Tag: M.W:100-200

Synthetic Route of 55052-27-2, 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.55052-27-2, name is 6-Chloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5ClN2, molecular weight is 152.581, as common compound, the synthetic route is as follows.

To a solution of 7n (2.7 mmol, 410 mg), tetrabutylammonium hydrogen sulfate (3 mol%, 27 mg) and benzene sulfonyl chloride(3.3 mmol, 583 mg) in DCM (15 mL) placed at ice bath was added1N NaOH solutions (3.0 mL). The resulting mixture was stirred atroom temperature for 8 h. Water (30 mL) was added cautiously tothe reaction, and the mixture was extracted with DCM (15mL 3).The combined organic phase was washed with saturated NaCl (aq)for three times, dried over anhydride sodium sulfate and concentratedunder reduced vacuum. The crude product (14a) was directlyused in next step.

Statistics shows that 55052-27-2 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Article; Liu, Bin; Yuan, Xia; Xu, Bo; Zhang, Han; Li, Ridong; Wang, Xin; Ge, Zemei; Li, Runtao; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 1 – 15;,
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.3279-76-3, name is 6-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.Recommanded Product: 3279-76-3

To a solution of 6-methyl-pyridin-2-ol (2.5 g, 0.023 mol) in CH2CI2 (10 mL) at r. t. , under N2, were added AG2CO3 (6 g, 1.5 eq. ) and Mel (5,6 mL, 4 eq). The solution was stirred at r. t. for 4 days, then AG2CO3 was filtered and washed with CH2CI2, and the organic layer was evaporated to dryness. The crude product was purified by flash chromatography (silica gel, EtOAc/cHex 2: 8) to give the title compound (1.9 mg, 67%) as a white solid. NMR (‘H, CDCl3) : 8 7.4 (t, 1H), 6.6 (d, 1H), 6.5 (d, 1H), 3.8 (s, 3H), 2.4 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3279-76-3, 6-Methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6515-09-9, 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.6515-09-9, name is 2,3,6-Trichloropyridine, molecular formula is C5H2Cl3N, molecular weight is 182.4351, as common compound, the synthetic route is as follows.

To Compound 12 (5.47 g, 30 mmol) were added nitric acid (30 mL) and concentrated sulfuric acid (24 mL) at room temperature, and the reaction mixture was warmed up to 100 C. and stirred with heating for approximately 8 hours. The reaction mixture was added to iced water, the resulting mixture was stirred. The precipitated solid was filtered to obtain Compound 13 (6.82 g, 64.7%). Compound 13; Method B [0817] LC/MS retention time=2.03 min.

Statistics shows that 6515-09-9 is playing an increasingly important role. we look forward to future research findings about 2,3,6-Trichloropyridine.

Reference:
Patent; SHIONOGI & CO., LTD.; Tamura, Yuusuke; Kojima, Eiichi; Ikemoto, Hidaka; Hinata, Yu; US2015/203450; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1005785-85-2, 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. 1005785-85-2, name is 5-(tert-Butyl)picolinic acid, molecular formula is C10H13NO2, 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.

A solution of carboxylic acid (80 mg, 0.45 mmol) and CDI (145 mg, 0.90 mmol) in DMF (4 mL) was stirred at rt for 0.5 h, followed by the addition of the amine (110 mg, 0.45 mmol) and Et3N (137 mg, 1.35 mmol) and the mixture was stirred at rt for 16 h. After diluted with water (5 mL), the mixture was extracted with EtOAc (5 mL x 2). The combined organics were concentrated in vacuo and the residue was purified by reverse phase chromatography (MeOH/H2O with 0.05% NH3.H2O as mobile phase) to afford the title compound (26 mg, yield 15%) as a yellow solid. ESI-MS (M+H)+: 400.2.1H NMR (400 MHz, CD3OD) : 8.77-8.74 (m, 2H), 8.06-8.03 (m, 2H), 7.92-7.95 (m, 2H), 7.54-7.51 (m, 2H), 6.86 (d, J = 4.0 Hz, 1H), 4.74 (s, 2H), 2.53 (s, 3H), 1.42 (s, 9H).

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 1005785-85-2, 5-(tert-Butyl)picolinic acid.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52334-51-7, 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.52334-51-7, name is 3-Amino-5-methylpyridin-2(1H)-one, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

(Reference Example 5-2) At room temperature, to a mixed solvent solution of 3-amino-5-methylpyridin-2-ol (4.03 g) in tetrahydrofuran (50 ml) and 1,2-dichloroethane (50 ml) were added tert-butyl 4-oxopiperidine–1-carboxylate (13.04 g), sodium triacetoxyborohydride (13.87 g) and acetic acid (3.75 ml), followed by heating at reflux for 16 hours. After the temperature was brought back to room temperature, 1 N aqueous sodium hydroxide solution was added, and extracted with chloroform. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford tert-butyl 4-[(2-hydroxy-5-methylpyridin-3-yl)amino]piperidine-1-carboxylate (7.6 g). 1H NMR (400 MHz, CDCl3) delta 1.40-1.50 (m, 2H), 1.47 (s, 9H), 1.98-2.10 (m, 2H), 2.06 (s, 3H), 2.92-3.02 (m, 2H), 3.32-3.41 (m, 1H), 3.95-4.10 (m, 2H), 4.78-4.83 (m, 1H), 6.16 (s, 1H), 6.48 (s, 1H), 11.5-11.8 (br m, 1H).

The chemical industry reduces the impact on the environment during synthesis 52334-51-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 119396-04-2, 4-Chloro-2-(chloromethyl)pyridine hydrochloride, 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, 119396-04-2, blongs to pyridine-derivatives compound. Computed Properties of C6H6Cl3N

4-chloro-2-(chloromethyl)pyridine hydrochloride (200 mg, 1.02 mmol) was dissolved in chloroform (15 mL) and cooled in water/ice bath m-chloroperoxobenzoic acid (77%, 350mg, 1.56 mmol) was added and the reaction mixture was stirred for 24 hours while letting towarm up to room temperature. The solvent was evaporated on rotary evaporator and theresidue was purified by flash chromatography on silica in 5% methanol / 95 %dichloromethane mixture, giving 143 mg of the product as white solid (0.803 mmol, 79 % yield).500 MHz): 4.90 (C H2, s, 2H); 7.26 ( arom ., dd, 1H,3/HH= 7 Hz,4/HH = 3 Hz); 7.64 (arom., d, 1H,4/HH= 3 Hz); 8.20 (arom., d, 1H,3/HH= 7 Hz);13C{ NMR (CDCl3, 25 C, 125 MHz): 5c 39.6 (CH2, s); 125.6 (arom., s); 125.9 (arom., s); 132.4 (arom., s); 140.2 (arom., s); 148.7 (arom., s).HRMS (ESI) m/z: [(M + H)+] (C6H6Cl2NO) calculated: 177.9821, found: 177.9820.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,119396-04-2, its application will become more common.

Reference:
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; POLASEK, Miloslav; (102 pag.)WO2019/106182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2739-74-4, 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. 2739-74-4, name is Ethyl 3-(2-Pyridyl)propanoate, molecular formula is C10H13NO2, 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.

Example 5 3-(2-pyridyl)propanoic acid, hydrazide (5) STR16 To a stirring 5 mL EtOH solution of 0.58 g (3.2 mmol) of ethyl 3-(2-pyridinyl)propanoate (4), prepared as described above in Example 4, was added 0.32 g (6.5 mmol) of hydrazine hydrate. The reaction was heated at reflux for three weeks. Although the reaction was still incomplete, the solvent was removed under vacuum. The resulting gum was triturated with diethyl ether (Et2 O). The product remained a gum. The yield of 3-(2-pyridyl)propanoic acid, hydrazide (5) was 0.22 g (42%). This product was used immediately in the manner described in Example 6 below.

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 2739-74-4, Ethyl 3-(2-Pyridyl)propanoate.

Reference:
Patent; G. D. Searle & Co.; US5378840; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16328-62-4, 1H-Imidazo[4,5-b]pyridin-2(3H)-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, Quality Control of 1H-Imidazo[4,5-b]pyridin-2(3H)-one, blongs to pyridine-derivatives compound. Quality Control of 1H-Imidazo[4,5-b]pyridin-2(3H)-one

Under argon, 1 ,3-dihydroimidazo[4,5-b]pyridin-2-one (1.500 g, 1 1.10 mmol) was dissolved in DMF (20 ml_). Then sodium hydride (0.4662 g, 1 1 .66 mmol) was added portion-wise over 15 minutes. The resulting suspension was stirred at room temperature for 1 hour. Then di-tert-butyl dicarbonate (2.47 g, 1 1.10 mmol), dissolved into DMF (16.9 ml_), was added dropwise over 10 minutes and the orange solution obtained was stirred at room temperature for 3 hours. Some MeOH was carefully added to quench the reaction mixture and then water was added. The pH of the solution was 8 to 9. The aqueous layer was extracted once with ethyl acetate and this extract was discarded (removal of impurities) then the pH was adjusted to 7 with 4 M aq. HCI solution and extraction was carried out with ethyl acetate. The combined organic layers were washed with water (x2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure at 40C to afford tert-butyl 2-oxo-3H- im idazo[4 , 5-b] pyrid ine- 1 -carboxylate. NMR (400 MHz, CDCI3): d ppm 8.80-10.50 (br s, 1 H), 8.13 (m, 1 H), 8.00 (dd, J=7.89, 1.28 Hz, 1 H), 7.10 (dd, J=7.89, 5.32 Hz, 1 H), 1.69 (s, 9H). LC-MS: Rt = 0.75 min, MS ES+ = 236 (M+H+).

The synthetic route of 16328-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA CROP PROTECTION AG; BIGOT, Aurelien; SCHAETZER, Juergen, Harry; JUNG, Pierre, Joseph, Marcel; STOLLER, Andre; GAGNEPAIN, Julien, Daniel, Henri; HALL, Roger, Graham; RENDINE, Stefano; COMPAGNONE, Nicola; (122 pag.)WO2020/30503; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 103878-09-7 ,Some common heterocyclic compound, 103878-09-7, molecular formula is C8H9NO3, 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.

To a slurry of (iS,25T)-l-iV-(6-fluoi -l,3-benzothiazoi-2-yl)cyclopentane-l,2-diamine hydrochloride (Intermediate 1; 100 mg, 0.35 mmol) in dry DCM (1.2 ml) was added 3- ethoxypyridine-2-carboxylic acid hydrochloride (Intermediate 5, 78 mg, 0,38 mmol), HATU (198 mg, 0.52 mmol) and triethyiamine (145 mu, 1.04 mmol). The reaction mixture was stirred at room temperature for 17 hours then partitioned between DCM and a saturated solution of sodium bicarbonate. The organics were filtered through a (0581) hydrophobic frit and concentrated in vacuo. The crude material was purified by reverse phase preparative HPLC (eluted with acetonitriie / water containing 0.1 % ammonia) to afford the title compound. (0582) 1H MR (400 MHz, DCM-cfc) delta ppm 1.43 – 1.55 (m, 3 H), 1.64 – 1.77 (m, 2 H), 1.86 – 1.98 (m, 2 H), 2.23 – 2.36 (m, 1 H), 2.45 – 2.60 (m, 1 H), 3.96 – 4.09 (m. 1 H), 4.10 – 4.23 (m, 2 H), 4.31 – 4.48 (m, 1 H), 6.94 – 7.07 (m, 1 H), 7.24 – 7.33 (m, 1 H), 7.35 – 7,46 (m, 3 H), 8.06 – 8.24 (m, 2 H) (0583) MS ES+: 401

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,103878-09-7, its application will become more common.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; FUJIMOTO, Tatsuhiko; ROBINSON, John Stephen; WO2015/124934; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 72716-80-4 ,Some common heterocyclic compound, 72716-80-4, molecular formula is C8H8N2O, 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: To a solution of substituted 2-oxo-1,2-dihydropyridines (3.36 mmol), zinc oxide (0.30 g, 3.70 mmol),zinc chloride (0.50 g, 3.70 mmol), N,N-diisopropylethylamine (0.48 g, 3.70 mmol), 1,4-dioxane (15 mL)was added benzyl chloride (0.58 g, 4.04 mmol) under argon atmosphere. The mixture was heated in 110 C oil bath with rapid stirring for the indicated time. The reactor was cooled to room temperature,and the insoluble residue was filtered off through celite, and the cake was wash with ethyl acetate(30 mL). The filtrate was washed with water (10 mL 2), once with brine (10 mL), dried overmagnesium sulfate, filtered, and concentrated in vacuo to afford crude product. The product was purified by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:20) to yield thecorresponding compounds.

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. 72716-80-4, 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Qifan; Du, Fangyu; Liang, Xinjie; Liu, Wenqiang; Fang, Ting; Chen, Guoliang; Molecules; vol. 23; 7; (2018);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem