Category: pyrazoles-derivatives

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

Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, COA of Formula: C4H6N2

To a mixture of 1-methyl-1H-pyrazole (16.4 g, 0.2 mol, 1.0 eq) in dry THF (150 mL) was added n-BuLi (2.5 M in hexane, 96 mL, 0.24 mol, 1.2 eq) at -78 C. under nitrogen atmosphere. The mixture was stirred at -78 C. for 1 h. Then DMF (30.8 mL, 0.4 mol, 2.0 eq) was added dropwise and the mixture was stirred for 1 h. TLC analysis of the reaction mixture showed full conversion to the desired product. The reaction was quenched with a saturated aqueous solution of NH4Cl and extracted with EA (3×500 mL). The organic layer was washed with brine and water, dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on a silica gel to give compound OI-5a (12.7 g, 58%).

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-Methylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Foresee Pharmaceuticals Co., Ltd.; YANG, Wenjin; CHANG, Kai-Wei; LIU, Suying; TSAI, Cheng-Han; (98 pag.)US2019/352288; (2019); 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. 930-36-9, name is 1-Methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Methylpyrazole

To a solution of 1 -methyl pyrazole (4.1 g, 50 mmole) in THF (100 mL) at 00C was added n-BuLi (2.2M in THF, 55 mmole). The reaction solution was stirred for 1 hour at RT and then cooled to -78C [J. Heterocyclic Chem. 41 , 931 (2004)]. To the reaction solution was added 2-isopropoxy-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (12.3 mL, 60 mmole). After 15 min at -78C, the reaction was allowed to warm to 00C over 1 hour. The reaction was diluted with saturated NH4CI solution and extracted with DCM. The organics were dried over Na2SO4 and concentrated under vacuum to afford a tan solid (8.0 g, 76%) which was used without further purification. LCMS (ES) m/z 127 (M+H)+ for [RB(OH)2]; 1H NMR (CDCI3, 400 MHz) delta 7.57 (s, 1 H), 6.75 (s, 1 H), 4.16 (s, 3H), and 1.41 (s, 12H).

The synthetic route of 930-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/98105; (2008); 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

Reference of 63874-95-3, 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. 63874-95-3 name is 1-Benzyl-1H-pyrazole-4-carbaldehyde, 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.

General procedure: To a solution of Example 13 (53 mg, 0.17 mmol, 1.0 eq) and 1-methyl-1H-imidazole-2-carbaldehyde (28 mg, 0.25 mmol, 1.5 eq) in THF (2 mL) under a N2 atmosphere was added NaBH(OAc)3 (72 mg, 0.34 mmol, 2.0 eq) and the mixture was stirred at RT overnight. The mixture was purified by C18 reverse phase column (Biotage, 30% to 70% ACN in water, 0.1% TFA) to afford the title compound (22 mg, 34%) as a white solid. LCMS: [M+H]+ 384.2. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=8.4 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.41 (s, 2H), 7.20 (s, 1H), 4.78 (s, 2H), 3.98 (s, 3H), 3.80 (s, 2H), 3.40 (m, 2H), 3.17-3.00 (m, 3H), 2.59 (s, 3H), 2.24 (m, 2H), 1.95 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Benzyl-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Ribon Therapeutics Inc.; Schenkel, Laurie B.; Vasbinder, Melissa Marie; Kuntz, Kevin Wayne; Swinger, Kerren Kalai; (179 pag.)US2019/194174; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 852227-86-2, 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. 852227-86-2 name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, 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 solution of compound 9 (56 mg, 0.12 mmol, 1.0 equiv) in anhydrous DMF (0.2 mL) was treated with 60% sodium hydride (6.0 mg, 0.15 mmol, 1.2 equiv) at room temperature. After stirring at this temperature for 5 min, 5-(chloromethyl)-l,3-dimethyl- lH-pyrazole (21 mg, 0.14 mmol, 1.1 equiv) was introduced. Then the mixture was stirred at room temperature for 1 hour. The reaction was quenched with saturated aqueous NaHCO3 solution. The resultant solution was extracted with ethyl acetate. The combined organic extracts were washed once with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on prep-TLC (ethyl acetate/dichloromethane/methanol 20:20:1, 2 runs) to afford compound 11 (27 mg, 39 %) as an oil. MS 561 (MH)+, 619 (MOAc)”, 597 (MCl37)”, 595 (MCl35)”and 559 (M-H)”. Purity >98% (HPLC).

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

Reference:
Patent; SEQUOIA PHARMACEUTICALS, INC.; WO2009/105776; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2075-45-8, 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. 2075-45-8, name is 4-Bromo-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromopyrazole (4.00 g, 27.2 mmol) in anhydrous THF(25 mL) cooled to 0 C was added NaH (60% dispersion in mineral oil, 1.63 g, 40.8 mmol) in four equivalent portions. The contents were stirred at 0 C for 30 minutes, and then 2- (trimethylsilyl)ethoxymethyl chloride (5.06 mL, 28.6 mmol) was added slowly. The reaction was stirred at room temperature for 16 hours, diluted with diethyl ether (200 mL), and washed with brine (100 mL). The organic phase was dried over anhydrous Na^SCL and concentrated under reduced pressure to afford 22 as a clear oil (7.50 g, 99% yield).1H NMR (400 MHz, CDCI3) delta 7.59 (s, 1H), 7.49 (s, 1H), 5.38 (s, 2H), 3.55 (t, J= 8.1 Hz, 2H), 0.90 (t, J= 8.5 Hz, 2H), -0.02 (s, 9H).13C NMR (101 MHz, CDCI3) delta 140.5, 129.6, 94.8, 80.8, 67.1, 17.9, -1.3.

The synthetic route of 4-Bromo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; JORGENSEN, William L.; TRIVEDI-PARMAR, Vinay; (142 pag.)WO2019/178480; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics