Tag: M.W:100-200

Electric Literature of 143426-49-7, A common heterocyclic compound, 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol, molecular formula is C10H10N2O, 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.

Example 4 N-[1-(6-{[4-(1H-pyrazol-1-yl)benzyl]oxy}-1-benzofuran-3-yl)ethyl]acetamide To a solution of N-[1-(6-hydroxy-1-benzofuran-3-yl)ethyl]acetamide (35.0 mg, 0.160 mmol) obtained in Reference Example 4 in THF (5 mL) were added [4-(1H-pyrazol-1-yl)phenyl]methanol (41.8 mg, 0.240 mmol), triphenylphosphine (63.0 mg, 0.240 mmol) and 2.2 M diethyl azodicarboxylate toluene solution (0.110 mL, 0.240 mmol), and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the obtained residue was purified by preparative HPLC to give the title compound (29.4 mg, yield 33%) as a white solid. preparation system: Waters large scale preparation system (UV Purification System)

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; Takeda Pharmaceutical Company Limited; EP2351743; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 28466-62-8,Some common heterocyclic compound, 28466-62-8, name is 1-Benzyl-1H-pyrazol-4-amine, molecular formula is C10H11N3, 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.

1 -(2-trimethylsilanyl-ethoxymethyl)-1 ,2-dihydro-pyridin-3-yl]-indole-1 -carboxylic acid tert-butyl ester, (1g, 1.46mmol), benzyl-1 H-pyrazole-4-yl amine (0.75g, 4.39mmol), 1- hydroxybenzotriazole hydrate (0.59 g, 4.39 mmol) and tetrahydrofuran (15ml_) were placed in a microwave vial. To this solution was added N,N-diisopropylethylamine (0.58g, 0.78mL, 4.49mmol) and N-p-dimethylaminopropyO-N’-ethylcarbodiimide hydrochloride (0.84g, 4.39mmol), the vial capped and heated in the microwave at 90 0C for 30 minutes. After cooling, the mixture was concentrated in vacuo and the residue partitioned between water and dichloromethane. The organic layer was separated and the aqueous was extracted with a further portion of dichloromethane. The combined dichloromethane layers were dried (Na2SO4) and concentrated in vacuo. The resultant crude product was purified by flash chromatography on SiO2 eluting with dichloromethane – 15% methanol / dichloromethane (gradient) to afford the desired title compound as a yellow foam, 1.Og, 82%.

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

Reference:
Patent; VERNALIS (R & D) LTD; WO2009/93012; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 873191-23-2, The chemical industry reduces the impact on the environment during synthesis 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

General procedure: The lycorine derivatives 10, 11 and 12 (0.1mmol) were dissolved in dry THF (10mL), and NaH (50mg, 2mmol) and 3-(bromomethyl)pyridine, 3-(Chloromethyl)-1,5-dimethyl-1H-pyrazole or 5-Bromomethyl-1,3-dimethyl-1H-pyrazole (1mmol) were added. The mixture was stirred at r. t. for 24h and quenched with H2O (50mL) in an ice bath. The solution was evaporated to remove the THF and extracted with CH2Cl2 (2×30mL). The organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using petroleum ether-EtOAc as the eluent to afford compounds 5, 6, 7, 8 and 9. 8-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-5-ethyl-4-methyl-5,6-dihydro- phenanthridine (5). 78% yield. Colorless amorphous powder (from CH2Cl2); 1H NMR (500MHz, CDCl3) delta 7.59 (d, J=8.5Hz, 1H), 7.50 (d, J=7.6Hz, 1H), 7.06 (d, J=8.0Hz, 1H), 7.00 (t, J=7.5Hz, 1H), 6.86 (dd, J=8.5, 2.6Hz, 1H), 6.74 (d, J=2.5Hz, 1H), 6.04 (s, 1H), 4.94 (s, 2H), 4.01 (s, 2H), 3.79 (s, 3H), 2.62 (q, J=7.1Hz, 2H), 2.29 (s, 3H), 2.19 (s, 3H), 1.01 (t, J=7.1Hz, 3H); 13C NMR (125MHz, CDCl3) delta 157.77 (C), 147.36 (C), 146.31 (C), 137.89 (C), 135.20 (C), 133.43 (C), 129.94 (CH), 129.12 (C), 126.72 (C), 124.38 (CH), 123.89 (CH), 120.90 (CH), 113.66 (CH), 112.84 (CH), 106.77 (CH), 60.61 (CH2), 50.18 (CH2), 46.12 (CH2), 36.50 (CH3), 17.79 (CH3), 13.63 (CH3), 13.43 (CH3); HRESIMS m/z 348.2055 [M+H]+ (calcd for C22H26N3O, 348.2070).

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, 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Duozhi; Zhang, Heng; Jing, Chenxu; He, Xiaoli; Yang, Bijuan; Cai, Jieyun; Zhou, Yunfu; Song, Xiaoming; Li, Lin; Hao, Xiaojiang; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1491 – 1499;,
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. 149978-43-8, name is 2-Methyl-5-trifluoromethyl-2H-pyrazol-3-ylamine, A new synthetic method of this compound is introduced below., Safety of 2-Methyl-5-trifluoromethyl-2H-pyrazol-3-ylamine

EXAMPLES EXAMPLE 1 5-(2-chloro-6-fluorophenyl)-N-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-pyrazole-3-carboxamide [0112] Compound of Preparation 3 (100 mg, 0.42 mmol) and 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (76 mg, 0.46 mmol) were dissolved in 1.5 mL DMF. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride 98% (62 mg, 0.46 mmol) and 1-Hydroxybenzotriazole hydrate (88 mg, 0.46 mmol) were added and the mixture was stirred at room temperature for 7 days. Dichloromethane was added and the organic phase was washed with water two times, saturated aqueous NaHCO3 solution and brine, dried over MgSO4 and evaporated under reduced pressure and the residue was purified using the Isolera purification (diethyl ether – hexane gradient, 0:100 rising to 100:0) to give 54 mg (0.13 mmol, 33%) of the title compound as a white solid. LRMS (m/z): 388 (M+1)+. 1 H NMR (300 MHz, CHLOROFORM-d) d ppm 3.90 (3 H, s), 6.69 (1 H, s), 7.11 – 7.23 (1 H, m), 7.33 – 7.45 (2 H, m), 8.69 (1 H, br. s)

The synthetic route of 149978-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; GONZALEZ RODRIGUEZ, JACOB; VIDAL JUAN, BERNAT; GUAL ROIG, SILVIA; EP2848615; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 150712-24-6, name is 5-Benzyl-1H-pyrazol-3-amine, molecular formula is C10H11N3, 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. Product Details of 150712-24-6

The solution of 2, 4,5-trichloropyrimidine (0.150 g, 0.82 mmol), 5-benzyl-2H-pyrazol- 3-ylamine (Method 27; 0.129 g, 0.74 mmol), and triethylamine (0.155 ml, 1.12 mmol) in EtOH (5 ml) was heated to55 C for 5 hours and then stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The resulted yellow solid was stirred in hexanes: ether solution (1: 1), collected by filtration, and then recrystallized from DCM to give the title compound (0.212 g,89%).’H NMR (400 MHz, CDC13)6 4.10 (d, J= 15.2 Hz, 2 H), 6.89 (s, 1 H), 7.27-7. 37(m, 5 H), 8. 28 (s, 1 H). MS: Calcd.: 319; Found:[M+H] + 320

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150712-24-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/49033; (2005); 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 1904-24-1 as follows. Safety of 3-Amino-5-ethylpyrazole

A. 4-(2,4-dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazine A mixture of 3-amino-5-ethylpyrazole (10.3 g, 39.3 mmol) and N-(1-(methylthio)ethylidene)-2,4-dichloro-benzamide (4.0 g, 35.7 mmol) in anhydrous dioxan (20 mL) was stirred at reflux temperatrue under a nitrogen atmosphere for 16 h. After being cooled to ambient temperature, the reaction mix was concentrated in vacuo and the residue was treated with dichloromethane. The resulting supsension was filtered and the filtrate was concentrated in vacuo to afford an oil (1.5 g, 14% yield): NMR (CDCl3, 300 MHz): delta 7.62 (d, 1H, J=8), 7.59 (d, 1H, J=2), 7.45 (dd, 1H, J=8,2), 6.42 (s, 1H), 2.82 (q, 2H, J=8), 2.73 (s, 3H), 1.30 (t, 3H, J=8).

According to the analysis of related databases, 1904-24-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilligan, Paul J.; Wilde, Richard G.; US2002/147338; (2002); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1031351-95-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1031351-95-7 name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 2: To a solution of the chloro-phosphonium salt (2.9 g, 5.95 mmol) in dry THF (20 mL) at – 78 0C was added LiHMDS (6.54 mL, 6.54 mmol) and the resulting mixture stirred at -78 0C for 1 h. The mixture was then warmed up to room temperature and a solution of lH-pyrazole-5- carboxylic acid, 3-formyl-l -methyl-methyl ester (1.0 g, 5.95 mmol) in dry THF (15 mL) was added and the resulting mixture stirred for 2 h. Saturated aqueous ammonium chloride (15 mL) was added and the resulting mixture extracted with ethyl acetate (2 x 40 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate 1 :0 to 9:1) afforded, two products, 5-{(Z)-2-[3-(4- fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl} -2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (400 mg) and ethyl 5-{(E)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2- methyl-2H-pyrazole-3-carboxylic acid methyl ester (2.15 g) as off white solids.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127975; (2010); 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. 304693-70-7, name is 1-(2-Methoxyethyl)-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 304693-70-7

To a solution of Intermediate 47 (300 mg, 0.44 mmol) in dichloromethane (5 mL) was added intermediate 50 (80.0 mg, 0.530 mmol) and NaBH(OAc)3 (186 mg, (0941) 0.880 mmol). After stirring at room temperature overnight, the mixture was concentrated to give a residue which was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19* 150mm lOum, Mobile Phase A: H20 (0.1%NH4OH), B: ACN) to yield Compound 97 (53.0 mg, 24.6% yield) as yellow oil. (0942) NMR CDCI3 (400 MHz): delta 8.42 (s, 1H), 7.42 (s, 1H), 7.38 (s, 2H), 4.26 (t, J= 5.2 Hz, 2H), 3.91-3.83 (m, 3H), 3.75-3.73 (m, 3H), 3.64 (q, J= 10.4 Hz, 2H), 3.43 (s, 2H), 3.33 (s, 3H), 2.54-2.49 (m, 4H), 2.37-2.32 (m, 2H), 1.86-1.80 (m, 1H), 1.70-1.63 (s, 1H).

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 304693-70-7.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron Nathaniel; (161 pag.)WO2018/50684; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 40711-33-9, name is Ethyl 5-oxo-2,5-dihydro-1H-pyrazole-3-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 40711-33-9, Application In Synthesis of Ethyl 5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate

To a suspension of ethyl 5-oxo-2,5-dihydro-1 H-pyrazole-3-carboxylate (1.5 g, prepared with an analogous procedure to that described in Preparation 1 ) and Na2CO3 (1.22 g) in dry DMF (20 ml_), [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (1.11 ml.) was added drop wise and the mixture was stirred at 60 0C overnight. The reaction mixture was cooled down to rt and filtered to remove the Na2CO3. The filtrate was diluted with DMF and Na2CO3 (1.22g) and [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (2.1 ml.) were added and the mixture was stirred at 60 0C for additional 36h. After cooling, the mixture was diluted with Et2O, washed with chilly water, dried, filtered and evaporated under reduced pressure. The crude was dissolved in DCM (15 ml.) and 2,6-lutidine (1.08 ml.) and [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (0.86 ml.) were added at 0 0C and the mixture was stirred at rt for 1 h. The mixture was diluted in DCM, washed with NaHCO3sat and then with HCI 0.25N. The organic layer was dried and the solvent evaporated under reduced pressure. The crude was purified by flash chromatography on silica column eluting with Cy/AcOEt with a gradient of Cy from 100% to 80% to give the title compound as colourless oil (0.63 g).MS (m/z): 315 [MH]+.

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; GLAXO GROUP LIMITED; WO2009/130232; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 128694-63-3,Some common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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.

Step 1: l-Methyl-3-(trifluoromethyl)-lH-pyrazol-5-yl] methanol Borane (1M in THF; 9.0 mL, 9.0 mmol) was added to a solution of l-methyl-5- (trifluoromethyl)pyrazole-3-carboxylic acid (350 mg, 1.8 mmol) in THF (10 mL) at rt. The mixture was stirred was stirred for 3 hours. It was then cooled to 0 C and quenched with water. The mixture was extracted with EtOAc (3x) and the combined organic layers were washed with brine, dried over Na2SC>4, filtered, and concentrated. The residue was purified on silica gel to afford [l-methyl-3-(trifluoromethyl)- lH-pyrazol-5-yi]methanol (188 mg; 58%) as a colorless oil. LCMS (FA): m/z = 18l (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 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, its application will become more common.

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