Pharmaceutical Co., Ltd.; Cai, Xiong; Qian, Changgeng; Liu, Bin; Li, Junqi; Lin, Mingsheng; Qing, Yuanhui; Weng, Yunwo; Wang, Yanyan; Xue, Weicai; You, Huajin; Zhou, Shiqing; (67 pag.)CN105622638; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1101120-05-1 , The common heterocyclic compound, 1101120-05-1, name is 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, molecular formula is C9H5N3O, 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.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

The synthetic route of 1101120-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
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. 62733-99-7, name is Methyl 3-hydroxypicolinate. A new synthetic method of this compound is introduced below., Safety of Methyl 3-hydroxypicolinate

To a solution of 3-hydroxy-pyridine-2-carboxylic acid methyl ester (200 mg, 1.3 mmol) in N,N-dimethylformamide (2.0 ml) was added at 22 C. sodium hydride (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0 C. and treated with trifluoroethyl trifluoromethanesulfonate (728 mg) and stirring was continued at 22 C. for 2 hours. The mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate, and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane and ethyl acetate (3:1) as the eluent to give 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester as a pale green oil. Mass (calculated) C9H8F3NO3 [235.16]; (found) [M+H]+=236.

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, 62733-99-7, Methyl 3-hydroxypicolinate.

Reference:
Patent; Andreini, Matteo; Banner, David; Guba, Wolfgang; Hilpert, Hans; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Roger-Evans, Mark; Travagli, Massimiliano; Valacchi, Michela; Woltering, Thomas; Wostl, Wolfgang; US2011/46122; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15871-85-9 , The common heterocyclic compound, 15871-85-9, name is 2-Methoxypyridine-5-carbonitrile, molecular formula is C7H6N2O, 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.

B) 6-methoxynicotine acid To a solution of 6-methoxynicotinonitrile (5.00 g) in ethanol (100 mL) was added 2 M aqueous potassium hydroxide solution (20 mL). The reaction mixture was heated at reflex for 2 hr, and the solvent was evaporated under reduced pressure. To the residue was added water, the pH of the mixture was adjusted to 4-5 with 2 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (4.2 g). 1H NMR (400 MHz, DMSO-d6) delta 3.92 (3H, s), 6.86-6.92 (1H, m), 8.11-8.15 (1H, m), 8.73 (1H, d, J = 2.0 Hz), 13.0 (1H, s).

The synthetic route of 15871-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIKAMI, Satoshi; NAKAMURA, Shinji; ASHIZAWA, Tomoko; SASAKI, Shigekazu; TANIGUCHI, Takahiko; NOMURA, Izumi; KAWASAKI, Masanori; EP2848618; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 21543-49-7, 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. 21543-49-7, name is 2-Chloro-5-hydroxymethylpyridine, molecular formula is C6H6ClNO, 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.

To a solution of 2-chloro-5-hydroxymethylpyridine (0.45 g, 0.003 mole) in DCM (10 mL) at 0 C under N2, was added phosphorus tribromide (0.44 mL, 0.0037 mole) drop wise. Reaction mixture was warmed to RT and stirred for 1.5 hours. The reaction mixture was diluted with DCM (75 mL), treated with saturated aqueous sodium bicarbonate (20 mL). Organic layer was washed with water (20 mL), brine solution (20 mL) and dried over Na2S04 and concentrated under vacuum to obtain the title compound. Yield: 0.49 g; lH – NMR (CDC13, 400 MHz) delta ppm: 4.35 (s, 2H), 7.32 – 7.34 (d, J = 8.2 Hz, 1H), 7.69 – 7.71 (dd, J = 2.2, 7.9 Hz, 1H), 8.40 – 8.41 (d, J = 1.7 Hz, 1H); Mass (m/z): 205.9, 208.0 (M+H)+.

According to the analysis of related databases, 21543-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; BADANGE, Rajesh Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (172 pag.)WO2018/42362; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 68325-15-5, 3-Chloro-4-cyanopyridine, 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: C6H3ClN2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3ClN2

Intermediate 1 : lsoxazolo[5,4-c1pyridin-3-ylamine.; To a solution of 3-chloro-isonicotinitrile (1.13 g, 8.36 mmol) in DMF (6.0 mL) were added potassium carbonate (1.69 g, 12.2 mmol) and acetohydroxamic acid (0.91 g, 12.2 mmol). The reaction mixture was stirred at rt overnight, diluted with EtOAc (200 mL) and extracted with saturated aqueous NaHCO3 (200 mL) then saturated aqueous NaCI (100 mL). The aqueous layers were back extracted with EtOAc (200 mL) and the combined organic layers were dried (MgSO4) and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give isoxazolo[5,4-c]pyhdin-3-ylamine (0.447 g, 41 %). MS (ESI+): calcd for C6H5N3O m/z 135.04, found 136.2 (M+H)+. 1H NMR (d6-DMSO): 8.93 (d, J = 0.8, 1 H), 8.45 (d, J = 5.2, 1 H), 7.88-7.86 (dd, J = 5.2, 1.2, 1 H), 6.72 (br s, 2H).

The synthetic route of 68325-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68453; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem