Tag: M.W:200-300

Application of 148038-83-9, 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.148038-83-9, name is 6-Bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one, molecular formula is C6H4BrN3O, molecular weight is 214.02, as common compound, the synthetic route is as follows.

A. 6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine Reflux 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (5 g) for 14 h in POCl3 (50 mL). Evaporate the solvent in vacuo, then carefully neutralize with saturated NaHCO3, and extract with EtOAc. Dry over Na2SO4, concentrate under vacuum, and purify by flash chromatography (1:1 hexanes/EtOAc) to obtain 6-bromo-2-chloro-3H-imidazo[4,5-b]pyridine.

The chemical industry reduces the impact on the environment during synthesis 148038-83-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROGEN CORPORATION; US2003/36652; (2003); 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.119285-07-3, name is tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, molecular weight is 278.3501, as common compound, the synthetic route is as follows.name: tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

To a stirring solution OF CYCLOPENTYL- (4, 6-DICHLORO- [1, 3,5] triazin-2-yl) – amine (0.60g, 2.57 mmol) prepared as in Example 14A above in 5 ML OF acetonitrile was added 4- (5-AMINO-PYRIDIN-2-YL PIPERAZINE-1-CARBOXYLIC acid tert- butyl ester (0.72g, 2.6 mmol) and triethylamine (0.36 mL, 2.6 mmol). The mixture was stirred at ambient temperature. After 20 minutes, solids formed. The solids were filtered off and washed several times with acetonitrile. The solids were dried in a vacuum oven for 1.5 hours at 60C. Purification was accomplished via silica column chromotography in 7: 1 dichloromethane/acetone. The desired fractions were collected and concentrated in vacuo to afford N- Cyclopentyl-N’, N”-BIS- (6-PIPERAZIN-1-YL-PYRIDIN-3-YL)-1, 3,5-triazine-2, 4,6- triamine (Compound B) as a brown foam/solid (0.234g, 19%). Ms 517.3 ; Mp >290.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,119285-07-3, tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/65378; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 778611-64-6, 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. 778611-64-6, name is 5-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, 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.

Step 1 : To a solution of BB-3 (100 mg, 0.287 mmol) in toluene (10 mL), K2C03 (119 mg, 0.86 mmol), 5- bromo-2-chloro-4-methylpyridine (77 mg, 0.373 mmol) and Lambda/,/V -dimethyl ethylene diamine (13 mg, 0.143 mmol) were added and the mixture was degassed through purging with Ar for 30 min. Cul (27 mg, 0.14 mmol) was added and the RM was heated to 100C for 48 h. The RM was chilled, diluted with toluene and filtered over a plug of celite. The volatiles were removed under reduced pressure and the residue was purified by flash CC (silica gel, Hex/EtOAc) to yield the desired compound (60 mg, 45%).

According to the analysis of related databases, 778611-64-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, Felix; RITTER, Stefanie; NORDHOFF, Sonja; WACHTEN, Sebastian; OBERBOeRSCH, Stefan; KLESS, Achim; WO2015/22073; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59281-14-0, 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-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, Computed Properties of C13H13NO3, blongs to pyridine-derivatives compound. Computed Properties of C13H13NO3

To a stirred solution of compound 9b (2.7g) in NaOH solution (0.567g in 55 mL of water) was added 10%Pd-C(l .4g) portion wise under nitrogen atmosphere. The nitrogen was replaced with hydrogen and stirred at RT for 16h. The reaction mass was filtered under celite and concentrated under reduced pressure to give 2.2 g of the required compound as a mixture. Proceeded with crude to the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59281-14-0, 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; VITAS PHARMA RESEARCH PVT LTD; ALAPATI, Chandrasekhar; BANERJEE, Ankita; RANGARAJAN, Radha; KUMAR, Rajinder; WO2014/57415; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 286947-03-3, 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.286947-03-3, name is 5-Bromo-2-chloro-3-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

c. Preparation of Compound To a 25 mL flask containing (63.8 mg, 1.2 mmol) of sodium ethoxide was added 3 mL dry ethanol. The mixture was stirred for 30 minutes. 2-Chloro-3-methoxy-5-bromopyridine (230 mg, 1.04 mmol) was added to the mixture and heated to 60 C for 16 hours. The reaction was allowed to cool and the solvent was removed. Ethyl acetate was added (50 ml) was added to the residue. The ethyl acetate solution was washed with water and then brine. The organic solvent was dried and concentrated, purified by ISCO flash chromatography using 10% ethyl acetate in hexane to give 220 mg (97% yield) of the desired product. NMR (300 MHz, CDC13) delta: 7.71 (s, IH), 7.09 (s, IH), 4.37 (qt, 2H), 3.82 (s, 3H), 1.38 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 286947-03-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; PARHI, Ajit; SAGONG, Hye Yeon; PATEL, Disha; ARNOLD, Eddy; DAS, Kalyan; VIJAYAN, Suyambu Kesava; WO2014/43252; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 82671-06-5, 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 82671-06-5 as follows.

Example 16A (^-Sjdelta-Difluoro^-hydroxy^^i^Kfl.SloxathioIoS^-clpyridin-theta- ylmethyl)amino]-l-piperidinyl}methyI)-4,5-dihydro-7H-pyrrolo[3,2,l-^]-l?5- naphthyridin-7-one dihydrochloride(a) 2-Chloro-5-fluoro-6-(methyloxy)-3-pyridinecarboxylic acidA solution of 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (51.12g, 243 mmol) in methanol (400 ml) was treated with sodium methoxide in methanol (25% w/v, 100 ml, 535 mmol) and the mixture heated to reflux for 4 hours. The cooled mixture was treated with water (400 ml) and acidified to pH2 with aqueous hydrochloric acid (2M) then concentrated to ca 400 ml. Filtration, washing with water and drying in vacuo over P2O5 for 18h afforded the product as a white solid (32.65g, 65%). MS (+ve ion electrospray) m/z 208 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,82671-06-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/71936; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 944401-56-3 ,Some common heterocyclic compound, 944401-56-3, molecular formula is C6H4BrF3N2, 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 mixture of 5-bromo-4-(trifluoromethyl)-pyridin-2-amine (6, 7.47 g, 31 mmol) and DMAP (366 mg, 3.0 mmol) in CH2Cl2 (120 mL) were added triethylamine (8.6 mL, 62 mmol) followed by di-tert-butyl dicarbonate (7.6 mL, 33 mmol) at 0 C. The reaction mixture was stirred at rt for 5 h. The organic solution was washed with water and brine, dried over MgSO4. The organic solvent was removed, and the residue was purified by silica gel chromatography with 1:20 EtOAc/PE to give 7 as white solid (6.67 g, 92% yield, Rf = 0.56 in 1:10 EtOAc/PE). 1H NMR (400 MHz, CDCl3) delta: 9.07 (s, 1H), 8.58 (s, 1H), 8.42 (s, 1H), 1.58 (s, 9H). 13C NMR (100 MHz, CDCl3) delta: 152.3, 152.1, 151.7, 139.4 (q, J = 33 Hz), 121.7 (q, 1JCF = 275 Hz), 110.9 (q, J = 6 Hz), 108.9, 82.3, 28.3. MS (ESI + APCI) m/z: 341.0 [M-H]-, 343.0 [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. 944401-56-3, 5-Bromo-4-(trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Peng, Wei; Tu, Zheng-Chao; Long, Zi-Jie; Liu, Quentin; Lu, Gui; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 644 – 654;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 552331-00-7, Adding some certain compound to certain chemical reactions, such as: 552331-00-7, name is 4-Iodopyridin-2-amine,molecular formula is C5H5IN2, 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 552331-00-7.

Library Protocol 3 To a 0.2M solution of 5-(4,4, 5,5-tetramethyl- 1, 3,2-dioxaborolan-2-yl)-2-[( 1 -{[4-(trifluoromethoxy) phenyl]acetyl}piperidin-4-yl)oxy]benzamide (Preparation 14, 500 p L, 100 pmol) in DMF was added a 0.2M solution of compounds of formula (IV) (500 pL, lOOpmol) in DMF with argon purging. A 2M solution of cesium carbonate (100 pL, 200 pmol) in degassed water was added followed by tetrakis(triphenylphosphine)palladium (0) (5.7 mg, 5 pmol) and the reaction was heated to 130C under microwave irradiation for 15 minutes. The reaction wascooled and concentrated in vacuo. The residue was dissolved in DMSO (1 mL) and purified using preparative HPLC using one of the Purification Methods (PM) below:

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. 552331-00-7, 4-Iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53937-02-3, 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, molecular formula is C12H11NO2, 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.

B) 4- (Benzyloxy) -1- (2-ethyl-l-methyl-lH-benzimidazol-6- yl) pyridin-2 ( 1H) -one A mixture of 4-benzyloxy-2 ( 1H) -pyridone (1 g) , 6-bromo-2- ethyl-l-methyl-lH-benzimidazole (1.19 g) , Nu,Nu’- dimethylethylenediamine (0.530 ml), copper (I) iodide (0.946 g) , potassium carbonate (2.06 g) and DMSO (20 ml) was stirred at 150C for 2 h. The mixture was added to 28% NH3 solution, and the precipitate was collected. The solid was dissolved in THF, passed through NH silica pad and concentrated in vacuo to give the title compound (986 mg) as a pink solid. A part of the target compound was treated with activated carbon and recrystallized from THF to give 46.1 mg of the title compound as a white solid. . MS (ESI+) : [M+H]+ 360.4. XH NMR (400 MHz, DMSO-d6) : delta 1.33 (3H, t, J = 7.4 Hz), 2.90 (2H, q, J = 7.5 Hz), 3.74 (3H, s), 5.16 (2H, s), 5.98 (1H, s) , 6.10 (1H, d, J = 5.4 Hz), 7.07 (lH, d, J = 8.8 Hz), 7.34-7.51 (5H, m) , 7.53 (1H, s) , 7.55-7.62 (2H, m)

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 73870-24-3, name is 4-(Bromomethyl)pyridine hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-(Bromomethyl)pyridine hydrobromide

Sodium hydride {3.0 g, 125 mmol, 10 eq. (5.0 g of 60%> NaH in oil)} was added to a solution of galeterone (1, 5.0 g, 12.9 mmoL, 1 eq.) in THF (80 mL) at 0C under argon atmosphere. A white precipitate formed and after stirring for one minute, DMF (5.0 mL) was added and the reaction mixture was allowed to stir for 10 minutes at room temperature. The reaction mixture was placed at 0C and lithium carbonate (5.0 g, 67.7 mmoL, 5 eq. ) was added, followed immediately by 4-(bromomethyl)pyridine hydrobromide (14, 10 g, 39.5 mmoL, 3 eq.) and the reaction mixture was allowed to stir at 0C for 30 minutes. The reaction mixture was removed from 0C and stirring continued at ambient temperature for 18 hours under argon atmosphere. The color of the reaction mixture changed from clear to dark red during the 18-hour period. After 18 hours, the reaction mixture was placed at 0C, water (30 mL) was added to quench unreacted NaH, and the mixture was stirred for 10 minute. Volatile (THF) were removed in vacuo and water (70 mL) was added to the residue aqueous phase. The aqueous phase was extracted with ethyl acetate (EtOAc) (150 mL x 3). Ethyl acetate extract was washed with brine (80 mL x 2), dried with anhydrous Na2SO4 and concentrated in vacuo to give a dark red crude product. Purification by flash chromatography using 3% MeOH/EtOAc as eluent afforded compound galeterone 3beta-pyridine methoxylate (3) as a white solid (3.78 g, 7.88 mmoL, 61%), mp 177-179C. Rf= 0.31 (5% MeOH/EtOAc).

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, 73870-24-3, 4-(Bromomethyl)pyridine hydrobromide.

Reference:
Patent; UNIVERSITY OF MARYLAND, BALTIMORE; NJAR, Vincent C.O.; PURUSHOTTAMACHAR, Puranik; MURIGI, Francis; (33 pag.)WO2017/223320; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem