Category: pyrazoles-derivatives

Synthetic Route of 113808-86-9, 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. 113808-86-9, name is 3,5-Dimethylpyrazole-4-carboxylic Acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 11; [4-(5-{3-[(1-Acetyl-piperidine-4-carbonyl)-(3-chloro-4-methyl-phenyl)-amino]-propyl}-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-3,5-dimethyl-pyrazol-1-yl]-acetic acid trifluoro acetate (II-18); step 1-; A mixture of 3,5-dimethyl-1H-pyrazole-4-carboxylic acid (820 mg; CAS Reg No. 113808-86-9), 11a (2.42 g), TEA (2.2 mL) and PyBOP (5.84 g) in DMF (15 mL) was stirred at RT overnight. The reaction was quenched by addition of water and partitioned between water and EtOAc. The organic layer was separated and washed 3 times with water and once with brine, dried (MgSO4), filtered and evaporated. The residue was purified via SiO2 chromatography eluting with DCM/MeOH/NH4OH to afford 0.829 g of 62a.

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, 3,5-Dimethylpyrazole-4-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lemoine, Remy; Melville, Chris Richard; Rotstein, David Mark; Wanner, Jutta; US2007/191335; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 1-Isopropylpyrazole-5-carboxylic Acid

DIPEA (94 pL, 0.57 mmol) was added to a stirred solution of Intermediate 56 (70 mg, 0.19 mmol), 1 -(propan-2-yl)- 17/-pyrazolc-5-carboxylic acid (44 mg, 0.28 mmol) and HATU (112 mg, 0.29 mmol) in DCM (2.5 mL) at r.t. The reaction mixture was stirred at r.t. for 18 h, then diluted with water (5 mL) and extracted with DCM (3 x 15 mL). The combined organic phases were separated using a hydrophobic PTLE frit, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, using a gradient of fc/7-butyl methyl ether in heptane (0-80%), to afford the title compound (61 mg, 65%) as a white solid. 5H (250 MHz, DMSO-de) 10.12 (s, 1H), 8.45 (d, J8.2 Hz,1H), 7.70-7.66 (m, 1H), 7.50 (d, 1.9 Hz, 1H), 7.43-7.33 (m, 2H), 7.12 (d, J5.6 Hz, 1H), 6.95 (d, 2.0 Hz, 1H), 6.81 (d, J5.7 Hz, 1H), 5.44-5.34 (m, 1H), 4.37 (t, j 8.5 Hz, 1H), 3.99-3.90 (m, 2H), 3.77-3.67 (m, 2H), 2.11-2.01 (m, 2H), 1.91-1.75 (m, 2H), 1.74-1.65(m, 2H), 1.63-1.56 (m, 1H), l.37 (d, 6.6 Hz, 3H), 1.34 (d, J6.6 Hz, 3H), 1.32-1.26 (m, 1H), 1.25-1.18 (m, 1H), 1.16-1.10 (m, 2H), 1.10-1.01 (m, 1H), 0.92-0.81 (m, 5H). uPLC- MS (method 1): MH+ m/z 491, RT 4.06 minutes.

The synthetic route of 920006-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SRL; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; FOULKES, Gregory; LECOMTE, Fabien Claude; (0 pag.)WO2020/11731; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1269293-48-2, name is Ethyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H9BrN2O2

Step 2b. A solution of compound form step 2a (400 mg, 1.44 mmol), 1,3,5-trichloro- l,3,5-triazinane-2,4,6-trione (700 mg, 3.14 mmol) in MeCN/AcOH/water 15ml (80/3/2) was stirred for 1 hour at -5C before was partitioned (EtOAc-brine). The organic was dried (Na2S04), filtered and concentrated to give the desired compound (500 mg) as a yellow oil. ESI-MS m/z =253.00 [M+H]+. This material was used directly in the next step without further purification.

The synthetic route of 1269293-48-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; QIU, Yao-ling; LI, Wei; CAO, Hui; JIN, Meizhong; GAO, Xuri; PENG, Xiaowen; KASS, Jorden; OR, Yat, Sun; (84 pag.)WO2016/183266; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 81190-89-8, 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. 81190-89-8, name is Methyl 4-bromo-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

[1197] to a mixture of methyl 4-bromo-1H-pyrazole-3-carboxylate (15.0 g, 73.2 mmol,) andCs2CO3 (59.6 g, 182.9 mmol) in DMF(150 ml) was added mel (14.7 ml, 236.0 mmol) drop-wise at 0c under N2. The mixture was stirred at 25 C for 16 hours. The reaction mixture was filtered, the cake washed with ethyl acetate (200 ml x 2). The filtrate was washed with water (70 ml x 4) and the aqueous phase extracted with ethyl acetate (150 ml). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to dryness. The crude product which was purified by fcc (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 50/50) to afford the title compound 240a (8.3 g, yield 51.8%) as a white solid and the title compound 240b (7.0 g, yield 43.7%) as white solid. Compound 240a: 1H NMR (400mhz, CDCl3): delta 7.48 (s, 1h), 4.15 (s, 3h), 3.93 (s, 3h). MS (ESI) m/z (M+H)+ 219.0.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-1H-pyrazole-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 89260-46-8, 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. 89260-46-8 name is 3-(1H-Pyrazol-3-yl)aniline, 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.

A cooled (0 0C) solution of 6-(cyclopropylmethyl(propyl)amino)pyrimidine-4- carboxylic acid (Intermediate 21 , 112 mg; 0.45 mmol) in DCM was treated with diisopropylethylamine (78.4 mL; 0.52 mmol) and methyl chloroformate(36.2 mL; 0.47 mmol). After stirring at 0 0C for 15 minutes, 3-(1 H-pyrazol-3- yl)aniline (Apollo, 107 mg; 0.67 mmol) was added and the mixture stirred for 72 hours. The solvent was evaporated and the compound purified by preparative HPLC to give the title compound as a white solid. 1H NMR (400MHz, CDCI3) delta 10.08 (1 H, br s), 8.58 (1 H, s), 8.19 (1 H, s), 7.76 (1 H, d, J = 8.0 Hz), 7.64 (1 H, d, J = 2.3 Hz), 7.57 (1 H, d, J = 7.7 Hz), 7.49- 7.34 (2H, m), 6.67 (1 H, d, J = 2.3 Hz), 3.53 (4H, s), 1.75-1.63 (2H, m), 1.09 (1 H, s), 0.97 (3H, t, J = 7.4 Hz), 0.57 (2H, d, J = 7.7 Hz), 0.35-0.29 (2H, m). MS (ESI-) 375. HPLC (Condition C) Rt 3.75 min (HPLC purity 99.9%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(1H-Pyrazol-3-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; LABORATOIRES SERONO SA; WO2009/19167; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 84547-87-5, 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 84547-87-5 as follows.

(c) 3,8-Dichlorodipyrazolo[T .5-a; 1 ‘,5’-d]pyrazine-4,9-dior.eA mixture of 4-chloropyrazole-3-carboxylic acid (2.0 mmol, 300 mg; see step (b) above) in tbionyl chloride (25 mL) was heated at reflux for 3 days. The excess thionyl chloride was removed in vacuo and the crude product employed in the next step without purification.

According to the analysis of related databases, 84547-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOLIPOX AB; WO2007/45868; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3273-44-7,Some common heterocyclic compound, 3273-44-7, name is 5-Methyl-1H-pyrazole-3-carbaldehyde, molecular formula is C5H6N2O, 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 5-methyl-1H-pyrazole-3-carbaldehyde (Werner A. et al., Tetrahedron, 51, 4779 (1995): 1.1 g) in acetonitrile (20 mL), triethylamine (1.5 mL) and chlorotriphenylmethane (3.1 g) were added and mixed for 12 hours. The reaction solution was concentrated, and the residue was dissolved in chloroform. This solution was washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with a silica gel column to give the title compound (1.9 g) as a colorless solid. NMR (CDCl3) delta: 1.54 (3H, s), 6.66 (1H, s), 7.09-7.17 (6H, m), 7.25-7.34 (9H, m), 9.83 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-pyrazole-3-carbaldehyde, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1669352; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, belongs to pyrazoles-derivatives compound, 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 25700-12-3, SDS of cas: 25700-12-3

0398-1 Iodine (208 mg) and ammonium cerium nitrate (450 mg) were added to a solution of 3-(1H-pyrazol-1-yl)pyridine (200 mg) in acetonitrile (3 mL), followed by stirring at room temperature for 13 hours, and stirring for 8 hours under heating to reflux. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added thereto. The organic layer was collected by separation, washed sequentially with a 10% sodium hydrogen sulfite aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 3-(4-iodo-1H-pyrazol-1-yl)pyridine (333 mg). MS m/z (M+H): 272.

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.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 916766-83-1, 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. 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of methyl1H-pyrrolo[3,2-b]pyridine-3-carboxylate (2.2 g, 12.50mmol), 3-[4-(chloromethyl)phenyl]-1-methyl-1H-pyrazole(3.04 g, 12.5 mmol), and KOH (1.4 g, 25.0 mmol) in acetone (80 mL) was stirredat 50 C for 18 h. The reaction mixture was concentrated, diluted with 100 mLof H2O, and neutralized to pH 7 with 6.0 M aq. HCl. The aq. mixture was extracted with EtOAc (2 x100 mL), and the combined extracts were dried (Na2CO3),filtered, and concentrated to afford 4.3 g (99%) of intermediate 7a as a yellow solid. Intermediate 7a was used in the following step without additional purification.

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, 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Davoren, Jennifer E.; O’Neil, Steven V.; Anderson, Dennis P.; Brodney, Michael A.; Chenard, Lois; Dlugolenski, Keith; Edgerton, Jeremy R.; Green, Michael; Garnsey, Michelle; Grimwood, Sarah; Harris, Anthony R.; Kauffman, Gregory W.; Lachapelle, Erik; Lazzaro, John T.; Lee, Che-Wah; Lotarski, Susan M.; Nason, Deane M.; Obach, R. Scott; Reinhart, Veronica; Salomon-Ferrer, Romelia; Steyn, Stefanus J.; Webb, Damien; Yan, Jiangli; Zhang, Lei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 650 – 655;,
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. 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 916766-83-1

To a mixture of 3- ( (3S, 4S) -4-hydroxytetrahydro-2H-pyran- 3-yl) -7-methyl-6- (4,4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl ) – 2H-benzo [e] [1, 3] oxazin-4 (3H) -one (0.10 g), 3-(4- (chloromethyl) phenyl) -1-methyl-lH-pyrazole (0.06 g) ,tetrakis (triphenylphosphine) alladium (0) (15 mg) , and DME (3 mL) was added 2 M aqueous sodium carbonate solution (0.26 mL) at room temperature, and the mixture was stirred under an argon atmosphere at 80C overnight. The reaction mixture was diluted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethylacetate/hexane) and crystallized from ethyl acetate to give the title compound (0.05 g) .XH NMR (300 MHz, DMSO-d6) delta 1.33-1.64 (1H, m) , 1.81-1.96 (1H, m) , 2.24 (3H, s) , 3.31-3.50 (2H, m) , 3.64-3.73 (1H, m) , 3.75- 3.84 (1H, m) , 3.86 (3H, s) , 3.87-4.01 (4H, m) , 5.06 (1H, d, J = 5.3 Hz), 5.18-5.39 (2H, m) , 6.62 (1H, d, J = 2.3 Hz), 6.89 (1H, s), 7.14 (2H, d, J = 8.3 Hz), 7.54 (1H, s) , 7.65-7.73 (3H, m) .

According to the analysis of related databases, 916766-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics