Day: September 29, 2021

Adding a certain compound to certain chemical reactions, such as: 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid, 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 5744-59-2, Formula: C6H8N2O2

a) Ethyl 5-(l ,5-dimethyl-lH-pyrazol-3-yl)-l ,2,4-oxadiazole-3-carboxylateEthyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), 1,5 -dimethyl- 1H- pyrazole-3-carboxylic acid (95 %, 3.78 mmol, 0.530 g) and 1,3-diisopropylcarbodi- imide (4.16 mmol, 0.525 g) were suspended in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated and pyridine was added to the residue. The resulting mixture was refluxed for 6 h and stirred at RT overnight. Pyridine was evaporated and the residue diluted with DCM and water. The phases were separated and the water phase was extracted four times with DCM. The combined organics were washed with aqueous HC1 solution, saturated NaHC03, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.285 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-c¾): delta 1.43 (t, 3H), 2.30 (s, 3H), 4.23 (s, 3H), 4.49 (q, 2H), 6.96 (s, 1H).

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

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5932-30-9, These common heterocyclic compound, 5932-30-9, name is Ethyl 5-phenyl-1H-pyrazole-3-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.

The starting material (100 mg, 0.46 mmol) was dissolved in 10 mL of acetone.Add potassium carbonate (190 mg, 1.38 mmol) and potassium iodide (8 mg, 0.046 mmol),Dimethyl sulfate (31.5 mg, 0.25 mmol), refluxing for 4 h,After TLC detects the reaction, it is filtered.The filter cake was washed with 10 mL of ethyl acetate and 10 mL of dichloromethane until no fluorescence.The filtrates were combined and concentrated.Column chromatography purification (petroleum ether: ethyl acetate = 4:1)Yellow solid99mg,Yield 93.4%,

The synthetic route of 5932-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Wang Jinxin; Yang Kan; Zhi Zhuoer; Nong Keyi; (8 pag.)CN109232426; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 718632-46-3, name is 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate, 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 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate

To a solution of 9.70 g (61.3 mmol) of 1-(trimeth- ylsilyl)cyclopropanecarboxylic acid [synthesized according to the method described in J. Org. Chem., 1982(47) 5, 893-895] in 120 ml of dehydrated dichloromethane, 6.60 ml (76.9 mmol) of oxalyl chloride and 0.25 ml (3.2 mmol) of dehydrated DMF were added in this order at 00 C. in a nitrogen atmosphere and reacted at 00 C. for 2.5 hours with stirring. After completion of the reaction, the reaction solution was concentrated under reduced pressure and dried under reduced pressure. A solution of the obtained concentration residue in 30 ml of dehydrated dichloromethane was added to a solution of 19.0 ml (109 mmol) of DIPEA and 9.94 g (30.6 mmol) of 5-tert-butyl 2-ethyl 3-amino-6,6- dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate[synthesized according to the method described in Journal of Medicinal Chemistry 2012, 55 (10), 4728-4739] in 170 ml of dehydrated dichioromethane at 00 C. in a nitrogen atmosphere and reacted at 00 C. for 24 hours with stirring. After completion of the reaction, a saturated aqueous solution of sodium bicarbonate was added to the reaction solution and stirred, followed by extraction once with dichloromethane and twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 2, silica gel, elution solvent: n-hexane:ethyl acetate=90: 10-70:30 (V/V)), and a fraction containing 5-tert-butyl 2-ethyl 6,6- dimethyl-3-[1 -(trimethylsilyl)cyclopropanecarboxamido]pyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate was concentrated under reduced pressure. The concentration residue of the fraction containing impurities was subjected again to preparative column chromatography (apparatus 2, silica gel, elution solvent: n-hexane: ethyl acetate=90: 1 0-75 :25 (V/V)), combined with the preliminarily obtained fraction, concentrated under reduced pressure, and dried under reduced pressure.

The synthetic route of 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE INDUSTRIES, LTD.; IWASE, Noriaki; AGA, Yasuhiro; USHIYAMA, Shigeru; KONO, Shigeyuki; SUNAMOTO, Hidetoshi; MATSUSHITA, Takashi; OGI, Sayaka; UMEZAKI, Satoshi; KOJIMA, Masahiro; ONUMA, Kazuhiro; SHIRAISHI, Yusuke; OKUDO, Makoto; KIMURA, Tomio; (165 pag.)US2018/186818; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 69843-13-6, 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. 69843-13-6, name is 1-Methyl-1H-pyrazol-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

4- amine (52 g, 0.53 mol, prepared according to Procedure B) and cyanamide (29 g, 0.69 mol) in dioxane (50 mL) then the mixture was heated to 95C overnight. The reaction was cooled to room temperature and the solvent removed in vacuo. The residue was washed with ether (100 mL) to afford l-(l-methyl-lH-pyrazol-4-yl)guanidine hydrochloride (93 g , ~ 100%) as a yellow solid which was used in the next step without further purification.

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

Reference:
Patent; CELLZOME LIMITED; ELLARD, Katie; MAJOR, Jeremy; JONES, Alison; LYNCH, Rosemary; RAMSDEN, Nigel; WO2012/62704; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, 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 5334-40-7, HPLC of Formula: C4H3N3O4

A mixture of 4-nitro-3-pyrazolecarboxylic acid (4.98 g, 31.7 mmol), trans 4-aminocyclohexanol (3.65 g, 31.7 mmol), EDAC (6.68 g, 34.8 mmol) and HOBt (4.7 g, 34.8 mmol) in DMF (120 ml) was stirred at ambient temperature for 16 hours. The mixture was reduced in vacuo, the residue taken up in CH2CI2 and washed successively with 5percent citric acid, saturated aqueous sodium bicarbonate, water and brine. The product was found to be mainly in the citric acid wash, which was basified and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to give a white solid, which was triturated with CHCI3 to give 1.95 g of 4-nitro-1H-pyrazole-3-carboxylic acid 4-hydroxy-cyclohexylamide. (LC/MS: Rt 1.62, [M+H]+255).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Nitro-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77428; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 28466-26-4, These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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.

As shown in step 5-i of Scheme 5, methyl 4-bromo-2-(bromomethyl)benzoate (Compound 2018, 2.08 g, 6.75 mmol; prepared by reacting l-(4-bromo-2- methylphenyl)ethanone with NBS),lH-pyrazol-4-amine (561 mg, 6.75 mmol), and DIEA (873 mg, 1.18 mL, 6.75 mmol) were combined in DMF (7.78 mL) and heated at 110 C for 90 min. The reaction mixture was diluted with MeOH (60 mL) and the resulting white crystaline solid was collected by filtration and dried under vacuum to give 5-bromo-2-(lH- pyrazol-4-yl)isoindolin-l-one (Compound 2019, 1.21 g, 4.35 mmol, 64% yield): ESMS (Mu+Eta) 279.99

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 26621-44-3, A common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

Under inert gas (eg high purity nitrogen) protection to 10 mlSchlek reaction tube was added 0.02 mmol of water-soluble palladium on water-bound monophosphine salt compound (18), 1.0 mmol of 4-methoxy-2-chloropyridine, 1.5 mmol of 3-nitropyrazole, 3 mmol of potassium carbonate and 5 ml of Water, the reaction tube was replaced with nitrogen three times, and then heated to 100 C with an oil bath under magnetic stirring, and the reaction was refluxed for 24 hours. The oil bath was removed and the reaction was concentrated with a rotary evaporator. The residue was chromatographed on silica gel using ethyl acetate as the developing solvent to give pure product 4-methoxy-2-pyridine-3-nitroPyrazole in 85% yield.

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luoyang Normal College; Li Hongmei; Xu Chen; Tu Tianyong; Wang Zhiqiang; Hao Xinqi; (10 pag.)CN106674287; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 129768-30-5 as follows. category: pyrazoles-derivatives

Example 11; N-(2-ethoxybenzyl)-1-(1-(2-(methylamino)ethyl)piperidin-4-yl)-3-(trifluoromethyl)-1 H-pyrazole-5-carboxamide (98); Step 1 tert-butyl 4-(5-(ethoxycarbonyl)-3-(trifluoromethyl)-1 H-pyrazol-1-yl)piperidine-1- carboxylate (93); [0268] tert-Butyl 4-iodopiperidine-i-carboxylate (5 683, 18 26 mmol, E G Corley et al, JOC, 2004, 69, 5120-5123) in DMF (30 7 ml) was added to a mixture of ethyl 3- (trifluoromethyl)-1 H-pyrazole-5-carboxylate (3 2 g, 15 37 mmol, M -A Plancquaert et al, Tetrahedron, 52, 4383-4396) and potassium carbonate 95 31 g, 38 4 mmol) and the mixture was stirred at 80oC for 16h After cooling, water was added and the mixture was extracted with EtOAc, and the organic extraxts were dried, filtered and concentrated Chromatographic purification of the residue by Biotage (5-20% EtOAc m Hexanes, 25M column) gave compound 93 as colorless oil (2 4 g, 39 9% yield) LFRMS (ESI) calc 391 4, found 414 1 (M+Na)+

According to the analysis of related databases, 129768-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; METHYLGENE INC.; WO2008/104077; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 152120-54-2, These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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: Method B. The required amine hydrochloride salt 7 (1.5-6.0 equiv) and pyrazole-1-carboxamide 6a (1.0 equiv) were dissolved in acetonitrile or chloroform (ca. 1 mL per mmol) and triethylamine (twofold excess based on 7) was added drop-wise with stirring, together with anhydrous MgSO4 to dryness. After 16 h the mixture was filtered, evaporated and purified by column chromatography on silica.

The synthetic route of 152120-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Al Shuhaib, Zainab; Davies, Deiniol H.; Dennis, Mark; Evans, Daniel M.; Fletcher, Matthew D.; Franken, Herjan; Hancock, Paul; Hollinshead, Jackie; Jones, Iestyn; Kaehm, Kristina; Murphy, Patrick J.; Nash, Robert; Potter, David; Rowles, Richard; Tetrahedron; vol. 70; 29; (2014); p. 4412 – 4419;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3-methyl-4-nitro-lH-pyrazole (1 -1, 398 nig, 3.13 mmol) in DMF (10 niL) was added NaH (125 mg, 3.13 mmol, 60% purity) at 0 C, then the reaction was stirred at 20 C for 1 h. Then, (3-methyl- 5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridin-6-yl) methanesulfonate (604 mg, 2.61 mmol, 70% purity) in DMF (4 mL) was added to the solution at 20 C. Then, the mixture was stirred at 80 C for 12 h. The reaction solution was added with NH4Q solution (20 ml,), extracted with DCM:MeOH (20 mL chi 3, ratio=3: l). The organic layers were combined, dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by prep-TLC (DCM:MeOH = 5: 1) to give a mixture of 3-niethy3~6~(3-methyi-4~nitro^ and 3- methyl-6-(5~methyl-4-nitro-pyra^ as a yellow gum. LCMS: RT 0.925 min, m/z = 263.1 | M – H j ‘ . NMR (400 MHz, CDC13): delta 8.25 (s, 0.6 H), 8.13 (s, 0.3 H), 4.68 – 4.81 (m, 1 H), 4.14 – 4.42 (m, 2 H), 3.02 – 3.31 (m, 2 H), 2.77 (s, 1 H), 2.55 (s, 2 H), 2.44 – 2.53 (m, 4 H), 2.43 (s, 1 1H 1).

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

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics