Tag: M.W:200-300

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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C12H12N2O2

Example 33 2-Ethyl-5-phenyl-2H-pyrazole-3-carboxylic Acid Ethyl Ester To a 0 C. mixture of the above-prepared 5-phenyl-2H-pyrazole-3-carboxylic acid ethyl ester (350 mg, 1.62 mmoles) and iodoethane (260 muL, 3.23 mmoles) in DMF (3 mL) was added neat LiH (spatula tip, excess) under a nitrogen atmosphere. The resulting mixture was warmed up to room temperature and stirred overnight. The crude reaction was cooled to 0 C., quenched with aqueous NH4Cl, diluted with ethyl acetate and enough water to dissolve all solids. The phases were separated, and the organic phase was washed sequentially with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The regioisomeric products separated and purified by flash chromatography (silica gel, hexanes/ethyl acetate gradient) to give the title compound (167 mg, 42% yield, higher Rf in hexanes/ethyl acetate) and the undesired regioisomer (175 mg, 44% yield) as white solids. 1H NMR (CDCl3, 400 MHz): 7.81 (d, 2H); 7.40 (dd, 2H); 7.29 (dd, 1H); 7.13 (s, 1H); 4.63 (q, 2H); 4.37 (q, 2H); 1.47 (t, 3H); 1.41 (t, 3H).

The synthetic route of 13599-12-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US6608087; (2003); B1;,
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. 84547-84-2, name is 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 84547-84-2

A mixture of 4-bromo- 1 -methyl- 1 H-pyrazole-5-carboxylic acid (5.0 g, 24.4 mmol) and BH3.THF (36.6 mL of a 1 M solution in THF, 36.6 mmol) in THF (50 mL) was stirred at 50 C for 2 days; at this point LCMS showed the completion of the reaction. The reaction was cooled to RT and cautiously quenched with aq. 1N HC1 and stirred at RT for 1 h, after which the mixture was extracted with EtOAc (3 X 50 mL). The combined organic extracts were concentrated in vacuo. The residue was chromato graphed (80 g Si02; continuous gradient from 0% to 100% EtOAc in hexanes, 25 min) to give the title compound (3.60 g, 18.9 mmol, 77 % yield) as a white solid. LCMS, [M+H]+ = 193.0.

The synthetic route of 84547-84-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); 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. 1191616-45-1, name is 4-(4-Bromophenyl)-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C10H9BrN2

Into a 500-mL 3-necked round-bottom flask, were placed 4-(4-bromophenyl)- 1-methyl-1H-pyrazole (3.80 g, 16.0 mmol) and tetrahydrofuran (50 mL). This was followed by the addition of n-BuLi (7.00 mL, 74.3 mmol) dropwise with stirring at -80 C within 5 min. To this was added 1-benzyl-5-bromo-N- methoxy-N-methyl-1 H-indazole-3-carboxamide (2.00 g, 5.34 mmol, synthesis see below). The resulting solution was stirred for 150 min at -80 C. The reaction was then quenched by the addition of 50 mL of ice water. The resulting solution was extracted twice with 50 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuo. The residue was applied onto a silica gel column with dichloromethane/methanol (100/1). This resulted in 1.70 g (60%) of 5- bromo-3-[[4-(1-methyl-1 H-pyrazol-4-yl)phenyl]carbonyl]-1-(1-phenylpentyl)- 1 H-indazole as a yellow solid.

The synthetic route of 1191616-45-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LTD.; SCHIEMANN, Kai; (173 pag.)WO2016/41618; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 141573-95-7, A common heterocyclic compound, 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C8H10F2N2O2, 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 aniline compound (la to Id) (leq.) and DFMMP (1 eq.), both dissolved in an inert solvent were added to a suspension of a base (1.5 eq.) in the inert solvent at 0C. The conversion of aniline to anilide was followed by GC analyses.

The synthetic route of 141573-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOLVAY SA; BRAUN, Max, Josef; WO2012/55864; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 30169-25-6, 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. 30169-25-6 name is 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine, 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 3,6-bis(3,5-dimethylpyrazolyl)-1,2,4,5-tetrazine (2.72 g, 10.0 mmol) in MeCN (10 mL) was added DNAZ.HCl (1.83 g, 10.0 mmol) and triethylamine (1.11 g, 11 mmol). The resulting solution was stirred for 1 hour until the color had changed to a uniform orange-red color. Diethyl ether (20 mL) was added and the precipitate was collected via filtration. The precipitate was washed with water (3×10 mL) and diethyl ether (2×10 mL). Recrystallization of the crude material from MeCN led to isolation of DMPTzDNAZ (2, 2.50 g, 78%) as orange-red crystals. Anal. Calcd for C10H11N9O4: C, 37.39%; H, 3.45%; N, 39.24%. Found: C, 37.73%; H, 3.42%; N, 38.89%. 1HNMR (400 mHz, d6-DMSO) delta 2.24 (s, 3H, CH3), 2.46 (s, 3H, CH3), 5.28 (s, 4H, DNAZ), 6.26 (s, 1H, pyr). 13CNMR (400 mHz, d6-DMSO) delta 12.67 (CH3), 13.37 (CH3), 59.71 (DNAZ), 107.95 (DNAZ), 109.50 (pyr), 141.88 (pyr), 151.10 (pyr), 157.71 (tz), (Tz), 162.58 (tz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine, and friends who are interested can also refer to it.

Reference:
Patent; Los Alamos National Security, LLC; Chavez, David E.; Hanson, Susan Kloek; Scharff, Robert Jason; Veauthier, Jacqueline Marie; Myers, Thomas Winfield; (40 pag.)US9902748; (2018); B2;,
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. 398491-59-3, name is tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H16N4O2

Ib (500 mg, 2.23 mmol) was dissolved in 10 ml of tetrahydrofuran,683 mul of triethylamine was added followed by 200 mul of methanesulfonyl chloride,After reaction at room temperature for 2 h, the solvent was removed under reduced pressure,Column chromatography (P: E = 1: 1) gave white solid 1c (487 mg, 72%).

The synthetic route of 398491-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Ruichuang Zhiyuan Biological Technology Co., Ltd.; Qiao Dehua; (27 pag.)CN106279177; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1146629-77-7,Some common heterocyclic compound, 1146629-77-7, name is (4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, molecular formula is C15H17N5O2, 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.

37 in acetonitrile (514mg, 1.72mmol, Lin, Q. et al. Org. Lett., 2009, 11, to a solution (15mL) of the is preparation) described in 1999-2002, 44 (537mg, 4.29mmol), followed by the addition of DBU (540muL, 3.61mmol). The reaction was stirred at room temperature for 15 hours, then concentrated under reduced pressure. The resulting mixture of crude was diluted with water and extracted with ethyl acetate (3 x 50mL). The combined organic layers were washed with 1N HCl, dried (Na2SO4), filtered, and concentrated in vacuo. Normal phase column chromatography (SiO 2, 0~60% ethyl acetate / hexanes) Purification on to give a white foam (+/-)-45 (368mg, 50%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, its application will become more common.

Reference:
Patent; Concert Pharmaceuticals Inc.; Ai, Robert Silverman; Julie, F. Liu; Adam, J. Morgan; Bhomick, Panda; Scott, EL. Habeson; (43 pag.)JP2015/117185; (2015); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1146629-77-7, name is (4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, 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 1146629-77-7, Formula: C15H17N5O2

37 in acetonitrile (619mg, 2.07mmol, Lin, Q. et al. Org. Lett., 2009, 11, to a solution (15mL) of the is preparation) described in 1999-2002, 51 (673mg, 5.17mmol), followed by the addition of DBU (650muL, 4.35mmol). The reaction was stirred for 15 hours at room temperature, and concentrated under reduced pressure. The resulting mixture of crude was diluted with water, and extracted with ethyl acetate (3x50mL). The combined organic layers were washed with 1N HCl, dried (Na2SO4), filtered and concentrated under reduced pressure. Normal phase column chromatography (SiO2, 0~60% ethyl acetate / hexanes) Purification on to give a white foam (+/-)-52 (447mg, 50%).

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; Concert Pharmaceuticals Inc.; Ai, Robert Silverman; Julie, F. Liu; Adam, J. Morgan; Bhomick, Panda; Scott, EL. Habeson; (43 pag.)JP2015/117185; (2015); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, 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 Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

To the toluene layer was added 25% caustic soda solution159 g (0.994 mole) of the compound were added thereto, and the mixture was heated to 65 DEG C and stirred for 45 minutes. The aqueous layer was separated, and 54 g of water and 160.2 g (1.54 mole) of 35% hydrochloric acid were added to the toluene layer, followed by stirring at 85 for 15 minutes. After cooling to room temperature the resulting crystals were filtered, washed with 180 g of water and dried in vacuo at 60 & lt; RTI ID = 0.0 & gt;To obtain 155.8 g (yield 98%) of 3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxylic acid.

The synthetic route of Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buheung Industries Co., Ltd.; Ahn, Kyung Wook; Kim, Jong Nam; Wang, Kyu Jung; Noh, Dong Won; Seo, Nan Young; Kim, Sin Ae; Wei, Sung Han; (10 pag.)KR2016/120009; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 37687-24-4, The chemical industry reduces the impact on the environment during synthesis 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, I believe this compound will play a more active role in future production and life.

[00590] 7rt-Butyl-[(2R)-2-hydroxypropyl]carbamate (6.46 g, 36.86 mmol) was added to a stirred solution of diethyl-3,5-pyrazoledicarboxylate (3.9 g, 18.43 mmol), triphenylphosphine (8.7 g, 33.18 mmol) and DTBAD (7.64 g, 33.18 mmol) in THF (150 mL) at 0 C. The mixture was stirred at 80 C for 16 h. The solvent was then evaporated in vacuo, the crude product purified first by open column chromatography (silica; DCM 100%) and then by flash column chromatography (silica, DCM in Heptane 0/100 to 100/0 and then EtOAc in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield diethyl-l- {(l*5)-2-[(tert-butoxycarbonyl)amino]-l- methylethyl}-lH-pyrazole-3,5-dicarboxylate as a white (7.6 g, 20% purity, 22 % yield).

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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P., Jeffrey; LINDSLEY, Craig, W.; STAUFFER, Shaun, R.; BARTOLOME-NEBREDA, Jose Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; TONG, Han Min; ALCAZAR-VACA, Manuel Jesus; ANDRES-GIL, Jose Ignacio; WO2013/192350; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics