Tag: M.W=0-100

Application of 1192-21-8, These common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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.

To a mixture of (i?)-2-(2-chloro-5-methylpyrimidin-4-yl)-7-(3,4-difluorobenzyl)-6- (methoxymethyl)-6,7-dihydroimidazo[l ,2-a]pyrazin-8(5H)-one (Intermediate 62; 104.7 g, 225.64 mmol), 1 -methyl- lH-pyrazol-5-amine (33.5 g, 338.47 mmol) in 2-methyl tetrahydrofuran (1200 mL) and CS2CO3 (147 g, 451.29 mmol) in water (120 mL) were added 2′-(dicyclohexylphosphanyl)-N,N-dimethyl-[l, -biphenyl]-2-amine (7.10 g, 18.05 mmol) and Pd2(dba)3 (8.27 g, 9.03 mmol) at 25 °C under nitrogen. The resulting mixture was degassed 3 times under nitrogen and then stirred at 70 °C for 24 hours. The reaction mixture was cooled to room temperature and the layers were separated. The organic layer was washed successively with water (500 mL), aqueous citric acid (IN, 600 mL) and water (200 mL). Silicycle (Si-SH, 150 g) was added to the organic layer at 40 °C and stirred for 20 hours. After filtration the filtrate was concentrated and the residue was purified by SFC chromatography using a Kromasil DIOL column, elution gradient 25percent EtOH/NH3 100/0.5 in C02, 140 bar. Pure fractions were evaporated to dryness to afford (i?)-7-(3,4- difluorobenzyl)-6-(methoxymethyl)-2-(5-methyl-2-((l -methyl- lH-pyrazol-5- yl)amino)pyrimidin-4-yl)-6,7-dihydroimidazo[l ,2-a]pyrazin-8(5H)-one (Example 18; 72.6 g, 65percent) as a solid. NMR (500 MHz, DMSO) delta 2.51 (3H, s), 3.17 (3H, s), 3.30 (1H, dd), 3.39 (1H, dd), 3.69 (3H, s), 4.03 (1H, dtd), 4.38 (1H, d), 4.44 (1H, dd), 4.51 (1H, dd), 5.08 (1H, d), 6.30 (1H, d), 7.22 – 7.28 (1H, m), 7.33 (1H, d), 7.41 (1H, dt), 7.47 (1H, ddd), 7.93 (1H, s), 8.31 (1H, s), 9.21 (1H, s). m/z (ES+), [M+H]+ = 495

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

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; SWALLOW, Steven; GRAHAM, Mark, Andrew; DOBSON, Andrew, Hornby; MCCABE, James, Francis; (223 pag.)WO2017/80979; (2017); A1;,
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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. 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 3-Methyl-1H-pyrazol-5-ol

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95%, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol %) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

The synthetic route of 132712-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
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Synthetic Route of 1072-68-0,Some common heterocyclic compound, 1072-68-0, name is 1,4-Dimethylpyrazole, molecular formula is C5H8N2, 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 1,4-dimethyl-pyrazole (10 g, 104.03 mmol) in DMF (150 mL) was added NIS (21.06 g, 93.63 mmol) in one portion at 25 C under ?. The mixture was stirred at 60 C for 12 h. The mixture was poured into ice-water (300 mL) and stirred for 5 min. The aqueous phase was extracted with MTBE (3 chi 300 mL). The combined organic phase was washed with brine (3 chi 200 mL), dried over anhydrous Na2SO/j, filtered and concentrated under reduced pre ssure . The re sidue was purified by silica gel column chromatography (PE : EtO Ac= 10 : 1 – 1 : 1 ) to give 3-iodo- 1,4-dimethyl-pyrazole as a brown solid. lH NMR (400 MHz, CDC33): delta ppm 7.05 (s, 1 H), 3.86 (s. 3 1 1). 1.98 (s, 3H).

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

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
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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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., COA of Formula: C4H7N3

3rd Generation BrettPhos precatalyst (31.1 mg, 0.03 mmol) was added to (iS)-2-(2-chloro- 5-methylpyrimidin-4-yl)-6-methyl-7-((4-(trifluoromethyl)pyridin-2-yl)mdihydroimidazo[l,2-a]pyrazin-8(5H)-one (Intermediate 80; 300 mg, 0.69 mmol), 1-methyl- lH-pyrazol-5-amine (167 mg, 1.72 mmol) and CS2CO3 (448 mg, 1.37 mmol) in 1,4- dioxane (8 mL) at 25°C under nitrogen. The resulting mixture was stirred at 100 °C for 8 hours. The solvent was then removed under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0 to 6percent MeOH in DCM. Compound containing fractions were evaporated to dryness to afford a yellow residue. This residue was purified further by preparative HPLC (XSelect CSH Prep C18 OBD column, 5mu silica, 19 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.03percent NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford (5)-6-methyl-2-(5-methyl-2-((l-methyl- lH-pyrazol-5-yl)amino)pyrimidin-4-yl)-7-((4-(trifluoromethyl)pyridin-2-yl)methyl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Example 28; 141 mg, 41.3percent) as a white solid. ^ NMR ^OO MHz, DMSO, 20 °C) delta 1.21 (3H, d), 2.52 (3H, s), 3.71 (3H, s), 4.13 (IH, dd), 4.37 (IH, dd), 4.52 (IH, dd), 4.58 (IH, d), 5.26 (IH, d), 6.31 (IH, d), 7.34 (IH, d), 7.71 (IH, d), 7.82 (IH, s), 7.95 (IH, s), 8.33 (IH, s), 8.84 (IH, d), 9.24 (IH, s). m/z (ES+), [M+H]+ = 498.

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; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; SWALLOW, Steven; GRAHAM, Mark, Andrew; DOBSON, Andrew, Hornby; MCCABE, James, Francis; (223 pag.)WO2017/80979; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 67-51-6, 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. 67-51-6, name is 3,5-Dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: SOCl2 (5 mL) was added to a round-bottom flask, and then 1a-i(1.0 mmol) and a catalytic amount of DMF (0.1 mmol) were added. Themixture was heated to reflux for 4 h (reaction monitored by HPLC),then excess SOCl2 was evaporated under reduced pressure. The residuewas dispersed in H2O (200 mL) and extracted with AcOEt. The organicphase was separated, dried, and concentrated. It was then purified byflash column chromatography (eluent: ethyl acetate/petroleum ether,1 : 10 v/v) to afford 2a-i.

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

Reference:
Article; Li, Yi; Liu, Yuanyuan; Xu, Guanghui; Chen, Kai; He, Guangke; Huang, Bin; Journal of Chemical Research; vol. 38; 11; (2014); p. 658 – 661;,
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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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 1H-Pyrazole-4-carbonitrile

To a suspension of K2CO3 (63 mg, 0.46 mmol) in THF (10 mL) was added 4-cyanopyrazole (43 mg, 0.46 mmol) and compound SB-W (100 mg, 0.23 mmol). After stirring at room temperature for 15h, the reaction mixture was poured into 5 mL H20 and extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine (2 x 10 mL), dried over sodium sulfate,filtered and concentrated under vacuum. The residue was purified by reverse-phase prep-HPLC to afford SB-9 as a white solid (43.5 mg, 0.095 mmol, 41.7%). 1HNMR (500 MHz, CDC13) delta (ppm7.86 (IH, s), 7.82 (IH, s), 5.01 (IH, AB), 4.91 (IH, AB), 3.53 (2H, q), 3.22 (2H, s), 2.61 (IH, t), 0.67 (3H, s), 0.67-2.25 (24H, m). LCMS: Rt = 2.37 mm. m/z = 454.4 [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; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); A1;,
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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. 28466-26-4, name is 4-Aminopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H5N3

Imine (I1) A solution of 4-aminopyrazole (10) (10.5 g, 126 mmol), ethylacetoacetate (18.0 g, 140 mmol, 1.05 eq.) and a catalytic amount of para-toluenesulfonic acid monohydrate (1.3 g, 6.65 mmol, 5%) in 100 mL of benzene was refluxed with a Dean-Stark trap for about 1 hour. The end of reaction checked by TLC (Ethylacetate/Hexane 1/1, 4-aminopyrazole Rf=0.1, imine Rf=0.5, UV active, brown after overnight). Solvents were removed under vacuum and the imine was purified by running through a short silica chromatography column to give the desired product (11) as a tan solid (22.4 g, 125 mmol, 91%). GC/MS: m/z=195 (100%).

The synthetic route of 28466-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Neurocrine Biosciences, Inc.; US6531475; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 35277-02-2, The chemical industry reduces the impact on the environment during synthesis 35277-02-2, name is 4-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-(4-fluoro- lH-pyrazol- l-yl)propanamide (C14H10F4N4O) (0837) 1029 (0838) [00384] To a solution of 4-fluoro-pyrazole (0.20 g, 0.0023237 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.28 g, 0.0069711 mol). After addition, the resulting mixture was stirred for 3 h. 3- Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)propanamide (1029a, 0.75 g, 0.0023237 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using DCM and methanol (19: 1) as eluent to afford 0.75 mg (10%) of the titled compound as white solid. (0839) [00385] Compound 1029 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.81 (s, 1H, NH), 8.25 (d, = 2.4 Hz, 1H, ArH), 8.10 (dd, = 8.8 Hz, = 2.4 Hz, 1H, ArH), 7.95 (d, = 8.8 Hz, 1H, ArH), 7.88 (s, 1H, Pyrazole-H), 7.46 (s, 1H, Pyrazole-H), 4.35 (t, J = 6.0 Hz, 2H, CH2), 2.79 (t, J = 6.0 Hz, 2H, CH2); Mass (ESI, Negative): 325.03 [M-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, 4-Fluoro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3920-50-1,Some common heterocyclic compound, 3920-50-1, name is Pyrazole-3-carboxaldehyde, molecular formula is C4H4N2O, 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.

1.04 g (15 mmol) of hydroxylamine hydrochloride, 1.23 g (15 mmol) of sodium acetate and 40 ml of ethanol were added to a 100 ml three-necked flask, and 0.96 g (10 mmol) of 3-formalpyrazole was added thereto with stirring.The temperature was raised to 60 C and the reaction was carried out for 3 h. After the reaction, the milky white turbid liquid was obtained and cooled to room temperature.filter,The filtrate was evaporated to give an oily viscous solid, which was dissolved in 50 ml of water.Extract 50 times with 50 ml of ethyl acetate.The organic phase was dried over anhydrous sodium sulfate and filtered.The filtrate was evaporated to dryness to give a pale yellow viscous solid 0.99 g.The yield was 89.5%.

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

Reference:
Patent; Xi’an Modern Chemical Institute; Zhang Yiying; Li Purui; Zhou Cheng; Wang Wei; Sun Chenghui; (7 pag.)CN109438353; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 69843-13-6, 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. 69843-13-6, name is 1-Methyl-1H-pyrazol-4-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 34 6-[3-(4-Chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-N-(l-methyl-lH-pyrazol-4-yl)- nicotinamide To a solution of 6-[3-(4-chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (224 mg, 0.65 mmol) and 1 -methyl- lH-pyrazol-4-ylamine (0.65 mmol) in THF (6 mL) at 0 C were added 1-hydroxybenzotriazole hydrate ( 100.8 mg, 0.65 mmol), N-ethyldiisopropylamine (281.7 mu?, 1.613 mmol) and N-(3-dimethylaminopropy)-N -ethylcarbodiimidazole hydrochloride (126.2 mg, 0.65 mmol). The resulting reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (Si02, heptane:ethyl acetate = 3: 1 to 1:4) afforded the title compound (201 mg, 73%) which was obtained as a white solid. MS: m/e = 424.2 [M+H]+.

The synthetic route of 1-Methyl-1H-pyrazol-4-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; HANLON, Steven Paul; HILDBRAND, Stefan; IDING, Hans; THOMAS, Andrew; WALDMEIER, Pius; WO2013/57123; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics