Day: June 7, 2021

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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, A new synthetic method of this compound is introduced below., Safety of 3-Amino-5-tert-butylpyrazole

5-tert-Butyl-2H-pyrazol-3-ylamine (1.11 g, 8.00 mmol), potassium carbonate (2.32 g, 16.8 mmol), copper (I) iodide (0.076 g, 0.40 mmol), and 3-bromo-5- methylphenol (1.80 g, 9.60 mmol) were weighed into a large microwave vial. This was then purged with argon then trans-N,N-dimethylcyclohexane-l,2-diamine (0.25 mL, 1.60 mmol) added. To this mixture was then added degassed toluene (8 mL). The mixture was then purged with argon again, the vial sealed, and heated for 1 h at 140 C in the microwave, then a further 4 h at 135 C. The mixture was cooled, diluted with ethyl acetate and passed through a pad of celite/silica, washing with more ethyl acetate. The dark solution was concentrated in vacuo. The residue was purified by FCC, using 0-40% DCM in EtOAc, to give the title compound (966 mg, 49%). NMR (300 MHz, CDC13): 1.32 (9H, s), 2.24 (3H, s), 3.82 (2H, br s), 5.49 (1H, s), 6.45-6.52 (1H, m), 6.65-6.71 (1H, m), 6.85-6.91 (lH, m).

The synthetic route of 82560-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14531-55-6, name is 3,5-Dimethyl-4-nitro-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 14531-55-6, Quality Control of 3,5-Dimethyl-4-nitro-1H-pyrazole

(0927) Step A (0928) To a solution of 3,5-dimethyl-4-nitro-1H-pyrazole (0.5 g, 3.54 mmol) in acetonitrile (10 mL), K2CO3 (1.4 g, 10.62 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Then 1-bromo-2-fluoroethane (0.67 g, 5.31 mmol) was added dropwise. The mixture was heated at reflux overnight. To the cooled reaction mixture H2O (20 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the organic layers were combined, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified on HP-Sil SNAP cartridges using a Biotage Isolera One purification system employing an EtOAc/n-heptane gradient (5/95->40/60) to afford the title compound which was used in the next step without further purification (0.515 g, 77%). (0929) 1H-NMR (400 MHz, DMSO-d6) delta=4.80 (t, 1H), 4.68 (t, 1H), 4.48 (t, 1H), 4.41 (t, 1H), 2.57 (s, 3H), 2.40 (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, 3,5-Dimethyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AC IMMUNE SA; PIRAMAL IMAGING SA; KROTH, Heiko; NAMPALLY, Sreenivasachary; MOLETTE, Jerome; GABELLIERI, Emanuele; BENDERITTER, Pascal Andre Rene; FROESTL, Wolfgang; SCHIEFERSTEIN, Hanno; MUELLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; (228 pag.)US2017/2005; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 132712-71-1, These common heterocyclic compound, 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol, 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.

General procedure: Dichloromethane (10 mL) was taken in a round-bottomed flask,into which 1.0 equivalent (1 mmol) of triethylamine and pyrazolonewere poured. The mixture was stirred for 2 min without heating. To this mixture, 1.0 equivalent of corresponding presynthesized benzylidene from malononitrile was added. Then the mixture was agitated for 25-30 min. The reaction was observed by TLC. The desired products appeared as precipitates. The precipitates were washed with water to remove the unreacted pyrazolone to obtain pure products. Melting points were recordedfor crystalline substances.

Statistics shows that 3-Methyl-1H-pyrazol-5-ol is playing an increasingly important role. we look forward to future research findings about 132712-71-1.

Reference:
Article; Kashtoh, Hamdy; Muhammad, Munira Taj; Khan, Jalaluddin J.A.; Rasheed, Saima; Khan, Ajmal; Perveen, Shahnaz; Javaid, Kulsoom; Atia-Tul-Wahab; Khan, Khalid Mohammed; Choudhary, M. Iqbal; Bioorganic Chemistry; vol. 65; (2016); p. 61 – 72;,
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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C7H13N3

A solution of Intermediate 55a (2.64 g, 6.50 mmol), 3-tert-butyl-1H-pyrazole-5-amine (997 mg, 7.1 mmol) and trans-N,N?-dimethylcyclohexane-diamine (185 mg, 0.33 mmol) was formed in toluene (25 mL). Potassium carbonate (1.9 g, 13.7 mmol) was added and the mixture degassed by bubbling nitrogen through it. Copper(I) iodide (64.0 mg, 1.30 mmol) was added and the mixture was refluxed at 110 C. for 24 h. The solvent was evaporated under reduce pressure and the residue was partitioned between EtOAc/Water and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered and evaporated. Purification by FCC eluting with a gradient of 0-50% EtOAc in cyclohexane gave the title compound (1.72 g, 64%). LCMS (Method 3): Rt 3.69 min, m/z 418 [MH+].

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; CHIESI FARMACEUTICI S.p.A.; Alcaraz, Lilian; Hurley, Christopher; Cridland, Andrew Peter; Jennings, Andrew Stephen Robert; US2014/364412; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 79080-31-2, 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. 79080-31-2 name is 1,5-Dimethyl-3-(trifluoromethyl)-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.

EXAMPLE 9 In a 100 ml of an autoclave made of Hasteroy C-276 were charged 50 ml of acetic acid, 8.2 g (50 mmole) of 1,5-dimethyl-3-trifluoromethylpyrazole, 0.249 g (1 mmole) of cobalt acetate, 0.123 g (0.5 mmole) of manganese acetate and 0.204 g (2 mmole) of sodium bromide, reaction and operation were carried out in the same manner as in Example 1. A conversion ratio of the starting 1,5-dimethyl-3-trifluoromethylpyrazole was 96.8%, and a yield of 1-methyl-3-trifluoromethylpyrazole-5-carboxylic acid was 52.0%.

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

Reference:
Patent; Nissan Chemical Industries, Ltd.; US5053517; (1991); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 2075-45-8, The chemical industry reduces the impact on the environment during synthesis 2075-45-8, name is 4-Bromo-1H-pyrazole, I believe this compound will play a more active role in future production and life.

4-bromopyrazole (15.6 g, 0.1 mol), ethyl iodide (10.9 g, 0.1 mol), tetrabutylammonium iodide (3.7 g, 0.01 mol) at room temperature,Dissolved in 5 ml of dimethyl sulfoxide (DMSO), and added with sodium hydroxide solution [sodium hydroxide solution: a solution obtained by dissolving 4.4 g (0.11 mol) of sodium hydroxide in 5 ml of water],The reaction is exothermic. After the addition is completed, it is stirred at room temperature overnight, diluted with water and diluted with dichloromethane.Drying, concentration and distillation under reduced pressure gave 16.8 g of 1-ethyl-4-bromo-1H-pyrazole.The yield was 96.0%.

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

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (16 pag.)CN108863936; (2018); A;,
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. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-pyrazol-4-amine hydrochloride

The 2,5-dichloro-N-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)pyrimidin-4-amine (430mg, 1.4046 mmol), diisopropylethylamine (546.7 mg, 4.23 mmol) and 1-methylpyrazol-4-amine hydrochloride (283.3 mg,2.12 mmol) was dissolved in n-BuOH (10 mL), the temperature of the reaction solution was raised to 150 C, sealed tube reaction for 23 hours, and then concentrated under reduced pressure.The residue was purified by silica gel column chromatography (DCM / MeOH (v / v) = 50/1) to afford the title compound as a white solid which was recrystallized from acetone to give the title compound as a white solid (220 mg, 42.6% ).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Li Xiaobo; Dai Weilong; Wang Tingjin; (74 pag.)CN104926824; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 25016-12-0,Some common heterocyclic compound, 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H8N2O, 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.

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).

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

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

Electric Literature of 578008-32-9, A common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, molecular formula is C9H15N3O2, 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.

Example 10; 3-{[4-(Azetidin-l-ylcarbonyl)phenvnoxy}-iV-(5-methyl-lH-pyrazol-3-yl)- 5- [(3S)-tetr ahydrofur an-3-yloxyl benzamide; l-Chloro-N,N,2-trimethyl-l-propenylamine (0.145 mL, 1.10 mmol) was added to a solution of 3-{ [4-(azetidin- 1 -ylcarbonyl)phenyl]oxy } -5-[(3S)-tetrahydrofuran-3- yloxy]benzoic acid (350 mg, 0.92 mmol) in DCM (6 mL) and stirred at RT for 30 – 40min. 1,1-Dimethylethyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (361 mg, 1.83 mmol) and pyridine (0.148 mL, 1.83 mmol) were added and the reaction stirred at RT for 2 hours. The solvent was removed in vacuo, water (20 mL) added and the mixture extracted with ethyl acetate (3 x 20 mL). The extracts were combined and washed with 2Nu hydrochloric acid (20 mL), a saturated solution of sodium bicarbonate (20 mL), water (20 mL), brine (20 mL), dried (MgSO4) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0- 10% methanol in DCM, to give a white solid which was taken up in acetonitrile (2 mL) and heated in a microwave reactor at 160C for 10 minutes. EPO The reaction mixture was evaporated and the residue chromatographed on silica, eluting with 0-5% methanol in DCM, to give the desired compound as a white foam (50 mg). 1H NMR delta (CDCl3): 2.11 – 2.29 (m, 2H), 2.32 (s, 3H), 2.32 – 2.40 (m, 2H), 3.88 – 4.02 (m, 4H), 4.23 (t, 2H), 4.35 (t, 2H), 4.95 – 4.99 (m, IH), 6.56 (s, IH), 6.71 (t, IH), 7.02 (d, 2H), 7.13 (s, IH), 7.21 (s, IH), 7.64 (d, 2H), 9.06 (s, IH); m/z 463 (M+H)+, 461 (M-H)’

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; WO2007/17649; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1082745-50-3, These common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, 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.

To a suspension of 0.132 g (0.63mmol) of 5-amino-l-(tetrahydro-pyran-4-yl)-l-H-pyrazole-4- carboxylic acid amide (see PCT patent application WO2010/026214) in dry EtOH (1.5mL), 0.066 g (1.66 mmol) of sodium hydride (60 % suspension in mineral oil) were added at room temperature under nitrogen. After lOmin, 0.181mg (0.945mmol) of Example 13 A were added and the reaction mixture was heated to 140C for 40 min in a microwave oven (Power 100W). The reaction mixture was then diluted with DCM, water was added, organics separated and dried over sodiumsulphate. Organics were evaporated under reduced pressure and the crude purified by flash cromatography (DCM/IPA 98:2) to obtain the title compound as a white solid. (54mg, 32%).HPLC-MS (Method lEh): R, = 8.01 minMS (APCI pos): m/z = 352 (M+H)+

Statistics shows that 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide is playing an increasingly important role. we look forward to future research findings about 1082745-50-3.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics