Tag: M.W:100-200

These common heterocyclic compound, 4054-67-5, name is 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole, 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. Quality Control of 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole

General procedure: A mixture of H2L (0.15 mmol, 0.057 g), phen (0.25 mmol, 0.050 g), Zn(Ac)2·2H2O (0.40 mmol, 0.088 g) and 12 mL H2O was placed in a 25 mL Teflon-lined stainless steel container, heated to 180 C for 72 h,and then cooled to room temperature at a rate of 5 C/h.

The synthetic route of 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Jun; Bai, Chao; Hu, Huai-Ming; Yuan, Fei; Xue, Gang-Lin; Journal of Solid State Chemistry; vol. 249; (2017); p. 87 – 97;,
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. 118430-74-3, name is 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine

Example 161 Synthesis of N4-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-9H-pyrimido[4,5-b]indole-2,4-diamine (Cpd. No. 206) Pd2(dba)3 (18 mg) and BINAP (26 mg) were mixed in anhydrous toluene. And the mixture was heated at reflux for 3-4 minutes. This mixture was transferred into a round-bottom flask containing ZBB253 (60 mg), 3-cyclopropyl-1-methyl-1H-pyrazol-5-amine (84 mg), K3PO4 (130 mg), and toluene (2 mL). The mixture was heated at reflux for overnight before quenching with methanol. The reaction mixture was filtered and the mixture was purified by HPLC to yield Cpd. No. 206 as a CF3CO2H salt in 15 mg. ESI-MS calculated for C23H25N8O2 [M+H]+=445.21; Observed: 445.54. 1H NMR (300 MHz, MeOD) delta 7.70 (s, 1H), 7.35 (s, 1H), 6.09 (s, 1H), 3.92 (s, 3H), 3.74 (s, 3H), 2.33 (s, 3H), 2.16 (s, 3H), 1.98-1.88 (m, 1H), 1.03-0.93 (m, 2H), 0.78-0.71 (m, 2H).

The synthetic route of 118430-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 13808-64-5

4-Bromo-1-isopropyl-3-methyl-1H-pyrazole (B2.1) (0353) A mixture of 4-bromo-3-methyl-1H-pyrazole (2 g, 12.5 mmol), 2-iodopropane (6.37 g, 37.5 mmol), Cs2CO3 (6.25 g, 50 mmol) and acetonitrile (30 mL) was stirred at 90 C. for 12 h. The reaction mixture was filtered with MeOH (15 ml) and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (UV214, PE_DMC=100:1 to 50:50) to afford the title compound (700 mg, 56%) as a clear oil. LC-MS: [M+H]+=203.1.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; CHAN, Ho Man; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (134 pag.)US2016/176882; (2016); 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. 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 110860-60-1

18.5 mL of acetic acid is added to 4.1 mL of concentrated sulfuric acid and, while stirring under cooling with ice, 3.85 g (12.1 mmol) of 40% nitrosylsulfuric acid is dropwise added thereto. To the resulting mixture is gradually added 1.71 g (11.0 mmol) of the intermediate (b) (internal temperature: O0C or less), followed by stirring for 2 hours at 0C. 150 mg of urea is added to this reaction solution, followed by stirring for further 15 minutes at O0C to thereby prepare a diazo solution A.

According to the analysis of related databases, 110860-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; WO2009/110643; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1780-72-9, name is 4-Bromo-5-methyl-1H-pyrazol-3-amine, 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. COA of Formula: C4H6BrN3

To a solution of 2H-pyrazol-3-ylamine (2.3 mmol, 1 eq) in acetic acid (3 mL) was added 2-ethoxymethylene-malonic acid diethyl ester (500 muL, 2.5 mmol, 1.1 eq). The mixture was heated at 120 C. for 20 h in a sealed tube. After cooling, the precipitate was filtered and washed with ethanol to afford the expected compound (from 30% to 80% yield). [0595] The expected compound was obtained according to general procedure C step 1 using 4-bromo-5-methyl-2H-pyrazol-3-ylamine. The expected compound was isolated as pale yellow powder. [0596] MS: 300.0 [0597] Mp: decomposes at 270 C.-275 C.

The synthetic route of 4-Bromo-5-methyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; European Molecular Biology Laboratory; F. Hoffmann-La Roche AG; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SAUVAITRE, Thibault; SIMON, Celine; MORICE, Christophe; GIETHLEN, Bruno; LANGER, Thierry; SMITH, Mark; SO, Sung-Sau; CLASSEN-HOUBEN, Dirk; BUSCHMANN, Helmut; US2013/317022; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5744-68-3, name is 5-Bromo-3-methyl-1H-pyrazole, 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 5744-68-3, name: 5-Bromo-3-methyl-1H-pyrazole

(1) Preparation of Compound IIIa: Compound IV (160g, 1mol) was added to 900ml of tetrahydrofuran,Was slowly added portionwise sodium tert-butoxide (115.2g, 1.2mol), stirred for 20 minutes, a solution of iodine benzene (243.6g, 1.2mol). The mixture was heated at reflux for 4 hours with stirring, and then stirred at room temperature overnight, TLC showed the reaction was complete, the reaction mixture was slowly poured into ice water, ethyl acetate was added, the organic phase was separated, the aqueous phase was again extracted with ethyl acetate, the organic phases combined, dried and concentrated to give compound IIIa205.3g, a yield of 87percent.

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, 5-Bromo-3-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hunan HuaTeng Pharmaceutical Co., Ltd; Chen, Fangjun; Li, Shuyun; (8 pag.)CN105330604; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3112-31-0, 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. 3112-31-0 name is 1H-Pyrazole-3,5-dicarboxylic 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.

(A mixture of Dy2O3 (0.187g, 0.5mmol), CuSO4·5H2O (0.125g, 0.5mmol), H3PDC (0.174g, 1.0mmol) and H2O (10mL) was stirred in air for 1h, and then was sealed in a Parr Teflon-lined stainless-steel bomb and heated at 160°C for 3 d, cooled down to room temperature (r.t.) at 2°Ch?1 before the furnace was switched off. The resulting purple, columnar crystals of 1 (ca. 0.30mm in length and 0.20nm in diameter) were collected after washing with water (yield: 76percent, based on CuSO4·5H2O). Elem. Anal. Calcd for C10H16CuDy2N4O19S: C 13.10, H 1.79, N 6.11. Found: C 13.13, H 1.82, N 6.09. IR (KBr pellet cm?1): 3445(s), 1621(s), 1598(s), 1509(m), 1393(m), 1328(s), 1276(m), 1138(w), 1063(w), 1014(w), 853(w), 782(w).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-3,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Wang, Min; He, Liang; Lin, Qipu; Journal of Solid State Chemistry; vol. 265; (2018); p. 29 – 35;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 58607-90-2,Some common heterocyclic compound, 58607-90-2, name is Ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O3, 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.

[00230] To a solution of ethyl 5-oxo-4,5-dihydro-1 H-pyrazole-3-carboxylate (9.5 g , 60.8 mmol) in DCM and DMF (Volume: 1 25.5 ml, Ratio: 7:1 ) was added imidazole (6.21 g, 91 mmol) and TBDMSCI (1 0.09 g, 66.9 mmol) at 0 C. The reaction mixture was warmed up to room temperature and stirred for overnight. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered off, and dried in vacuo. The crude product was used for the next step without further purification. LCMS (m/z) : 271 [M+H]+. 1 H NMR (500 MHz, CDCI3) : (0402) 6.16 (s, 1 H), 4.37 (d, J=7.09 Hz, 2H), 1 .38 (t, J=7.09 Hz, 3H) , 0.98 (s, 9H), 0.27 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Jiping; HAN, Wooseok; JIN, Xianming; PFISTER, Keith Bruce; YOUNG, Joseph Michael; (68 pag.)WO2019/123285; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 15878-00-9,Some common heterocyclic compound, 15878-00-9, name is 4-Chloro-1H-pyrazole, molecular formula is C3H3ClN2, 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.

Example 83 trans-4-Chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide Sodium hydride (60% in oil; 57 mg, 1.43 mmol) was added to a solution of 4-chloro-pyrazole (148 mg, 1.43 mmol) in dry DMF (25 mL) under nitrogen at 0 C. in an ice-water bath and the mixture was heated to 40 C. for 1 h. trans-5-Chloro-1-cyclopropyl-1H-pyrazole-4-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (60 mg, 0.18 mmol) was added and the mixture was heated at 110 C. overnight and then cooled. After the DMF was evaporated in vacuo, water and dichloromethane were added. The organic layer was separated, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were concentrated in vacuo and the residue was purified by C-18 reverse phase preparative-HPLC with a gradient of 10-90% acetonitrile/water to give trans-4-chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (56 mg, 77%). LRMS m/z calcd for C20H24ClN5O2 (M+H) 402.2, found 402.2.

The synthetic route of 15878-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin William; Fotouhi, Nader; Gillespie, Paul; Goodnow, Robert Alan; Guertin, Kevin Richard; Haynes, Nancy-Ellen; Myers, Michael Paul; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Rossman, Pamela Loreen; Scott, Nathan Robert; Thakkar, Kshitij Chhabilbhai; Tilley, Jefferson Wright; Zhang, Qiang; US2007/225280; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 64517-88-0, A common heterocyclic compound, 64517-88-0, name is 1,3-Dimethyl-1H-pyrazol-4-amine, molecular formula is C5H9N3, 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.

[6]; 2-(6-Chlorobenzotriazol-l-yl)-l,l,353-tetramethyluronium tetrafluoroborate was used in place of 2-(7-azabenzotriazol-l-yl)-l,l,353-tetramethyluronium hexafluorophosphate(V) as the coupling agent. The product gave the following characterising data :- 1H NMR Spectrum: (DMSOd6) 2.12 (s, 3H), 3.66 (s, 2H), 3.7 (s, 3H), 3.78 (s, 3H)5 4.02 (s, 3H)5 6.51 (d, IH), 6.88 (m, IH)5 7.03 (d, IH), 7.22 (s, IH)5 7.35 (d, IH)5 7.81 (s, IH), 8.77 (d, IH)5 9.43 (s, 2H); Mass Spectrum: M+H+ 434.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics