Tag: M.W:100-200

Electric Literature of 83725-05-7, 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 83725-05-7 as follows.

A mixture of N-(5-methyl-1H-pyrazol-3-yl)acetamide (1.448 g, 10.4 mmol),1 3,4-dihydro-2H-pyran (2.39 mL, 26.0 mmol) and trifluoroacetic acid (15 muL, 0.208 mmol) in anhydrous MeCN (15 mL) was refluxed for 2 h. Solvent was evaporated and the residue was resuspended in CH2Cl2 (50 mL) and washed with H2O and brine. After drying with Na2SO4, solvent evaporation and silica gel column chromatography (PE-EtOAc, 6:4) N-(5-Methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)acetamide (1.87 g, quantitative) was obtained. 1Lu, Y.; Kraatz, H.-B. Inorg. Chim. Acta 2004, 357, 159-1661H NMR (400 MHz, CDCl3): =7.61 (bs, 1H), 6.50 (s, 1H), 5.15 (dd, J=10.0 Hz, J=2.4 Hz, 1H), 4.05 (d, J=11.4 Hz, 1H), 3.63 (dt, J=11.8 Hz, J=2.5 Hz, 1H), 2.31 (s, 3H), 2.30 (m, 1H), 2.09 (s, 3H), 2.06 (m, 1H), 1.86 (d, J=11.0 Hz, 1H), 1.63-1.67 (m, 3H).MS (ESI): m/z=224.37 [MH+].

According to the analysis of related databases, 83725-05-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AC IMMUNE SA; US2010/144793; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5203-77-0, A common heterocyclic compound, 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, molecular formula is C5H8N2O, 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: Intermediate 7 (4mmol), dissolved in dry dichloromethane (60mL), and PCl5 (4.2mmol) were added and stirred at room temperature for 1h. The solvent was moved out under reduced pressure to afford acid chloride, the acid chloride was then dissolved in dry CH2Cl2 (60mL), Then 1-methyl-1H-pyrazol-5-ol (4mmol) and Et3N (4.8mmol) were added to the above solution, and stirred for a further 18-24hat room temperature. After adding dichloromethane (30mL), the resultant mixture was washed sequentially with 2N hydrochloric acid (100mL), saturated NaHCO3 and saturated NaCl and dried over Na2SO4. The rest of the solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V:V = 1:2) to obtain the desired intermediate 8 as a write powder (30%-70%). 4.1.10 1-methyl-1H-pyrazol-5-yl3-methyl-2-oxo-1-propyl-2,3-dihydro-1H-benzo[d] imidazole- 5-carboxylate Yield: 45%. m.p. 107-108C. 1H NMR (600MHz, CDCl3) delta 8.01 (dd, J=8.4, 1.2Hz, 1H), 7.77 (d, J=1.2Hz, 1H), 7.48 (d, J=1.8Hz, 1H), 7.10 (d, J=8.4Hz, 1H), 6.20 (d, J=1.8Hz, 1H), 3.92 (t, J=7.2Hz, 2H), 3.80 (s, 3H), 3.51 (s, 3H), 1.91-1.71 (m, 2H), 1.00 (t, J=7.8Hz, 3H). EI-MS (m/z): 314.18 (M)+.

The synthetic route of 5203-77-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Yu-Ling; Lin, Hong-Yan; Ruan, Xu; Yang, Sheng-Gang; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 427 – 438;,
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5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3-Methyl-4-nitro-1H-pyrazole

DIAD (930 muIota_, 4.7 mmol) was added to a solution of 3-methyl-4-nitro-1 H-pyrazole (500 mg, 3.93 mmol), /V-methyl-4-piperidinol (453 mg, 3.93 mmol) and triphenylphosphine (1238 mg, 4.7 mmol) in THF (25ml_). The reaction mixture was stirred at rt for 5 days. The mixture was cone, in vacuo before purification by flash chromatography on silica, washing with 50% EtOAc/DCM, followed by 5/45/50 MeOH/EtOAc/DCM mixture. The product was eluted with 2/5/43/50 NEt3/MeOH/EtOAc/DCM mixture to give the title compound as an off-white low melting solid (202 mg, 23%). LCMS (Method 1 ) Rt 2.7 min, ESIMS m/z [M+H]+ 225.3.

The synthetic route of 5334-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIONOMICS LIMITED; HARVEY, Andrew John; RIPPER, Justin Anthony; HUFF, Belinda Cheryl; PAUL, Dharam; WO2015/123722; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 25016-20-0, A common heterocyclic compound, 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, molecular formula is C5H6N2O2, 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.

i-Methyl-I H-pyrazole-3-carboxylic acid (48.8 mg) was dissolved in a solution of DMF (3 ml_), DIPEA (182 mul_) and HATU (201 mg), the reaction was stirred at room temperature for 15 mins. Intermediate 64 (150 mg) in DMF (1 ml.) was added and the reactions were stirred at 5O0C under nitrogen for 22 h. The reaction mixture was evaporated in vacuo and was partitioned between DCM and saturated sodium bicarbonate solution. The organic phase was collected and dried by passing through a hydrophobic frit and evaporated in vacuo. The crude material was purified using a 12 g silica ISCO cartridge eluting with a gradient of 5 – 100% EtOAc in cyclohexane to give the title compound. MS calcd for (C29H34N4O4S + H)+ : 535 MS found (electrospray) : (M+H)+ = 535

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; SMITHKLINE BEECHAM CORPORATION; WO2008/59042; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 25016-11-9, 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Example 12: l-{l-[9-Methyl-8-(l-methyl-lH-pyrazol-4-yI)-9H-purin-6-yI]piperidin-4- yI}-l,3-dihydro-2H-benzimidazol-2-one (Compound 149)l H9-Methy -8-a-methyl-lH-pyrazol-^2H-benzimidazol-2-one[00207] To a solution of l-(l-(5-amino-6-(methylamino)pyrimidin-4-yl)piperidin-4-yl)- lH-benzo[d]imidazol-2(3H)-one (70 mg, 0.2 mmol) in anhydrous ethanol (8 mL) were added 1 -methyl- lH-pyrazole-4-carbaldehyde (34 mg, 0.3 mmol) and catalytic amount of hydrochloric acid (0.05 mL, 4M HCl in Dioxane, Aldrich). The reaction mixture was heated to 80 C for 18 hours. The resulting precipitate was collected by vacuum filtration, washed with ethanol (2 mL) and dried under reduced pressure, to give 62.6 mg (70% yield) of the title compound. NMR (400MHz, DMSO-d6): delta 10.84 (s, 1H), 8.41 (s, 1H), 8.25 (s, 1H), 8.02 (s, 1H), 7.13 (dd, 1H), 6.93 (m, 3H), 4.53 (m, 1H), 3.92 (s, 3H), 3.81 (d, 3H), 3.33 (m, 2H), 3.24 (m, 2H), 2.33 (m, 2H), 1.82 (d, 2H); MS (EI) for C22H23N9O: 430.4 (MH+).

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

Reference:
Patent; EXELIXIS, INC.; PATRICK, Kearney; WO2012/37226; (2012); 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. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate

2-(2-Chloro-4-trifluoromethyl-phenyl)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one: 4-Bromo-2-(2-chloro-4-trifluoromethyl-phenyl)-2H-phthalazin-1-one (obtained from the above phthalazine-1,4-dione by bromination with POBr3 in analogy to Method R, as reported above) (0.15 g, 0.37 mmol), 3-amino-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.080 g, 0.41 mmol), Cs2CO3 (0.033 g, 0.34 mmol), tris-(dibenzylideneacetone)-dipalladium (0.017 g, 0.01 9 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.022 g, 0.037 mmol) in 2 ml dry dioxane under nitrogen were heated to 100 C. for 18 hours, and then allowed to cool to RT. H2O was added and the solvent was evaporated in vacuum. The resulting solid was collected by filtration. Purification of the raw product by preparative HPLC gave the title compound (0.069 g, 44% yield). 1H-NMR: (400 MHz, D6-DMSO) 11.92 (1H, s), 9.34 (1H, s), 8.54 (1H, d), 8.35 (1H, d), 8.14 (1H, s), 8.01 (1H, t), 7.92 (3H, m), 6.06 (1H, s), 2.14 (3H, s); MS (ESI+)=420.23 (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; Roche Palo Alto LLC; US2007/219195; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 4522-35-4, 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. 4522-35-4, name is 3-Iodo-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(1) a nitrogen gas atmosphere, in tetrahydrofuran (16 mL) solution of 3-iodo -1H- pyrazole (1.55 g), sodium hydride at 0 C. (purity 55%, 384 mg) and stirred for 15 minutes added.There was added dropwise a tetrahydrofuran solution (10 mL) of ethyl bromoacetate (1.06 mL), and stirred for 3 hours. Under ice-cooling, and extracted with chloroform by the addition of 1M hydrochloric acid to the reaction mixture. Organic layer was dried over anhydrous magnesium sulfate, and after filtration, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 100: 0 ? 70: 30) to give the (3-iodo -1H- pyrazol-1-yl) colorless oil Ethyl acetate (1.64 g) It was obtained as a material.

The synthetic route of 3-Iodo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
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Pyrazoles – an overview | ScienceDirect Topics

Reference of 368870-03-5, These common heterocyclic compound, 368870-03-5, name is (4-(1H-Pyrazol-1-yl)phenyl)methanamine, 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.

5 mmol of compound III was dissolved in 20 mL of N, N-dimethylacetamide (DMA),20 mmol of N, N-diisopropylethylamine (DIPEA) was then added.6 mmol of intermediate IIb was added thereto at room temperature. Gabi,The temperature was raised to 90 C for 22 hours.Stop the reaction, remove the solvent under reduced pressure,The obtained crude product was separated by column chromatography to obtain the target compound Ib.

The synthetic route of 368870-03-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nantong University; Dai Hong; Liang Kai; Ni Yadan; Li Jinfeng; Shi Yujun; Gao Lei; Sui Ying; Zhou Huanyu; Zhou Qian; Yan Ruijian; (7 pag.)CN110713460; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 34605-66-8, name is 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole, molecular formula is C10H13N3, 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 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole

A stirred solution of 3-(2,5-dimethylpyrrol-1-yl)-1-methyl-pyrazole (2.000g, 11 .4lmmol) intetrahydrofuran (l5mL) was cooled to -78C under an atmosphere of nitrogen. Butyllithium (1.6mol in hexanes)(7.8mL, 12.SSmmol) was then added over l5mins. The resulting solution was stirred at -78C for 2 hours. 1-bromo-3-methyl-but-2-ene (1.701g, 11 .4lmmol) dissolved in THE (5mL) was then added over 1 Omins, maintaining a temperature below -60C. The reaction mixture was stirred cold for a further 10 minutes and then allowed to warm slowly to ambienttemperature over a period of 1 hour. Saturated aqueous ammonium chloride was added to quench the reaction. Ethyl acetate was then added and the layers separated. The aqueous layer was extracted three times with ethyl acetate. The combined organics washed with water, dried over Mg504 and concentrated in vacuo to brown oil. Chromatography on silica gel gave yellow oil 1.728g (62%). 1H NMR (CDCI3) 5.90 (s, 1H), 5.83 (s, 2H), 5.30-5.25 (m, 1H), 3.79 (s, 3H),3.36-3.32(m, 2H), 2.11 (s, 6H), 1.78(s, 3H), 1.73(s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34605-66-8, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; BOEHMER, Jutta Elisabeth; PHADTE, Mangala; LONGSTAFF, Adrian; MORRIS, James Alan; DESSON, Timothy Robert; HOTSON, Matthew Brian; DOWLING, Alan John; WHITTINGHAM, William Guy; DALENCON, Anne Jacqueline; DE FRAINE, Paul John; THOMPSON, Alison Jane; HACHISU, Shuji; WO2015/18433; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, 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. name: 3-Amino-5-tert-butylpyrazole

3-Tert-butyl-1 H-pyrazol-5-amine (J-lll) (1 eq., 40 g) was dissolved in dilute HCI (120 ml of HCI in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0 – 5 C over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2C03. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 C. After complete reaction, the reaction mixture was extracted with EE (3 x 500 ml), the combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum. The purification (Si02, 20 % EE/hexane) of the residue by column chromatography produced a white solid (J- IV) (6.5 g, 15.1 % yield).

The synthetic route of 3-Amino-5-tert-butylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2012/62462; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics