Tag: M.W:100-200

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. 19959-77-4, name is 2-(5-Methyl-1H-pyrazol-3-yl)pyridine, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

To a solution of 2-(5-methyl-1H-pyrazol-3-yl)pyridine (27.9 g, 175 mmol) in carbon tetrachloride (300 mL) and dicholoromethane (300 mL) in a round-bottom flask was added N-bromosuccunimide (31.2 g, 175 mmol). The resulting mixture was stirred at room temperature for 21 hours and the reaction mixture was added water. The resulting solution was extracted with dicholomethane. The organic extracts were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with hexane/AcOEt (v/v =10/1) and dried under reduced pressure at 50 C. The title compound was obtained as a white solid. (37.5 g, 158 mmol, 90% yield): 1H NMR (400 MHz, CDCl3) d 8.61 (d, J = 3.1 Hz, 1H), 8.28 (d, J = 7.8 Hz, 1H), 7.80 (t, J = 7.8 Hz, 1H), 7.28 (t, J = 7.8 Hz, 1H), 2.34 (s, 3H).

According to the analysis of related databases, 19959-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fukuda, Takeshi; Goto, Riki; Kiho, Toshihiro; Ueda, Kenjiro; Muramatsu, Sumie; Hashimoto, Masami; Aki, Anri; Watanabe, Kengo; Tanaka, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 16; (2017); p. 3716 – 3722;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 96450-53-2, 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. 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

As shown in step 20-i of Scheme 20, 2-(5,6-dimethoxypyridin-3-yl)-6-(lH- pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-¾]pyridin-5-one [Compound 70, 100 mg, 0.2964 mmol, prepared from 2-chloro-6-(lH-pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-¾]pyridin-5- one and 2,3-dimethoxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (Compound 2021) in a manner similar to the preparation of compound 135 as shown in Example 12], and cesium carbonate (193 mg, 0.593 mmol), were weighed into a conical microwave vial equipped with a stir bar. DMF (1.05 mL) was added followed by the addition of l-(2- chloroethyl)pyrazole ( 77 mg, 0.593 mmols). The vial was sealed and heated at 120C for 15 minutes. Water (3 mL) was added and the resulting precipitate collected by filtration and washed with 5 mL of water. The filtrate was concentrated under reduced pressure. Each of the collected solid and the residue from concentration of the filtrate was diluted with DMSO until solubilized and purified by reversed-phase HPLC to give 6-(l-(2-(lH-pyrazol-l- yl)ethyl)-lH-pyrazol-4-yl)-2-(5,6-dimethoxypyridin-3-yl)-6,7-dihydro-5H-pyrrolo[3,4- 6]pyridin-5-one (Compound 171, 22 mg, 0.05 mmol, 17% yield): ESMS (Mu+Eta) 432.0; 1H NMR (DMSO-de, 300 MHz) delta 8.47 (d, J = 2.0 Hz, 1H), 8.10 (s, 2H), 7.95-7.87 (m, 2H), 7.75 (s, 1H), 7.45 (d, J = 2.2Hz, 1H), 7.40 (d, J = 1.3 Hz, 1H), 6.12 (t, J = 2.0 Hz, 1H), 4.84 (s, 2H), 4.50 (s, 4H), 3.88 (s, 3H), 3.85 (s, 3H).

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, 1-(2-Chloroethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 113808-86-9 as follows. Computed Properties of C6H8N2O2

Example 139: 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1 -ylmethyl]- thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate To a solution of 3,5-dimethyl-1 H-pyrazole-4-carboxylic acid (18 mg, 0.13 mmol), HOBt*H2O (0.13 mmol), N-Methylmorpholine (1 mmol), 4-Dimethylaminopyridine (0.01 mmol) in 0.75 ml_ of DMF, a solution of intermediate 5 (0.1 1 mmol in 1 ml_ DMF) was added followed by EDC (neat, 0.13 mmol). The tube was closed with a screw cap and shaken over night at 40 C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to preparative RP-HPLC purification to give 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1 -ylmethyl]- thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate as a colorless film (33 mg, 52%). 1 H NMR (DMSO-d6, 500 MHz) d ppm 9.22 (t, 1 H), 8.1 (d, 1 H), 7.80 (d, 1 H), 7.30 (bs, 1 H), 6.90 (d, 1 H), 6.69 (s, 1 H), 4.6 (bs, 2H), 4.40 (bs, 2H), 4.3-3.7 (broad signal, 4H), 3.7 (s, 3H), 3.5-3.0 (broad signal, 4H), 2.13 (s, 6H). LC/MS (Method 3); Rt = 1 .15 min; detected mass: m/z = 469.31 ([M+H]+)

According to the analysis of related databases, 113808-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI; MENDEZ-PEREZ, Maria; BREITSCHOPF, Kristin; LORENZ, Katrin; STROBEL, Hartmut; WANG, Li-hsing; SCHIFFER, Alexander; GOERLITZER, Jochen; WO2015/82474; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 39205-87-3, name is 3-Nitro-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Formula: C4H2N4O2

EXAMPLE 7 3-(1-Ethyl-3-nitro-4-pyrazolyl)-acrylic acid 20 g. 3-nitro-4-pyrazole-carbonitrile are stirred with 17.5 ml. ethyl iodide, 21 g. potassium carbonate and 145 ml. 1,2-dimethoxyethane for 2 hours under reflux, followed by cooling. The inorganic material is then filtered off with suction. The filtrate is evaporated in a vacuum, the evaporation residue is dissolved in about 250 ml. ethyl acetate and this solution is shaken up with 150 ml. aqueous 2N potassium carbonate solution and with sodium thiosulphate solution. The organic phase is separated off, dried and evaporated in a vacuum to give 21.7 g. crude 1-ethyl-3-nitro-4-pyrazole carbonitrile in the form of an oil. 15.7 g.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Boehringer Mannheim GmbH; US4105772; (1978); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 920006-32-2, 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. 920006-32-2 name is 1-Isopropylpyrazole-5-carboxylic Acid, This 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 HATU (0.253 g) in DMF (3 ml) was added 1 -(1 -methylethyl)-1 H-pyrazole- 5-carboxylic acid (0.102 g) and DIPEA (0.21 1 ml) and the mixure was left to stand for 10 min. 6-(1 H-lndol-4-yl)-1 H-indazol-4-amine (0.075 g) dissolved in DMF (3 ml) was added and the solution was left to stand at RT for 18 h. DMF was removed by blow down (not to dryness) and the residue was dissolved in chloroform (1 ml) and loaded onto an aminopropyl SPE (2 g) (pre-conditioned with methanol (6 ml) and chloroform (6 ml)). The mixure was left on the column for 2 h then eluted with ethyl acetate:methanol (1 :1 , 10 ml). The solvent was blown down to dryness and the residue was dissolved in DMSO:methanol (1 ml, 1 :1 ) and purified by MDAP (method A). The solvent was removed in vacuo and dried in an vacuum oven (50 C) overnight to give title compound, 18 mg. LCMS (method A) Rt = 3.23 min, MH+ = 385.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Isopropylpyrazole-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian, Robert; DOWN, Kenneth, David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie, Nicole; LE, Joelle; LUNNISS, Christopher, James; PARR, Nigel, James; RITCHIE, Timothy, John; ROBINSON, John, Edward; SIMPSON, Juliet, Kay; SMETHURST, Christian, Alan, Paul; WO2011/67364; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 111573-59-2, name is 3-(Dimethoxymethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 111573-59-2

2.3 kg of formic acid at 0-15 degrees Celsius was slowly added dropwise to 13.8 kg of Compound 3 in 15 L of water.Subsequently, the reaction mixture was magnetically stirred at 25 C for 12 hours,After the reaction was light yellow solid precipitation,Filter the 10 L water and wash the filter cake to obtain 643 g yellow solid compound 4.

According to the analysis of related databases, 111573-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan Yao Ming Kant, Immanuel New Drug Development Co., Ltd.; Xu Xueqin; Zhou Qiang; An Ziqiang; Liu Yueling; He Yanping; Jiao Jiasheng; Wang Ruiqi; Wu Yan; Xu Fujun; Yu Lingbo; Ma Rujian; (6 pag.)CN107235982; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2820-38-4, A common heterocyclic compound, 2820-38-4, name is 3,5-Dimethyl-1H-pyrazol-4-ol, molecular formula is C5H8N2O, 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.

A mixture of 3,5-dimethyl- lH-pyrazol-4-ol (386 mg, 3.44 mmol), N-( – bromopropyl)phthalimide (1.16 g, 3.78 mmol), Cs2C03 (2.24 g, 6.88 mmol) and acetone (20 mL) was heated at reflux for 16 h. The mixture was filtered and concentrated under reduced pressure to give a thick oil, which was purified by flash chromatography (90% EtOAc/petroleum spirits) gave the title compound (290 mg, 25%). 1H NMR (400 MHz, CDC13) delta 2.07 (2 H, dd, 7 13.6, 6.4 Hz, CH2CH2N), 2.19 (6 H, s, 2 x CH3), 3.86 (4 H, td, 7 6.6, 4.7 Hz, CH2N,CH20), 7.67 (2 H, dd, 7 5.4, 3.1, AR), 7.81 (2 H, dd, 7 5.5, 3.1 HZ, Ar);13C NMR (100 MHz, CDC13) delta 9.85, 29.24, 35.43, 72.04, 123.25, 132.13, 133.99, 134.61, 138.93, 168.39; HRMS (ESI+): m/z 300.1341 [M+H]+ (calcd. [Ci6Hi7N303+H]+ 300.1343).

The synthetic route of 2820-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE FLOREY INSTITUTE OF NEUROSCIENCE AND MENTAL HEALTH; THE UNIVERSITY OF MELBOURNE; WILLIAMS, Spencer John; JARROTT, Bevyn; (94 pag.)WO2016/149765; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 96450-53-2, These common heterocyclic compound, 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole, 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.

A solution of Boc methylenedioxybenzenesulfonamide free phenol (0.010 g, 0.020 mmol) in acetone (1 ML) was combined with cesium carbonate (0.015 g, 0.047 mmol), 1-(2-chloroethyl)pyrazole (0.004 9, 0.031 mmol) and sodium iodide (~1 mg, 0.007 mmol).The solution was heated to 55 C. with stirring for 60 hours, and was cooled and dried in vacuo to give a yellow oil.Flash column chromatography (1:3 ethyl acetate/hexane) gave Boc methylenedioxybenzenesulfonamide ethylpyrazole tethered product (0.0015 g, 13%) as a colourless oil: Rf=0.20 (1:1 ethyl acetate/hexane); coupled LCMS showed the product as a single major peak with m/z 631 [M+H]+ at RT of 1.65 min.

The synthetic route of 96450-53-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated.; US2004/122000; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 113808-86-9,Some common heterocyclic compound, 113808-86-9, name is 3,5-Dimethylpyrazole-4-carboxylic Acid, molecular formula is C6H8N2O2, 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 solution of 3,5-dimethyl-1H-pyrazole-4-carboxylic acid (18 mg, 0.13 mmol), HOBt*H2O (0.13 mmol), N-Methylmorpholine (1 mmol), 4-Dimethylaminopyridine (0.01 mmol) in 0.75 mL of DMF, a solution of intermediate 5 (0.11 mmol in 1 mL DMF) was added followed by EDC (neat, 0.13 mmol). The tube was closed with a screw cap and shaken over night at 40 C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to preparative RP-HPLC purification to give 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1-ylmethyl]-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate as a colorless film (33 mg, 52%). 1 H NMR (DMSO-d6, 500 MHz) d ppm 9.22 (t, 1 H), 8.1 (d, 1 H), 7.80 (d, 1 H), 7.30 (bs, 1 H), 6.90 (d, 1 H), 6.69 (s, 1 H), 4.6 (bs, 2H), 4.40 (bs, 2H), 4.3-3.7 (broad signal, 4H), 3.7 (s, 3H), 3.5-3.0 (broad signal, 4H), 2.13 (s, 6H). LC/MS (Method 3); Rt = 1.15 min; detected mass: m/z = 469.31 ([M+H]+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethylpyrazole-4-carboxylic Acid, its application will become more common.

Reference:
Patent; SANOFI; The designation of the inventor has not yet been filed; EP2881390; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 4027-57-0, name is Ethyl 5-methylpyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 5-methylpyrazole-3-carboxylate

Reference 4 Preparation of 3-formyl-5-methylpyrazole; Under nitrogen environment, 3-ethoxycarbonyl-5-methylpyrazole (1.0 g, 4.34 mmol) was dissolved in 15 ml of purified toluene, and DIBAL (8.68 ml, 8.62 mmol) was slowly added and stirred at -78C. The reaction progress and completion were confirmed using TLC (hexane : EtOAc = 6 : 1). Upon completion of the reaction, MeOH and water were slowly added to the reaction mixture and the resulting mixture was filtered through a celite bed, and the aqueous layer was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography (hexane : EtOAc : CH2Cl2 = 3 : 1 : 1) to obtain the title compound. Yield: 82.4% 1H NMR (300 MHz, CDCl3) delta 9.92 (s, 1H), 6.68 (s, 1H), 2.82 (s, 3H)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Korea Institute of Science and Technology; EP1757590; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics