Tag: M.W:100-200

Reference of 143426-49-7, A common heterocyclic compound, 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol, molecular formula is C10H10N2O, 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 stirred solution of 4-(1 H-pyrazol-1 -yl)phenyl)methanol (0.2 g, 1.14 mmol) in DCM (10 mL), SOCI2 (0.2 mL, 2.29 mmol) was added at 0 C and the reaction mixture was stirred for 2 h. After completion of reaction, the reaction mixture was concentrated under vacuum and co-distilled with DCM to get the title compound. It was used in the next step without further purification. Yield: (0.170 g, brown gummy solid). LCMS: (Method A) 193.1 (M+H), Rt. 3.46 min, 94.32% (Max).

The synthetic route of 143426-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; RAKESH, Paul; (338 pag.)WO2020/39027; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 423768-52-9,Some common heterocyclic compound, 423768-52-9, name is 3-(Aminomethyl)-1,5-dimethylpyrazole, molecular formula is C6H11N3, 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 ethyl 2-(2-amino-4,6-dichloropyrimidin-5-yl)acetate (200 mg, 0.80 mmol) in EtOH (30 mL) was added (l,5-dimethyl-lH-pyrazol-3-yl)methanamine (300 mg, 2.40 mmol) and Et3N (400 mg, 3.96 mmol). The resulting solution was refluxed for 3 hours. The reaction mixture was concentrated under vacuum. The residue was purified on a silica gel column with DCMrMeOH (50:1), resulted in 0.25 g (31%) of ethyl 2-(2-amino-4-chloro- 6-((l,5-dimethyl-lH-pyrazol-3-yl) methylamino)pyrimidin-5-yl)acetate as a yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Aminomethyl)-1,5-dimethylpyrazole, its application will become more common.

Reference:
Patent; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 920006-32-2,Some common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, molecular formula is C7H10N2O2, 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.

A mixture of 2-isopropylpyrazole-3-carboxylic acid (50 mg, 291.89 mumol, 1 eq), 2-methyl-4-[(E)-2-(o-tolyl) vinyl]aniline (93.12 mg, 291.89 mumol, 1 eq), T3P (1.86 g, 2.92 mmol, 1.74 mL, 50%, 10 eq) in pyridine (5 mL) was stirred at 60 C. for 2 h. The mixture was concentrated under reduced pressure to give a residue which was purified by preparative HPLC (column: Phenomenex Gemini 150*25 mm*10 um; mobile phase: [water(0.05% HCl)-ACN]; B %: 55%-85%, 10 min). The mixture was lyophilized, purified by preparative TLC (SiO2, PE/EtOAc=5/1, Rf=0.57) to give 2-isopropyl-N-[2-methyl-4-[(E)-2-(o-tolyl)vinyl]phenyl]pyrazole-3-carboxamide (compound I-42, 18.26 mg, 48.58 mumol, 16.6% yield, 95.6% purity) as an off-white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.95 (d, J=8.0 Hz, 1H), 7.60-7.55 (m, 3H), 7.40-7.39 (m, 2H), 7.30 (d, J=16.0 Hz, 1H), 7.19-7.17 (m, 3H), 6.96 (d, J=16.0 Hz, 1H), 6.61 (s, 1H), 5.57-5.47 (m, 1H), 2.44 (s, 3H), 2.35 (s, 3H), 1.54 (d, J=6.8 Hz, 6H); ES-LCMS m/z 360.2 [M+H]+.

The synthetic route of 920006-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (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. 15803-02-8, name is 4-Bromo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H5BrN2

A. Synthesis of 1-(1-methyl-1H-pyrazol-4-yl)ethanone 4-Bromo-1-methyl-1H-pyrazole (41.3 mL, 400 mmol), was dissolved in tetrahydrofuran (750 mL) and cooled to -78 C. N-Butyllithium (2.5 M solution in hexanes, 160 mL, 400 mmol) was added drop-wise over 30 minutes, and the resulting mixture was stirred for 1 hour at -78 C. After drop-wise addition of a solution of N-methoxy-N-methylacetamide (40.9 mL, 400 mmol) in tetrahydrofuran (100 mL) to the -78 C. reaction mixture, the cooling bath was allowed to warm to 0 C. over 4 hours. The reaction was then quenched with saturated aqueous sodium chloride solution (50 mL), and volatiles were removed in vacuo. The residue was diluted with ethyl acetate (1000 mL), treated with magnesium sulfate, and stirred for 30 minutes before being filtered and concentrated in vacuo. Purification was carried out via silica gel chromatography (material was loaded in a minimum amount of dichloromethane; Gradient: 5% to 100% ethyl acetate in heptane) to provide a pale yellow oil that solidified on standing. Yield: 28.5 g, 230 mmol, 57%. 1H NMR (500 MHz, CDCl3) delta 2.37 (s, 3H), 3.90 (s, 3H), 7.83 (s, 1H), 7.84 (s, 1H).

The synthetic route of 15803-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2012/214791; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 2654-57-1, 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. 2654-57-1, name is 4-Methyl-1-phenylpyrazolidin-3-one belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(a) 3-hydroxy-4-methyl-1-(4-nitro-phenyl)-1H-pyrazole 8.00 g (45.4 mmol) 4-methyl-1-phenyl-1H-pyrazolidin-3-one are added to 80 ml conc. sulphuric acid at -5 C. with stirring and stirred for another 5 min. Then 3.8 ml (54.5 mmol) 65% nitric acid are added with cooling such that the temperature remains between -15 and -10 C. The reaction mixture is stirred for 1 h between -20 and -5 C., then poured into ice water and suction filtered. The filter cake is washed with water, dried at 55 C. and further reacted without any further purification. Yield: 8.00 g (approx. 40%), approx. 50% C10H9N3O3 (219.20) Rf value: 0.70 (silica gel; cyclohexane/ethyl acetate=1:1)

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, 4-Methyl-1-phenylpyrazolidin-3-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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. Computed Properties of C6H5F3N2O2

Reference Example 3A mixture of 0.19 g of 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carboxylic acid, 0.15 g of thionyl chloride and 5 mL of hexane was heated to reflux for 2 hours. The reaction mixture was concentrated under reduced pressure to obtain 0.14 g of 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride. To a mixture of 0.22 g of N-(2-aminobenzoyl)-N’-ethoxycarbonylhydrazine and 10 mL of pyridine was added 0.14 g of the resulting 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride, and the mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and a formed precipitate was collected by filtration to obtain 0.23 g of a compound I-(3). 1H-NMR (DMSO-d6, TMS) delta(ppm): 1.20 (3H, t, J=8 Hz), 4.10 (2H, q, J=8 Hz), 4.19 (3H, s), 7.17 (1H, s), 7.28 (1H, t, J=8 Hz), 7.60 (1H, t, J=8 Hz), 7.79 (1H, d, J=8 Hz), 8.37 (1H, d, J=8 Hz), 9.02 (1H, brs), 10.41 (1H, brs), 11.50 (1H, brs)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 128694-63-3, its application will become more common.

Reference:
Patent; Natsuhara, Katsuya; Nishimura, Shinya; US2010/99692; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 947763-34-0, 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. 947763-34-0, name is 1-Ethyl-3-methyl-1H-pyrazol-4-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 1-ethyl-3-methyl-1H-pyrazol-4-ylamine (1.345 g, 10.75 mmol, commercially available) and (6-trifluoromethyl-pyridin-3-yl)-acetonitrile (distilled 166-175 C./2 mb, 1.0 g, 5.4 mmol) in MeOH (10 mL) was treated with HCO2NH4 (1.694 g, 26.86 mmol) and 10% Pd/C (200 mg) and stirred at 80 for 1.5 h. Filtration, concentration and purification by HPLC afforded the title compound (0.213 g, 13%) as a light brown oil. MS m/e: 299.3 [M+H]+.

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-Ethyl-3-methyl-1H-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark; US2009/312314; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 19959-77-4, name is 2-(5-Methyl-1H-pyrazol-3-yl)pyridine, 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. Application In Synthesis of 2-(5-Methyl-1H-pyrazol-3-yl)pyridine

Complex 3 could be obtained by two methods:Method 1: using the diffusion method as for the above mentionedcompounds; solid HL (14.5 mg, 0.10 mmol) and Cu(CH3-COO)2H2O (19.9 mg, 0.10 mmol) were separated into two armsof an H-tube, which was filled with acetonitrile as the solvent system.Two weeks later, black-green block crystals of compound 3were obtained.Method 2: using the solvothermal method; HL (15.9 mg,0.10 mmol) and Cu(CH3COO)2H2O (19.9 mg, 0.10 mmol) were dissolvedin acetone (10 mL), to which NEt3 (14 muL, 0.1 mmol) wasadded dropwise under stirring. The resultant green solution wascontinuously stirred for an additional 10 min, then transferred intoa 25 mL Teflon-lined autoclave and heated at 140 C for 3 days. Theresultant clear solution was filtered, then left to evaporate for threedays to give black-green block crystals of 3. The crystals werewashed with n-hexane 2 3 times, then dried in a vacuum. Yield:26.9 mg (48%), M.p. >300 C. Anal. Calc. for C22H22N6O4Cu2 (FW,561.54): C, 47.06; H, 3.95; N, 14.97. Found: C, 47.34; H, 3.89; N,14.71%. Selected IR data (cm-1, KBr): 3422 (br); 2926 (w); 1611(s) (m(CN)); 1584 (s) (m(CC)); 1497 (w); 1462 (s) (d(CH3));1391 (w); 1335 (s); 1184 (w); 1050 (w); 988 (w); 779 (s); 749(w); 683 (m); 620 (w) (see Scheme 2).

The synthetic route of 2-(5-Methyl-1H-pyrazol-3-yl)pyridine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Feng-Lei; Zhu, Guang-Zhou; Liang, Bei-Bei; Shi, Yan-Hui; Li, Xiu-Ling; Polyhedron; vol. 128; (2017); p. 104 – 111;,
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. 19959-77-4, name is 2-(5-Methyl-1H-pyrazol-3-yl)pyridine, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(5-Methyl-1H-pyrazol-3-yl)pyridine

A 5mL ethanol solution of L (0.2mmol, 15.9mg) and Et3N (0.1mmol, 14mul) was mixed with a 5mL ethanol solution of ZnCl2 (0.1mmol, 13.6mg), and the resulting mixture was then stirred for 15min to obtain a colorless solution. This colorless solution was filtered and left to evaporate for three days, giving rise to colorless rod-like crystals. The resulting crystals were washed with n-hexane 2?3 times, then dried in vacuum. Yield: 23.6mg (80%), M. p. >300C. Anal. Calc. for C9H9Cl2N3Zn (FW, 295.46): C, 36.58; H, 3.07; N, 14.22. Found: C, 36.08; H, 3.53; N, 13.79%. Selected IR data (KBr, cm-1): 3175(s), 3133 (s), 3109 (m), 3087 (m), 2924 (s), 2853 (s), 1611 (m) (nu(C=N)), 1573 (m) (delta(C=C)), 1446 (s) (nu(CH3)), 1303 (m) (nu(C-N)), 1261 (w), 1114 (w), 1053 (w), 1023(w), 988 (s), 823 (m), 793 (s), 738 (m).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 19959-77-4.

Reference:
Article; Zhu, Guang-Zhou; Xing, Bei-Bei; Yang, Feng-Lei; Li, Xiu-Ling; Polyhedron; vol. 81; (2014); p. 705 – 714;,
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. 796729-03-8, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid

Add 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid (1.60 g, 10.5 mmol) and 30 mL of 1,4-dioxane, benzyl alcohol to a 50 mL vial (1.64 mL, 15.8 mmol), DIPEA (3.5 mL, 21.0 mmol),And DPPA (4.35g, 15.8mmol), reacted at 105 C for 3h, the reaction was completed by TLC, directly spin-drying silica gel column chromatography, eluting with PE / EA = 2 / 1 to obtain 0.35g white solid, yield 13 %,

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.; Lin Xinglong; Xie Hongming; Hu Yangxiao; Li Shiguang; Zhang Yingjun; Tan Yumei; Yuan Mingyun; (124 pag.)CN108948019; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics