Tag: M.W:100-200

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. 90253-21-7, name is 4-Cyclopropyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Cyclopropyl-1H-pyrazole

Preparation 23b: {3-[4-(4-cyclopropylpyrazol-1 -yl)benzyl]-4-difluoromethoxy-2-ethyl- 8-fluoroquinolin-5-yloxy}acetic acid methyl ester; A mixture of (4-{[4-difluoromethoxy-2-ethyl-8-fluoro-5-(2-methoxy-2-oxoethoxy) quinolin-3-yl]methyl}phenyl)boronic acid (0.1 g), 4-cyclopropyl-1 H-pyrazole (0.047 g), cuprous acetate (0.078 g) and pyridine (3 ml_) was heated at 40 0C for 24 hours. The mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and then concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1 :0 to 7:3 by volume) gave title compound as pale green oil (0.09 g).MS: ESI (+ve) (Method B): 526 (M+H)+, Retention time 4.5 min

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 90253-21-7.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2008/122784; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 3273-44-7, 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. 3273-44-7, name is 5-Methyl-1H-pyrazole-3-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: tert-Butyl 3-formyl-5-methyl-lH-pyrazole-l-carboxylate 5-Methyl-lH-pyrazole-3-carbaldehyde (5.4 g, 49 mmol) was dissolved in acetonitrile (200 mL) and cooled to 0 C with stirring. DMAP (0.60 g, 4.9 mmol) and di-tert-butyldicarbonate (12.9 g, 59.q mmol) were added and the solution was allowed to warm to rt and stir for 16 h. The reaction was diluted with EtOAc (200 mL). Then the mixture was washed with IN HC1 (aq.) (2xl00mL), saturated aq NaHC03 (2xl00mL), dried over magnesium sulfate, filtered and concentrated. The residue was purified on silica gel to give tert-butyl 3-formyl-5-methyl-lH-pyrazole-l-carboxylate (3.9 g, 38%) as a clear oil. ‘H NMR (CDC13) delta 10.10 (s, 1H), 6.65 (s, 1H), 2.60 (s, 3H), 1.72 (s, 9H).

The synthetic route of 5-Methyl-1H-pyrazole-3-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
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. 796729-10-7, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid

Step 3: Synthesis of tert-butyl(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)carbamate (CF72) CF70 (280 mg, 1.84 mmol) was mixed with tert-butanol (6 mL) and triethyl amine (0.8 mL, 4 mmol). Diphenyl phosphoryl azide (0.71 mL, 3.31 mmol) was added via a syringe and the mixture was stirred at ambient temperature for overnight. The solution was heated at reflux for 24 h. The volatile components were removed on a rotary evaporator and the residue was purified by flash column chromatography. CF72 was isolated in 224 mg. 1H NMR (300 MHz, CDCl3): 7.36 (s, 1H), 6.24 (s, 1H), 4.05 (t, J=7.31 Hz, 2H), 2.98-2.82 (m, 2H), 2.60-2.44 (m, 4H), 1.46 (s, 9H). 13C NMR (75 MHz, CDCl3): 153.76, 137.82, 137.01, 114.08, 80.10, 48.23, 28.48, 26.26, 23.63. ESI-MS calculated for C11H18N3O2 [M+H]+=224.14, Observed: 224.58.

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 796729-10-7.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1204298-65-6, name is 5-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, 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. Computed Properties of C6H6F2N2O2

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.41 mmol), 5-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (0.080 g, 0.45 mmol), pyridine (0.15 mL, 1.83 mmol) in acetonitrile (4 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.61 mL, 1.02 mmol). The sealed tube was heated to 100 C. for 16 h. After cooling, the precipitate was collected by filtration and washed with cold 1:1 acetonitrile/water to give 5-(difluoromethyl)-1-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-1H-pyrazole-4-carboxamide (0.119 g, 72%). 1H NMR (400 MHz, DMSO-d): delta 12.74 (bs, 1H), 10.19 (s, 1H), 8.45 (s, 1H), 7.74 (m, 1H), 7.69 (dd, 1H, J=8.4, 2.0 Hz), 7.56 (t, JHF=54 Hz, 1H), 7.53 (s, 1H), 6.90 (d, 1H, J=8.0 Hz), delta, 4.04 (s, 3H), 2.93 (t, 2H, J=7.2 Hz), 2.48 (partial masked under d-DMSO, m, 2H); MS (ESI): Calcd. for C18H15F2N5O2S: 403, found 404 (M+1)+.

The synthetic route of 1204298-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (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. 90253-21-7, name is 4-Cyclopropyl-1H-pyrazole, A new synthetic method of this compound is introduced below., name: 4-Cyclopropyl-1H-pyrazole

A mixture of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Example 18, step 1, 163 mg, 0.54 mmol), 4-cyclopropyl-1H-pyrazole (116 mg, 1.1 mmol), K2CO3(s) (149 mg, 1.1 mmol), copper (I) iodide (21 mg, 0.11 mmol), and (1R,2R)-N1,N2-dimethylcyclohexane-1,2- diamine (43 muL, 0.27 mmol) in DMF (5.38 mL) was sparged with Ar(g) and stirred at 110C until completion as determined by chromatographic (TLC or LC) monitoring. The resulting mixture was purified with silica chromatography (0 to 20% MeOH in DCM) to afford the title compound (115 mg, 75.5%). MS (apci) m/z = 284.1 [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; ARRAY BIOPHARMA INC.; BLAKE, James F.; DAI, Donghua; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI,, Gabrielle R.; METCALF, Andrew T.; MORENO, David A.; PRIGARO, Brett; REN, Li; (330 pag.)WO2019/143991; (2019); 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. 39846-84-9, name is Ethyl 5-nitro-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H7N3O4

(Step 3) Production of ethyl 5-amino-3-pyrazolecarboxylate To a solution of ethyl 5-nitro-3-pyrazolecarboxylate (331.48 g) in tetrahydrofuran (1.5 L) and ethyl acetate (1.5 L) was added 7.5% palladium carbon (30.036 g), and the mixture was stirred overnight at room temperature under a hydrogen atmosphere. The catalyst was filtered off, the filtrate was concentrated, and the resulting solid was recrystallized with ethyl acetate/hexane to obtain the title compound (265.38 g) as white crystals.

According to the analysis of related databases, 39846-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JAPAN TOBACCO, INC.; US2009/36450; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 948570-74-9,Some common heterocyclic compound, 948570-74-9, name is 1-(2-Methoxyethyl)-1H-pyrazol-4-amine, molecular formula is C6H11N3O, 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.

Example 2; N- [l-(2-methoxyethyl)pyrazol-4-yl] -2- [4-(6,7-dimethoxyqumolin-4-yloxy)phenyl] acetamide; 0 Diisopropylethylamine (0.124 ml) and 2-(7-azabenzotriazol-l-yl)-1,1,3,3-tetramethyluronium hexafiuorophosphate(V) (0.247 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimetlioxyquinolin-4-yloxy)phenyl]acetic acid (0.2 g), 4-amino- l-(2-methoxyethyl)pyrazole (0.092 g) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using a solvent gradient from 100:0 to 24:15 mixtures of methylene chloride and a 3.5M methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.106 g); 1H NMR: (DMSOd6) 3.21 (s, 3H), 3.62 (s, 2H), 3.63 (t, 2H), 3.92 (s, 3H), 3.94 (s, 3H), 4.12 (t, 2H), 6.47 (d, IH), 7.22 (d, 2H), 7.4 (s. IH), 7.44 (s, IH), 7.45 (d, 2H), 7.49 (s, IH), 7.89 (s, IH), 8.47 (d, IH), 10.2 (s, IH); Mass Spectrum: M+H+ 463.

The synthetic route of 948570-74-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99326; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1031351-95-7, The chemical industry reduces the impact on the environment during synthesis 1031351-95-7, name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

Preparation of hydroxylamine aqueous solution: Mix 3.13g hydroxylamine hydrochloride and 2.46g sodium acetate, Add 15mL water, The aqueous solution of hydroxylamine was prepared by stirring at room temperature. Dissolve 5.1 g (30 mmol) of 3-formyl-1-methyl-1H-pyrazole-5-carboxylic acid ethyl ester(I-1, R7=Me) (synthesized according to the reporting method of CN1278820) in 20 mL of THF, Add the prepared hydroxylamine aqueous solution dropwise at room temperature, and continue stirring for 2 hours after the drop . After complete reaction, THF was removed by desolvation, after adding water, filtering, washing with water and drying to obtain 4.95 g of white solid.

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, Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Chemical Institute Co., Ltd.; Sinochem Lantian Group Co., Ltd.; Peng Weili; Xing Jiahua; Li Jiao; Xu Tianming; Huang Hongying; Yu Jiping; (32 pag.)CN111362931; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 39846-84-9, 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. 39846-84-9, name is Ethyl 5-nitro-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester (0.925 g, 0.500 mmol) in absolute ethanol (10 cm3) was added 10% Pd/C (0.100 g). The mixture was stirred under an atmosphere of H2 at room temperature for 18 hours, filtered through Celite and the solvent removed under reduced pressure to give a green solid (0.70 g, 90%). 1H (CD3OD): 6.0 (s, IH), 4.3 (q, 2H, J=7.1, CO2CH2CH3), 1.4 (t, 3H, J=7.1,CO2CH2CH3). m/z (ES+): 156 [M+H]+

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-nitro-1H-pyrazole-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2006/127595; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001020-17-2, 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 1001020-17-2 as follows.

A mixture of A-i (750 mg, 4.93 mmol), A-2 (0.46 mL, 7.39 mmol) and K2C03 (2.72 g, 19.71 mmol) in 10 mL DMF is heated at 85 C for 3 hours. The reaction mixture is diluted with EtOAc, washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with 10-100% EtOAc in heptane to yield Intermediates A and B as a 10:1 mixture by 1HNMR.

According to the analysis of related databases, 1001020-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HUGHES, Robert Owen; LI, Xiang; NEMOTO, Peter Allen; SMITH KEENAN, Lana Louise; WU, Lifen; XIONG, Zhaoming; (65 pag.)WO2018/111803; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics