Tag: M.W:100-200

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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, A new synthetic method of this compound is introduced below., Product Details of 3524-32-1

General procedure: In a 50 mL single-mouth flask,Salicylaldehyde (1 mmol) was added in sequence,Ethyl cyanoacetate (1 mmol) and 3-methyl-1-phenyl-5-aminopyrazole (1 mmol),Triethylamine (0.1 mmol) and ethanol (8 mL),The reaction was stirred under reflux for 8 h.After the reaction is over,Cool to room temperature.Rotate the solvent under reduced pressure,Get a rough product,The crude product was recrystallized from 95% ethanol.5-amino-1-methyl-3-phenylcoumarin[4,3-d]pyrazolo[3,4-b]pyridine-6(3H)-one (Ia):Yield 63%

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; Soochow University (Suzhou); Shi Daqing; Zhang Mengye; Xu Wentao; Wang Ning; Huang Zhibin; (17 pag.)CN108409748; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 51105-90-9,Some common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, molecular formula is C5H6N2O2, 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.

DIAD (9.39 ml, 43.61 mmol) was added dropwise to an ice-cooled solution of methyl 1 H-pyrazole-4- carboxylate (5 g, 39.65 mmol), tert-butyl (2-hydroxyethyl)carbamate (6.13 ml, 39.65 mmol) and PPrtj (1 1 .44 g, 43.61 mmol) in THF (300 ml). The reaction was then allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was quenchedwith water (150 ml) and the layers separated. The aqueous layer was extracted using EtOAc (3 x 150 ml). The combined organic layers were washed with brine, dried (MgS04), filtered and the solvent evaporated to give the crude product. Purification by flasn column chromatography (eluting with a gradient of 15-100% EtOAc / heptane) gave the title compound (1 1 .3 g, 68%) as a white solid. 1 H-NMR (CDCI3, 500 MHz): d[ppm]= 7.93 (s, 1 H), 7.87 (s, 1 H), 4.25 (t, J = 5.3 Hz, 2H), 3.83 (s, 3H), 3.61- 3.54 (m, 2H), 1.44 (s, 9H) HPLCMS (Method A): [m/z]: 270.1 [M+Hf

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
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 56984-32-8 as follows. name: Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate

Example 12; [Show Image] Compound 6 was reacted with various benzylbromides in the presence of cesium carbonate to give Compounds A-26, A-27 and A-28.

According to the analysis of related databases, 56984-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; EP1953145; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 121507-34-4, name is 5-Isopropoxy-1H-pyrazol-3-amine, 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 121507-34-4, Safety of 5-Isopropoxy-1H-pyrazol-3-amine

Method 2; 2,5-Dichloro-N-(5-isopropoxy-lH-pyrazol-3-yl)pyrimidin-4-amine; A solution of 2,4,5-trichloropyrimidine (533 mg, 2.93 mmol), 5-isopropoxy-lH- pyrazol-3 -amine (413 mg, 2.93 mmol) and triethylamine (0.49 ml) in TetaF (5 ml) was stirred at room temperature for 10 hours. Solvent was removed and EtOAc was added. The solution was washed with water and dried over anhydrous sodium sulfate and was concentrated to give title compound as a white solid (582 mg, 69%). LC-MS, 246 (M-42); 1H nuMR (CDCl3) delta 8.19 (s, IH), 7.80 (s, IH)5 5.79 (s, IH), 4.65 (m, IH), 1.30 (d, 6H).

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; WO2007/49041; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

Degassed toluene (sparged with argon for 25 mins, 10.0 mL) was added to a mixture of 3-bromo-5-fluorobenzylalcohol (1.00 g, 4.88 mmol), 3-tert-butyl-lH-pyrazole- 5-amine (678 mg, 4.88 mmol), copper (I) iodide (46.0 mg, 0.24 mmol) and potassium carbonate (1.41 g, 10.2 mmol). Trans-N,N’-dimethylcyclohexanediamine (154 mu^, 0.98 mmol) was added and the reaction heated to 150 C for 18 h using microwave irradiation. The mixture was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried (MgS04), filtered and evaporated in vacuo. The residue was purified by FCC, using 0- 100% EtOAc in cyclohexane, to give the title compound (307 mg, 24%). LCMS (Method 4): Rt 2.34 min, m/z 264 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-5-tert-butylpyrazole, its application will become more common.

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

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. 180207-57-2, name is 2-(1H-Pyrazol-4-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(1H-Pyrazol-4-yl)ethanol

EXAMPLE 242 l-(5-(4-(2 -hydroxy ethyl)-lH-pyrazol-l-yl)-4-(isopropylamino)pyridin- -b]pyridine-5-carbonitrile In a 20 mL microwave vial, l-(5-iodo-4-(isopropylamino)pyridin-2-yl)-lH- pyrazolo[3,4-b]pyridine-5-carbonitrile (50 mg, 0.12 mmol), 2-(lH-pyrazol-4-yl)ethanol (13.9 mg, 0.12 mmol), potassium carbonate (51.3 mg, 0.37 mmol) and Nl,N2- dimethylethane-l,2-diamine (6.54 mg, 0.074 mmol) were mixed in 1,4-dioxane (1 mL) at room temperature with stirring. While bubbling in nitrogen, copper(I) iodide (4.71 mg, 0.025 mmol) was added and the mixture was capped and heated with stirring at 110 C for 5 hours. After cooling, the reaction mixture was filtered, and the filtrate was concentrated under high vacuum and the residue was dissolved in DMF for purification. The product was purified via preparative HPLC to afford l-(5-(4-(2-hydroxyethyl)-lH- pyrazol-l-yl)-4-(isopropylandno)pyridin-2-yl)-lH-pyrazolo[3,4-b]pyridine-5-carbonitrile (4.4 mg, 8% yield). NMR (500MHz, DMSO-de) delta 9.11-8.97 (m, 2H), 8.65 (br s, IH), 8.36 (br s, IH), 8.17 (s, IH), 7.77 (s, IH), 7.39 (br s, IH), 7.26 (d, J=7.3 Hz, IH), 4.76 (br s, IH), 3.84-3.74 (m, IH), 3.67-3.59 (m, 2H), 2.67 (t, J=6.9 Hz, 2H), 1.24 (d, J=6.2 Hz, 6H); LC/MS: 389.0 (M+H); HPLC rt 1.37 min, conditions C.

According to the analysis of related databases, 180207-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
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 26308-42-9 as follows. category: pyrazoles-derivatives

Example 252 Production of N-{2-chloro-5-[(2-{[(2-methylcyclopropyl)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide Using 3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid (181 mg, 1.17 mmol), tetrahydrofuran (4.5 mL), N,N-dimethylformamide (30 muL, 0.39 mmol), oxalyl chloride (102 muL, 1.17 mmol), N-[6-(3-amino-4-chlorophenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-methylcyclopropanecarboxamide (300 mg, 0.84 mmol) and N,N-dimethylacetamide (6.0 mL), and in the same manner as in Example 249, the title compound (207 mg, 50%) was obtained as a white powder. 1H-NMR (DMSO-d6, 300 MHz) delta 0.61-0.73 (1H, m), 0.97-1.04 (1H, m), 1.05-1.09 (3H, m), 1.16-1.25 (1H, m), 1.19 (3H, t, J=7.5 Hz), 1.62-1.73 (1H, m), 2.55 (2H, q, J=7.5 Hz), 3.99 (3H, s), 6.88 (1H, s), 7.08 (1H, d, J=9.5 Hz), 7.21-7.27 (1H, m), 7.53 (1H, d, J=3.0 Hz), 7.62 (1H, d, J=8.7 Hz), 7.94 (1H, s), 8.05 (1H, d, J=9.5 Hz), 10.00 (1H, s), 10.99 (1H, s).

According to the analysis of related databases, 26308-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (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. 2075-46-9, name is 4-Nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Formula: C3H3N3O2

General procedure: To a stirred solution of 4-nitroimidazole or 4-nitropyrazole (1.00 g, 8.84 mmol) in DMF (6.00 mL) at 25C were added K2CO3 (1.47 g, 10.6 mmol) and alkyl iodide(10.6 mmol). After stirring for 16 h at 25 C, the reactionmixture was treated with water (15 mL) and EtOAc (20 mL)and transferred to a 125 mL separatory funnel. The organiclayer was collected and the aqueous layer was extracted withEtOAc (25 mL × 2). The combined organic layers werewashed with brine (20 mL), dried over sodium sulfate andfiltered. The filtrate was concentrated, and the residue waspurified by flash column chromatography to provide thecorresponding alkyl azole.

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; Jung, Haeun; Bae, Seri; Jang, Ha-Lim; Joo, Jung Min; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3009 – 3014;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature 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.

INTERMEDIATE 8 4-(3 -Iodo- lH-p yrazol- 1 – vPbenzonitrile To 3-iodo-lH-pyrazole (801 mg, 4.13 mmol) in DMSO (10 mL) at 0 C, was added sodium hydride (60% in mineral oil, 198 mg, 4.95 mmol). The reaction was warmed to 25 C and stirred for 60 min before methyl 4-fluorobenzonitrile (500 mg, 4.13 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combifiash, 0-30% EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l-yl)benzonitrile, as a pale yellow crystaline solid. LCMS calc. = 295.96; found = 295.90 (M+H)+. NMR (500 MHz, CDC13): delta 7.83 (m, 3 H); 7.78 (d, J= 8.5 Hz, 2 H), 6.71 (d, J= 2.6 Hz, 1 H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); 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. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Methyl-1H-pyrazole-5-carbaldehyde

Acetic acid (0.4 mL) was added to a solution of 2-methyl-2H-pyrazole-3-carbaldehyde (0.8 g) and 5-bromopyridine-2,3-diamine (1 g) in THF (20 mL) at room temperature. The mixture was stirred overnight at room temperature. The mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, dried over magnesium sulfate, and then concentrated to obtain a residue. Sodium borohydride (300 mg) was added to a solution of the residue in THF (20 mL)/methanol (50 mL) at 0C, and the mixture was stirred for 1 hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was sequentially washed with water and a saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to obtain a pale yellow solid as 5-bromo-N3-((1-methyl-1H-pyrazol-5-yl)methyl)pyridine-2,3-diamine (0.38 g). A mixture of the obtained pale yellow solid (300 mg), acetic acid (0.1 mL), DMAP (10 mg), propylphosphonic anhydride (50% in ethyl acetate solution) (0.938 mL), DIPEA (0.464 mL) and THF (10 mL) was stirred under microwave irradiation at 200C for 2 hours. The mixture was purified by NH silica gel column chromatography (methanol/ethyl acetate) to obtain the title compound (188 mg). 1H NMR (300 MHz, DMSO-d6) delta 2.55 (3H, s), 3.81 (3H, s), 5.63 (2H, s), 5.70 (1H, d, J = 1.9 Hz), 7.30 (1H, d, J = 1.9 Hz), 8.24 (1H, d, J = 2.2 Hz), 8.42 (1H, d, J = 2.2 Hz).

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KAWAKITA Youichi; KOJIMA Takuto; NII Noriyuki; ITO Yoshiteru; SAKAUCHI Nobuki; BANNO Hiroshi; LIU Xin; ONO Koji; IMAMURA Keisuke; IMAMURA Shinichi; (165 pag.)EP3450436; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics