Tag: M.W:100-200

Synthetic Route of 1152582-56-3, 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 1152582-56-3 as follows.

Example 22 N-(5-(4-fluorophenyl)-11-methyl-1-oxo-2,4,5,11-tetrahydro-1H-2,5,6,11-tetraazadibenzo[cd,h]azulen-8-yl)-2-(1-methyl-1H-pyrazol-4-yl)acetamide [0706] A stock solution of Example 14e and N,N-diisopropylethylamine (0.11 M and 0.33 M in N,N-dimethylacetamide, respectively, 350 muL, 0.038 mmol Example 14e and 0.11 mmol N,N-diisopropylethylamine), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.13 M in N,N-dimethylacetamide, 350 muL, 0.046 mmol), and 2-(1-methyl-1H-pyrazol-4-yl)acetic acid (0.40 M in N,N-dimethylacetamide, 113 muL, 0.050 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100 C., and passed through the reactor at 180 muL per minute (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified by reverse phase HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) to yield the title compound as an impure mixture. The material was dissolved in methanol (1 mL) and manually injected into the HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) give 0.0067 g (38%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) delta 8.49 (d, J=2.44 Hz, 1H), 8.45 (d, J=2.75 Hz, 1H), 7.77 (s, 1H), 7.63 (s, 1H), 7.40 (s, 1H), 7.07 (s, 1H), 6.87 (m, 2H), 6.57 (m, 2H), 4.60 (m, 2H), 4.07 (s, 3H), 3.81 (s, 3H), 3.55 (s, 2H). MS (APCI+) m/z 484.1 (M+H)+.

According to the analysis of related databases, 1152582-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Dachun; Pratt, John; Wang, Le; Hasvold, Lisa A.; Bogdan, Andrew; US2014/256710; (2014); A1;,
Pyrazole – Wikipedia,
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Some common heterocyclic compound, 1128-54-7, name is 3-Methyl-1-phenyl-1H-pyrazole, molecular formula is C10H10N2, 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. Safety of 3-Methyl-1-phenyl-1H-pyrazole

General procedure: To a stirred solution of 1-phenyl-1H-pyrazole (5a) (288 mg, 2.00 mmol, 1.00 equiv.) in dryTHF (2.00 mL/mmol based on 5a), 1.64 M solution of n-BuLi in n-hexane (1.34 mL, 2.20mmol, 1.10 equiv.) was added dropwise at -78 C under an argon atmosphere. After being stirred at the same temperature for 1 h, benzoyl chloride (6a) (0.260 mL, 2.20 mmol, 1.10equiv.) was added to the mixture. After being warmed to room temperature and stirred at the same temperature for 18 h, the reaction mixture was quenched with saturated NH4Cl aq. The aqueous layer was extracted with ethyl acetate. The combined extract was washed with brine,dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel with hexane : EtOAc = 5 : 1 to give phenyl(1-phenyl-1H-pyrazol-5-yl)methanone (7a) as a white solid (429 mg, 1.73 mmol, 86%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1128-54-7, its application will become more common.

Reference:
Article; Fuse, Shinichiro; Kadonosono, Tetsuya; Kizaka-Kondoh, Shinae; Kuchimaru, Takahiro; Nakamura, Hiroyuki; Sato, Shinichi; Suzuki, Kensuke; Ueda, Hiroki; Bioorganic and medicinal chemistry; (2019);,
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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 105434-90-0 as follows. Application In Synthesis of Ethyl 5-amino-1H-pyrazole-3-carboxylate

[00383] To a solution of ethyl 5-amino-1H-pyrazole-3-carboxylate (1.55 g, 10 mmol) in AcOH (20 mL) was added 4,4,4-trifluoro-1-(4-methoxyphenyl)butane-1,3-dione (2.71 g, 11 mmol). The mixture was refluxed for 5 h and subsequently cooled down to 0 C in an ice bath. The precipitate was collected by filtration and recrystallized by hexanes/ethyl acetate to give a yellow solid. The solid was taken in MeOH (20 mL) and NaOH aq. (1M, 20 mL), and the solution was stirred at room temperature for 5 h. The solvent was then removed and the residue was acidified by 1M HC1 until PH 2. The precipitate was collected by filtration, and washed with cold water. The resulting solid was dried to obtain the pure product as a pale yellow solid (1.55 g, 92% yield). ?H NMR (400 MHz, DMSO-d6) oe 13.57 (s, 1H), 8.26-8.22 (m, 3H), 7.39 (d, J = 7.9 Hz, 2H), 7.32 (s, 1H), 2.39 (s, 3H).

According to the analysis of related databases, 105434-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; YUAN, Yiyuan; ZHANG, Yongyou; READY, Joseph; HU, Bin; (228 pag.)WO2018/145080; (2018); A1;,
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Application of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Following the procedure described in Example 1 wherein 2-methoxyethanol was used as the solvent instead of ethanol, 76percent of the product was obtained with m. p. 184-187 °C.

The synthetic route of 3-Amino-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENTIVA, A.S.; WO2004/37824; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 360056-45-7,Some common heterocyclic compound, 360056-45-7, name is Methyl 4-amino-1H-pyrazole-3-carboxylate, molecular formula is C5H7N3O2, 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.

methyl 4-amino-1H-pyrazole-3-carboxylate (1.0 g, 7.09 mmol) and triethylamine (1.5 mL, 8.5 mmol) were stirred in dioxane (10 mL) at 0C. A solution of 2,6- dichlorobenzoyl chloride (1.5 g, 7.17 mmol) in THF (5 mL) was added dropwise until the starting material was consumed. The reaction was filtered, and the resultant solid washed with dioxane (3 x 20 mL). The filtrates were combined and used directly in the next reaction. MS (ESI) m/z 315 (M + H)+. Expected mass from chemical formula C12H9N3O3: 314.12 Da

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; FERGUSON, Fleur, M.; DOCTOR, Zainab, M.; (0 pag.)WO2020/5807; (2020); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, 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 25700-12-3, HPLC of Formula: C8H7N3

To a solution of 3-(1H-pyrazol-1-yl)pyridine (5 g, 34.4 mmol) in acetonitrile (68.9 ml) was added N-bromosuccinimide (7.97 g, 44.8 mmol). The reaction mixture was stirred at ambient temperature for 3H. The reaction mixture was diluted with EtOAc and washed with H2O, the organics were dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 0-60% EtOAc in hexanes to afford 3-(4-bromo-1H-pyrazol-1-yl)pyridine as a tan solid (6.99 g, 91%): mp 126-127 C.; 1H NMR (400 MHz, acetone-d6) delta 9.12 (d, J=2.5 Hz, 1H), 8.64 (d, J=0.5 Hz, 1H), 8.58 (dd, J=4.7, 1.4 Hz, 1H), 8.23 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.85 (s, 1H), 7.56 (ddd, J=8.3, 4.7, 0.7 Hz, 1H); EIMS m/z 223.

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-(1H-Pyrazol-1-yl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
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Reference of 18213-75-7,Some common heterocyclic compound, 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, molecular formula is C5H8N4O, 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 5-amino-1-methyl-1H-pyrazole-4-carboxamide (0.200 g, 1.4 mmol) in ethanol (10 mL) were added ethyl 2,2,2-trifluoroacetate (0.123 g, 8.6 mmol) and sodium hydride (60% suspension in mineral oil, 0.571 g, 14.8 mmol) with stirring at 25 C. The reaction solution was degassed with nitrogen for 3 times and stirred at 90 C for 16 h. The resulting mixture was cooled toroom temperature and concentrated under reduced pressure. The residue was partitioned between aqueous hydrochloride acid (iN, 10 mL) and ethyl acetate (20 mL). The separated aqueous layer was extracted with ethyl acetate (2 x 15 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous sodium sulfate. The solids were filtered out and the filtrate was concentrated under vacuum. The title compound was obtained as a solid and used in next stepdirectly without further purification. MS (+ESI) m/z = 219.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FORSTER, Ashley; CHEN, Yili; DWYER, Michael, P.; BERGER, Richard; WANG, Ming; NANDA, Kausik K.; BUNDA, Jaime L.; SHIPE, William D.; (100 pag.)WO2016/209749; (2016); A1;,
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Reference of 82560-12-1, 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step j04: 3-Tert-butyl-1H-pyrazol-5-amine (J-III) (1 eq., 40 g) was dissolved in dilute HCl (120 ml of HCl 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 Na2CO3. 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 (3×500 ml), the combined organic phases were dried over sodium sulfate and the solvent was removed under vacuum. The purification (SiO2, 20% EE/hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15.1% yield).

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-5-tert-butylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; US2012/115893; (2012); 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. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 181585-93-3

To a solution of 2-methyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester and 1-methyl-5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.18 g, 6.37 mmo 1) in tetrahydro furan (20 mL) at 0C was added a lithium aluminum hydride solution (1 .OM in tetrahydrofuran, 7.65 mL, 7.65 mmol) drop wise. The resulting mixture was stirred at 0C for 20 min. To this solution was added ethyl acetate (1 mL) followed by few crystals of sodium sulphate decahydrate. The resulting mixture was stirred for 30 min then filtered, the filter cake washed with ethyl acetate and the filtrate evaporated. The residue was purified by flash chromatography (silica gel, 80 g, 50% to 70% ethyl acetate in hexanes) to give 1-methyl-3-nitro-1H-pyrazol-5-yl)methanol (496 mg, 50%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (s, 3 H) 4.53 (d, J=5.67 Hz, 2 H) 5.55 (t, J=5.48 Hz, 1 H) 6.93 (s, 1 H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BROTHERTON-PLEISS, Christine; JAIME-FIGUEROA, Saul; LOPEZ-TAPIA, Francisco Javier; LOU, Yan; OWENS, Timothy D.; WO2013/24078; (2013); A1;,
Pyrazole – Wikipedia,
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Related Products of 1613191-73-3, The chemical industry reduces the impact on the environment during synthesis 1613191-73-3, name is Allyl 3,5-diamino-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Step 2: 3-allyl 7-tert-butyl 2-amino-5, 6-dihydropyrazolo[l,5-a]pyrido[4,3-d]pyrimidine- 3, 7(8H)-dicarboxylate 4. [00239] A mixture of tert-butyl 3-(l,3-dioxolan-2-yl)-4-oxo-piperidine-l-carboxylate (100 mg, 0.3686 mmol), allyl 3,5-diamino-lH-pyrazole-4-carboxylate (67.15 mg, 0.369 mmol), KOH (5 mg, 0.0891 mmol) in dioxane (2 mL) was stirred at ambient temperature for 18h. The solid that formed was filtered and triturated in Et20 to afford compound 4 as a beige solid (lOOmg, 73%). LC-MS (M+H)+ 334.2; NMR (500 MHz, DMSO-d6) delta 8.85 (s, 1H), 6.37 (s, 2H), 6.00-6.07 (m, 1H), 5.51-5.55 (d, 1H), 5.23-5.26 (m, 1H), 4.75-4.76 (m, 2H), 4.55 (s, 2H), 3.69 (m, 2H), 3.32 (s, 2H), 2.93-2.95 (m, 2H), 1.40 (s, 9H).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; WO2014/143240; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics