Day: July 12, 2021

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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H7N3

[00205] Step 1 : 5-Amino-l -methyl- lH-pyrazole (6.25 g, 64.4 mmol) was dissolved in THF (120 ml) and treated with sodium hydride (3.51 g, 87.8 mmol). The reaction was heated to 35 C for 30 minutes and then treated with a dimethylformamide (“DMF”) solution (24 mL) of 4-bromo-2-fluoropyridine (10.3 g, 58.5 mmol). The reaction was heated to 50 C and stirred for 1 hour. The reaction was allowed to cool and treated with water, and the organics were concentrated. The residue was diluted with ethyl acetate and washed with water and brine. The organics were dried over Na2S04, filtered and concentrated. The material was purified on silica gel eluting with 30-100% ethyl acetate/hexanes followed by 25% methanoLDCM to afford 4-bromo-N-(l-methyl-lH-pyrazol-5-yl)pyridin-2-amine (6.55 g, 25.9 mmol, 44.2% yield).

The synthetic route of 1192-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; COOK, Adam; GAUDINO, John; GUNAWARDANA, Indrani, W.; HICKEN, Erik, James; HUNT, Kevin, W.; LYON, Michael; METCALF, Andrew, T.; MOHR, Peter, J.; MORENO, David, A.; NEWHOUSE, Brad; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; GAZZARD, Lewis; SCHMIDT, Jane; DO, Steve; WO2015/103137; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 67-51-6, 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. 67-51-6, name is 3,5-Dimethyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3,5-Dimethyl-1H-pyrazole, 78.5 g (0.818 mol), was dissolved in 700 mL of water heated to 70°C, and 517 g (3.271 mol) of potassium permanganate was added to the hot solution, maintaining the temperature no higher than 90°C. The mixture was cooled to room temperature, the precipitate of MnO2 was filtered off and washed with water, and the filtrate was acidified with aqueous HCl to pH 2 and left overnight. The precipitate was filtered off and washed with water. Yield 41.75 g (33percent), white crystals, mp 257?258°C. 1H NMR spectrum: delta 7.07 ppm, s (1H, 4-H). 5-Methyl-1H-pyrazole-3-carboxylic acid (2). The aqueous filtrate obtained after separation of diacid 1, was neutralized to pH 5?6, and the precipitate of 2 was filtered off and washed with water. Yield 18.1 g (18percent), white crystals, mp 210?211°C. 1H NMR spectrum, delta, ppm: 2.25 s (3H, CH3), 6.42 s (1H, 4-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, 3,5-Dimethyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kharaneko; Russian Journal of Organic Chemistry; vol. 52; 9; (2016); p. 1322 – 1325; Zh. Org. Khim.; vol. 52; 9; (2016); p. 1334 – 1337,4;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 132712-71-1, A common heterocyclic compound, 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol, molecular formula is C4H6N2O, 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: To a neat solution containing 11H-indeno[1,2-b]quinoxalin-11-one (1 mmol), pyrazolone (1 mmol), and malononitrile (1 mmol), 10% mol of Na2CO3 in ethanol(10 mL) was added. The reaction mixture was heated at 70 8C for 12 h. After completion of the reaction as indicated by TLC, the precipitate was filtrated and washed with cold ethanol to afford the pure product 8. 4.5 6′-Amino-3′-methyl-1’H-spiro [indeno[1,2-b] quinoxaline-11, 4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile (8a) Light green powder (0.36 g, yield 93%). Mp 263-266 C. IR (KBr) (vmax/cm-1): 3450, 3274, 3250, 3112, 2976, 2191, 1637, 1607, 1465, 1401. 1H NMR (250 MHz, DMSO-d6): deltaH (ppm) 1.12 (3H, s, CH3), 7.45-8.13 (10H, m, H-Ar and NH2), 12.51 (1H, s, NH). C NMR (62 MHz, DMSO-d6): deltaC (ppm), 9.5 (CH3), 56.5 (C-Spiro), 96.8 (C-CN), 119.3 (CN), 121.4, 122.1, 126.2, 129.4, 129.6, 130.1, 130.8, 133.5, 135.5, 136.0, 141.8,142.5, 151.4, 153.3, 155.9, 162.9 (C-Ar and C-Pyrazole), 164.8 (C-NH2). Anal. calcd for C22H14N6O: C, 69.83; H, 3.73; N, 22.21. Found: C, 69.88; H, 3.72; N, 22.22.

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:
Article; Soleimani, Ebrahim; Hariri, Mina; Saei, Parisa; Comptes Rendus Chimie; vol. 16; 9; (2013); p. 773 – 777;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, molecular formula is C5H8N2O, 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 1,3-Dimethyl-1H-pyrazol-5-ol

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)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5203-77-0, its application will become more common.

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;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35691-93-1, name is Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate, 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 35691-93-1, HPLC of Formula: C8H12N2O2

3,5-Dimethyl-1H-pyrazole-carboxylic acid ethyl ester(0.83 g, 5 mM), potassium carbonate (2.07 g, 15 mM), tetrabutylammonium bromide(0.11 g, 0.25 mM), and ethyl bromoacetate (3.32 mL, 5 mM) were mixed in 1,4-dioxane(60 mL). The reaction mixture was stirred at 140 C for 24 h and the solvent was removedby evaporation. The residue was dissolved in CH2Cl2 (40 mL) and washed with deionized water (200 mL). The organic layer was dried over MgSO4 and evaporated to give 1-ethoxycarbonylmethyl-3,5dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester (Ecmdpcaee) as afaint yellow oil. Yield: 0.78 g (78.7%). 1H NMR (CDCl3, 500 MHz) delta: 4.80 (s, 2H), 4.16(q, 2H), 4.24 (q, 2H), 2.47 (s, 3H), 2.42 (s, 3H), 1.36 (t, 3H), 1.28 (t, 3H); ESI-MS: m/z(%) 254.95 [MH+] (100%), 274.10[MK+] (100%); IR (cm-1, KBr pellet): 3378 (m), 2985 (vs), 2931 (vs), 2587 (w), 1735 (vs), 1702 (s), 1656 (w), 1552 (s), 1447 (m), 1374 (s), 1356 (w), 1282 (s), 1233 (vs), 1160 (w), 1051 (w), 873 (m), 686 (m); m.p.: 50-52 C.

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, Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xia, Qinghong; Ren, Yanqiu; Cheng, Mei-Ling; Liu, Xiuxiu; Chen, Sheng; Zhai, Changwei; Liu, Qi; Journal of Coordination Chemistry; vol. 68; 10; (2015); p. 1688 – 1704;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 179692-08-1, These common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-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.

A suspension of Intermediate 74b (2.72 g, 10.2 mmol) in acetonitrile (27 mL) was treated with caesium carbonate (5.0 g, 15.3 mmol) then 2-(2- bromoethoxy)tetrahydro-2H-pyran (1.70 mL, 11.2 mmol) and the mixture was stirred at 60 C for 3.5 h. The mixture was evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (2 x). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried (Na2S04), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, isolating the lower running spot to give the title compound as a colourless glass (1.57 g, 39%). LCMS (Method 3): Rt 3.67 min, m/z 417 [M+Na+].

The synthetic route of 179692-08-1 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

Electric Literature of 1227611-94-0,Some common heterocyclic compound, 1227611-94-0, name is 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, molecular formula is C9H11IN2O, 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.

Intermediate 25: 2-[4-(4-lodo-pyrazol-1 -yI)-cyclohexylamino]-ethanol 2-Amino-ethanol (0.30 mL; 4.96 mmol; 1.4 eq.) was added in one portion to a solution of4-(4-Iodo-pyrazol-1-yl)-cyclohexanone (intermediate 20; 1.00 g; 3.45 mmol; 1.0 eq.) inEtOH. After 1 h the reaction solution was cooled to 0C and NaBH4 (290 mg; 7.67 mmol;2.2 eq.) added portionwise over 1 mm. After a further 1 h the reaction suspension waspoured into 1 N NaOH solution and extracted with DCM. Combined organic phases werewashed with brine, dried over magnesium sulfate, filtered and concentrated. Purificationusing a SCX-2 cartridge afforded the title compound as a white solid (1.00 g; 84%). 1 HNMR (300 MHz, DMSO) oe 7.94 (s, 1H), 7.49 (s, IH), 4.47 (brs, 1H), 4.12 (m, 1H), 3.45(m, 2H), 2.60 (t, J = 5.8 Hz, 2H), 2.41 (m, 1H), 2.95 (m, 4H), 1.72 (m, 2H), 1.13 (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 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, its application will become more common.

Reference:
Patent; ARES TRADING S.A.; CROSIGNANI, Stefano; JORAND-LEBRUN, Catherine; GERBER, Patrick; MUZERELLE, Mathilde; WO2014/8992; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, molecular formula is C5H7N3O3, 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 C5H7N3O3

General procedure: To 17a (1 g, 7.8 mmol) in EtOH (20 mL) was added 10% Pd/C50 mg. The reaction mixture was stirred for 3 h under hydrogen at roomtemperature. The mixture was then filtered with Celite, and the filtratewas concentrated and dried under vacuum to yield 0.74 g (97%) of 18aas a white solid. MS (ESI) m/z 98 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42027-81-6, its application will become more common.

Reference:
Article; Yu, Ru-Nan; Chen, Cheng-Juan; Shu, Lei; Yin, Yuan; Wang, Zhi-Jian; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1646 – 1657;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 139308-52-4, These common heterocyclic compound, 139308-52-4, name is Ethyl 3-bromo-1-methyl-1H-pyrazole-4-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.

[1302] to a solution of ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate (500 mg, 2.15 mmol) and NCS (574 mg, 4.30 mmol) was stirred. The mixture was stirred at 160 C for 3h under N2. The reaction mixture was added by addition of cc (20 ml), and then diluted with NaHCO3 (30 ml). The mixture was extracted with DCM (20 ml x 3). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by preparatory- tlc (SiO2, pe:ea = 5: 1). Compound 274a (180 mg, yield: 31.30%) was obtained as a yellow oil. 1H NMR (400mhz, CDCl3) delta 4.34 (q, = 7.1 hz, 2h), 3.85 (s, 3h), 1.46 – 1.24 (m, 3h). MS (ESI) m/z (M+H)+266.9.

The synthetic route of 139308-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., name: 1H-Pyrazole-4-carbaldehyde

4-FORMYL-PYRAZOLE-1-CARBOXYLIC acid tert-butyl ester (56). To a solution of 55 (0.31 g, 3.26 mmol) in acetonitrile (30 ml) was added BOC anhydride (0.71 g, 3.26 mmol) followed by DMAP (0.02 g). After 30 minutes of stirring at room temperature, the solvent was evaporated, water and EtOAc were added. Organic layer was separated, washed with 0.5 N HCl (10 ml) and brine (15 ml), dried (NA2S04) and concentrated to give 0.41 g (76percent yield) of the desired product which was used in the next step to prepare di-Boc-protected 2 without purification.

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; IMCLONE SYSTEMS INCORPORATED; WO2005/813; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics