Tag: M.W:100-200

Application of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

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-Amino-1-phenyl-1H-pyrazol-5(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 17635-45-9, 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. 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred suspension of thioacid (1.0 mmol) in THF (5 mL) were added I2 (0.6 mmol, 152 mg), DIPEA (1.2 mmol, 0.156 mL) and HOBt (2.0 mmol, 270 mg) at r.t., followed by the appropriate amine(1.1 mmol). The reaction mixture was stirred for 0.5 to 1 h as analyzed by TLC (until complete disappearance of the thioacid was observed). After the reaction was complete, the solvent was evaporated under vacuum and diluted with EtOAc (20 mL). The organic phase was washed with 10percent HCl (2 × 10 mL), 1 N Na2CO3(3 × 10 mL), H2O (2 × 10 mL) and brine (10 mL) and then dried over anhydrous Na2SO4. The solvent was filtered and evaporated under reduced pressure. The crude reaction mixture was purified under column chromatography using hexane?EtOAc (7:3) as the eluentto afford the desired product.

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-Pyrazol-1-yl-phenylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Madhu, Chilakapati; Vishwanatha; Sureshbabu, Vommina V.; Synthesis; vol. 45; 19; (2013); p. 2727 – 2736;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 151049-87-5, name is 3-Bromo-1-methyl-1H-pyrazole, molecular formula is C4H5BrN2, 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. Formula: C4H5BrN2

Example 0930 0930-1 3-Methoxyazetidine hydrochloride (160 mg), sodium tert-butoxide (250 mg), 1,4-dioxane (10 mL), and ((2-dicyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl))palladium(II) methanesulfonate (BRETTPHOS-PD-G3 (trade name, manufactured by Sigma-Aldrich Co. LLC.)) (40 mg) were added to 3-bromo-1-methyl-1H-pyrazole (160 mg), followed by stirring at 80 C. for 2 hours. The reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining 3-(3-methoxyazetidin-1-yl)-1-methyl-1H-pyrazole (41 mg) as yellow oily substance. MS m/z (M+H): 168.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 151049-87-5, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3994-50-1, name is 1-Methyl-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 3994-50-1, Recommanded Product: 3994-50-1

A mixture of a portion (0.7 g) of the material so obtained, platinum oxide (0.05 g), ethyl acetate (5 ml) and ethanol (15 ml) was stirred under 3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material (0.6 g); 1H NMR: (DMSOd6) 3.64 (s, 3H), 6.86 (s, IH), 6.97 (s, IH).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/40520; (2006); 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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

PREPARATION EXAMPLES Preparation of compound No. 3 At room temperature, 70 mul (0.8 mmol) of oxal chloride and 30 mul of dimethylformamide are added to a suspension consisting of 130.0 mg (0.7 mmol) of 3-(difluoromethyl)-1-methyl-1H-pyrazol-4-carboxylic acid in 5 ml of dichloromethane. After 2 hours, this reaction mixture is added dropwise to a solution consisting of 160.0 mg (0.7 mmol) of N-cyclopropyl-2-(1,3-dimethylbutyl)aniline and 130 mul (1.0 mmol) of triethylamine in 5 ml of dichloromethane. After 48 hours of stirring at room temperature, 4 ml of water are added and the organic phase is separated off, dried over magnesium sulphate and concentrated under reduced pressure. This gives, after column chromatography (gradient cyclohexane/ethyl acetate), 202.0 mg (0.5 mmol, 72% of theory) of N-cyclopropyl-3-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazol-4-carboxamide [log P (pH 2.3) 3.89].

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer CropScience AG; US2009/176844; (2009); 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. 33064-36-7, name is 1H-Pyrazole-3-carboxamide, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

A mixture of feri-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (200 mg, 0.45 mmol), lH-pyrazole-3-carboxamide (124 mg, 1.12 mmol), tripotassium phosphate (133 mg, 0.63 mmol), [(2-di-ieri-butylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-l, – biphenyl)-2-(2 ‘-amino- l,l’-biphenyl)]palladium(II) methanesulfonate (= tBuBrettPhos Pd G3) (23 mg, 0.027 mmol), 2-(di-ieri-butylphosphino)-2′,4′,6′- triisopropyl-3,6-dimethoxy-l,l ‘-biphenyl (= tBuBrettPhos) (13 mg, 0.027 mmol) was added to a flask and flushed with argon before being suspended in 2 ml of ieri-butanol. Argon was bubbled for Imin more through the suspension, which was then stirred overnight at 110 C. After cooling to RT, the mixture was filtered and purified by preparative HPLC (gradient acetonitrile/water with 0.1 % trifluoroacetic acid). Evaporation of the combined product fractions yielded the title compound (119 mg, 56% of theory). LC-MS (Method 2): Rt = 2.73 min, MS (ESINeg): m/z = 476 [M-H]”

The synthetic route of 33064-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUSS, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; (308 pag.)WO2016/173948; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, 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 82560-12-1, Computed Properties of C7H13N3

To a solution of methyl-4-iodo-2-methoxybenzoate (10.0 g, 34.2 mmol) in toluene (90 mL) was added 3-tert-butyl-1H-pyrazol-5-amine (5.24 g, 37.7 mmol) followed by (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (870 mg, 1.08 mL, 6.85 mmol) and potassium carbonate (14.9 g, 108 mmol). The mixture was purged with N2, copper(I) iodide (326 mg, 1.71 mmol) was added and the reaction mixture was heated at reflux under N2 for 18 hr. The mixture was cooled to RT and was partitioned between EtOAc (100 mL) and water (3×150 mL). The organic layer was separated and washed with aq. citric acid solution (1% w/v, 150 mL) followed by water (150 mL), and was then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 330 g, EtOAc in isohexane, 0-100%, gradient elution) to afford methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)-2-methoxybenzoate as a buff coloured solid (3.62 g, 35%); Rt 1.93 min (Method 2); m/z 304 (M+H)+ (ES+).

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; King-Underwood, John; Hardy, George; Murray, Peter John; Williams, Jonathan Gareth; Onions, Stuart Thomas; US2013/29990; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-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.

To a solution of 2,4-difluoro-5-nitrobenzonitrile (Method 9, 5.0 g, 27 mmol) and DIEA (5.4 ml, 31 mmol) in THF (20 ml) was added dropwise the solution of 5-cyclopropyl- 1H-pyrazol-3-amine (3.2 g, 26 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 1 hr. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 3 : 1) to give the title compound as a yellow solid (5.5 g, 74%). NMR (400 MHz) 12.54 (s, 1H), 10.13 (s, 1H), 8.78 (d, J= 7.2 Hz, 1H), 8.10 (d, J= 13.6 Hz, 1H), 6.02 (s, 1H), 1.91 (m, 1H), 0.97 (m, 2H), 0.72 (m, 2H). MS: Calcd. : 287; Found: [M+H]+ 288.

Statistics shows that 5-Cyclopropyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 175137-46-9.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route 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

Electric Literature of 175137-46-9, A common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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 solution of 2,3,6-trichloro-5-nitropyridine (1.62 g, 7.10 mmol) and DIEA (1.24 ml, 7.1 mmol) in THF (25 ml) was added dropwise a solution of 5-cyclopropyl-lH-pyrazol-3- amine (0.70 g, 5.68 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 24 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 1.5 : 1) to give the title compound as a yellow solid (0.83 g, 47%). NMR (400 MHz) 12.39 (s, IH), 10.12 (s, IH), 8.77 (d, J= 1.2 Hz, IH), 6.35 (s, IH), 1.95 (m, IH), 0.96 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 313; Found: [M+H]+ 314

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; WO2006/82392; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics