Category: 920966-03-6

Park, Eunsun; Lee, Sun Joo; Moon, Heegyum; Park, Jongmi; Jeon, Hyeonho; Hwang, Ji Sun; Hwang, Hayoung; Hong, Ki Bum; Han, Seung-Hee; Choi, Sun; Kang, Soosung published the artcile< Discovery and Biological Evaluation of N-Methyl-pyrrolo[2,3-b]pyridine-5-carboxamide Derivatives as JAK1-Selective Inhibitors>, Formula: C8H5ClN2O2, the main research area is methyl pyrrolopyridine carboxamide preparation Janus kinase inhibitor mol docking.

Janus kinase 1 (JAK1) plays a key role in most cytokine-mediated inflammatory and autoimmune responses through JAK/STAT signaling; thus, JAK1 inhibition is a promising therapeutic strategy for several diseases. Anal. of the binding modes of current JAK inhibitors to JAK isoforms allowed the design of N-alkyl-substituted 1-H-pyrrolo[2,3-b] pyridine carboxamides I (R = H, Me, cyclopropyl, cyclopentyl) as a JAK1-selective scaffold, and the synthesis of various Me amide derivatives e.g., II, provided III as a potent JAK1-selective inhibitor. In particular, the (S,S)-enantiomer of III exhibited excellent potency for JAK1 and selectivity over JAK2, JAK3, and TYK2. On investigating the effect of III on hepatic fibrosis, it was found that it reduces the proliferation and fibrogenic gene expression of TGF-β-induced hepatic stellate cells (HSCs). Specifically, III significantly inhibited TGF-β-induced migration of HSCs at 0.25μM in wound-healing assays.

Journal of Medicinal Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 920966-03-6 belongs to class pyridine-derivatives, and the molecular formula is C8H5ClN2O2, Formula: C8H5ClN2O2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Nakajima, Yutaka; Tojo, Takashi; Morita, Masataka; Hatanaka, Keiko; Shirakami, Shohei; Tanaka, Akira; Sasaki, Hiroshi; Nakai, Kazuo; Mukoyoshi, Koichiro; Hamaguchi, Hisao; Takahashi, Fumie; Moritomo, Ayako; Higashi, Yasuyuki; Inoue, Takayuki published the artcile< Synthesis and evaluation of 1H-pyrrolo[2,3-b]pyridine derivatives as novel immunomodulators targeting Janus kinase 3>, COA of Formula: C8H5ClN2O2, the main research area is pyrrolopyridine preparation Janus kinase inhibitor lipophilicity mol docking pharmacokinetics.

A series of 1H-pyrrolo[2,3-b]pyridine derivatives I [R = H, Me, c-Hex, Ph; R1 = NHCH(CH2CH3)2, piperidin-1-yl, ((1S,2R)-2-methylcyclohexyl)aminyl, cyclohexylaminyl, etc.] as novel immunomodulators targeting JAK3 for use in treating immune diseases such as organ transplantation has been described. In the chem. modification of N-cyclohexyl-N-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine, the introduction of a carbamoyl group to the C5-position and substitution of a cyclohexylamino group at the C4-position of the 1H-pyrrolo[2,3-b]pyridine ring led to a large increase in JAK3 inhibitory activity. Compound I [R = H, R1 = ((1S,2R)-2-methylcyclohexyl)aminyl] was identified as a potent, moderately selective JAK3 inhibitor, and the immunomodulating effect of I [R = H, R1 = ((1S,2R)-2-methylcyclohexyl)aminyl] on interleukin-2-stimulated T cell proliferation was shown. Docking calculations and WaterMap anal. of the 1H-pyrrolo[2,3-b]pyridine-5-carboxamide derivatives I were conducted to confirm the substituent effects on JAK3 inhibitory activity.

Chemical & Pharmaceutical Bulletin published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 920966-03-6 belongs to class pyridine-derivatives, and the molecular formula is C8H5ClN2O2, COA of Formula: C8H5ClN2O2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 920966-03-6, 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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Preparation 59To a suspension of 4-chloro-lH-pyrrolo [2, 3-b]pyridine-5-Carboxylic acid (343 mg) in N,N-dimethylformamide (4 ml) was added phenylmethanol (375 mul) 4-dimethylaminopyridine (428 nig) and N- [3- (dimethylamino) propyl] -N’ -ethylcarbodiimide hydrochloride (676 mg) . After stirring at ambient temperature for 3 days, the reaction mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform to give benzyl 4-chloro-lH-pyrrolo[2,3-b]pyridine-5-carboxylate (200 mg) as a yellow powder. 1H-NMR(DMSO-d6)OrS.40(2H,s) , 6.6 (IH, d, J=I.8Hz) , 7.35-7.39 (3H,m) , 7.41-7.45 (2H,m) ,7.71 (IH, d, J=3.5Hz) , 8.75 (IH, s) , 12.42 (IH, br) . EPO MS(ESI) :m/z 297.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,920966-03-6, 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 920966-03-6 ,Some common heterocyclic compound, 920966-03-6, molecular formula is C8H5ClN2O2, 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.

The compound 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 11a (1.00 g, 5.10 mmol) and DMF (10 mL) were added to the reaction flask, was added CDI (0.91g, 5.61mmol), stirred at room temperature for 1 hour and ice-water bath, followed by addition of NH3.H2O (1.12mL) at 0 C, stirred at room temperature for 1 hour. TLC monitored the reaction was complete, the system was poured into water, extracted three times with ethyl acetate, washed with water, and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated, dichloromethane / petroleum ether = 5ml / 1ml beating, suction filtration, dried under reduced pressure using a rotary evaporator to give the title compound 11b (0.6g, 3.08mmol), in a yield of 60.3%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,920966-03-6, its application will become more common.

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 920966-03-6 ,Some common heterocyclic compound, 920966-03-6, molecular formula is C8H5ClN2O2, 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.

The compound 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 11a (1.00 g, 5.10 mmol) and DMF (10 mL) were added to the reaction flask, was added CDI (0.91g, 5.61mmol), stirred at room temperature for 1 hour and ice-water bath, followed by addition of NH3.H2O (1.12mL) at 0 C, stirred at room temperature for 1 hour. TLC monitored the reaction was complete, the system was poured into water, extracted three times with ethyl acetate, washed with water, and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated, dichloromethane / petroleum ether = 5ml / 1ml beating, suction filtration, dried under reduced pressure using a rotary evaporator to give the title compound 11b (0.6g, 3.08mmol), in a yield of 60.3%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,920966-03-6, its application will become more common.

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 920966-03-6, Adding some certain compound to certain chemical reactions, such as: 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid,molecular formula is C8H5ClN2O2, 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 920966-03-6.

To a solution of carboxylic acid 14 in methylene chloride under an atmosphere of nitrogen was added 1.5 equivalents of oxalyl chloride followed by catalytic amount of dimethylformamide. The reaction was stirred for 18 hours before the addition of an excess of methanol. After 2 hours stiffing the reaction was evaporated to dryness to give the title compound 15 as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.87 (s, 3H) 6.62-6.63 (m, 1H) 7.68-7.69 (m, 1H) 8.68-8.70 (m, 1H) 12.37 (s, 1H).

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. 920966-03-6, 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Helicon Therapeutics, Inc.; US2012/95016; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 920966-03-6, 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.920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, molecular formula is C8H5ClN2O2, molecular weight is 196.59, as common compound, the synthetic route is as follows.

Preparation 32To a solution of 4-chloro-lH-pyrrolo[2, 3-b]pyridine-5- carboxylic acid (840mg) inN,N-dimethylformamide (8.4mL) were added 1-hydroxybenzotriazole (808 mg) and 1- (3-dimethylaminopropyl) – 3-ethylcarbodiimide (929 mg) . The mixture was stirred at 600C for 30 minutes. The solution was cooled to ambient temperature and added EPO 28% ammonium hydroxide aqueous solution (1.2 ?iL) . The mixture was stirred at ambient temperature for 1 hour. To the solution were added water and chloroform and the mixture was extracted with chloroform.The extract was dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-chloro- lH-pyrrolo [2, 3-b]pyridine-5-carboxamide (90 mg) as a pale yellow powder.1H-NMR (DMSO-d6) delta : 6.55-6.57 (lH,m) , 7.63-7.66 (lH,m) , 7.90 (2H,br) ,8.2 9(lH,s) ,12.16(lH,brs) .MS (ESI) :m/z 218(M+Na)+.

Statistics shows that 920966-03-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Quality Control of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

To a stirred solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.8 g, 4.06 mmol) in propan-2-ol (20 mL) was added concentrated sulphuric acid (0.5 mL) at 0 C. and the reaction mixture was stirred at 80 C. for 12 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude product was dissolved in water, basified with saturated bicarbonate and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (20% ethyl acetate/hexane) to provide isopropyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate as a white solid (0.3 g, 33% yield): MS (ES) m/z 239.1 (M+H).

The synthetic route of 920966-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACLARIS THERAPEUTICS, INC.; ANDERSON, David Randolph; HOCKERMAN, Susan Landis; BLINN, James Robert; JACOBSEN, Eric Jon; US2019/135807; (2019); 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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Quality Control of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

To a stirred solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.8 g, 4.06 mmol) in propan-2-ol (20 mL) was added concentrated sulphuric acid (0.5 mL) at 0 C. and the reaction mixture was stirred at 80 C. for 12 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude product was dissolved in water, basified with saturated bicarbonate and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (20% ethyl acetate/hexane) to provide isopropyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate as a white solid (0.3 g, 33% yield): MS (ES) m/z 239.1 (M+H).

The synthetic route of 920966-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACLARIS THERAPEUTICS, INC.; ANDERSON, David Randolph; HOCKERMAN, Susan Landis; BLINN, James Robert; JACOBSEN, Eric Jon; US2019/135807; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, molecular formula is C8H5ClN2O2, 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. Formula: C8H5ClN2O2

To a solution of carboxylic acid 14 in methylene chloride under an atmosphere of nitrogen was added 1.5 equivalents of oxalyl chloride followed by catalytic amount of dimethylformamide. The reaction was stirred for 18 hours before the addition of an excess of methanol. After 2 hours stiffing the reaction was evaporated to dryness to give the title compound 15 as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.87 (s, 3H) 6.62-6.63 (m, 1H) 7.68-7.69 (m, 1H) 8.68-8.70 (m, 1H) 12.37 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 920966-03-6.

Reference:
Patent; Helicon Therapeutics, Inc.; US2012/95016; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem