Category: 1192-21-8

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., Safety of 1-Methyl-1H-pyrazol-5-amine

(S)-7-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methyl-2H- 1 ,2,3-triazol-4- yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (190 mg, 0.51 mmol), 1-methyl- 1H-pyrazol-5-amine (54.6 mg, 0.56 mmol), cesium carbonate (333 mg, 1.02 mmol) and BrettPhos 3rd generation pre-catalyst (23.16 mg, 0.03 mmol) were suspended in tertbutanol (6mL) and de-gassed for 10 minutes. The reaction was heated to 80 °C for 18hours under nitrogen. Reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (25 mL), dried over sodium sulfate and concentrated in vacuo to give a yellow solid. The crude product was dissolved in DMSO (5 mL), filtered and purified by preparative HPLC (Waters XBridge Prep C18 OBD column, Sji silica, 30 mm diameter, 100 mm length),using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents.Fractions containing the desired compound were evaporated to dryness to afford (S)-3-methyl-7-(5 -methyl-2-(( 1-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methyl-2H- 1,2,3 -triazol-4-yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (102 mg, 46.2percent) as a white solid. ?H NMR (500 MHz, DMSO, 30 °C) 1.15 (3H, d), 2.33 (3H, s), 3.70(3H, s), 3.9 – 4.01 (1H, m), 4.12 (3H, d), 4.14 – 4.32 (2H, m), 4.35 (1H, d), 5.08 (1H, d),6.27 (1H, d), 7.26 (1H, d), 7.34 (1H, d), 7.64 (1H, d), 7.69 (1H, s), 8.24 (1H, s), 9.08 (1H,s). mlz: ES+ [M+H]+ = 433.

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; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

Step 3 Under an atmosphere of nitrogen 1-methyl-1H-pyrazol-5-amine (284.5 mg, 2.93 mmol) was dissolved in THF (17.8 mL) at RT and treated with 1.0M LiHMDS in THF (5.86 mL, 5.86 mmol). The reaction was stirred vigorously for 10 min, and then 90 (280 mg, 1.4647 mmol) was added as a solid in one portion. The 100 mL round bottom reaction flask was equipped with a water cooled condenser and heated to 80° C. The reaction was 30percent complete after 3.5 h, so additional 1.0M LiHMDS was added (8.86 mL, total: 14.72 mL, 14.72 mmol), and the reaction heated at 80° C. for another 2.5 hours (total time at 80° C.=6 h). The reaction mixture was diluted with water (20 mL), transferred to a separatory funnel and washed with DCM (4*30 mL). The DCM washings were combined, and the aqueous layer was neutralized via the addition 1.26 mL of 11.6 M aqueous HCl. The resulting precipitate was collected via vacuum filtration to afford 373 mg (94percent) of 3-(1-methyl-1H-pyrazol-5-ylamino)isoquinoline-6-carboxylic acid (92), which was used without any further purification.

Statistics shows that 1-Methyl-1H-pyrazol-5-amine is playing an increasingly important role. we look forward to future research findings about 1192-21-8.

Reference:
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-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 1192-21-8, category: pyrazoles-derivatives

General procedure: To a mixture of corresponding 12 (0.14 mmol) and corresponding amine (0.14 mmol) in 1, 4-dioxane (3 mL) was added Pd(OAc)2 (3.00 mg, 0.01 mmol), XantPhos (35.00 mg, 0.06 mmol) and Cs2CO3 (68.00 mg, 0.21 mml). The mixture were heated to 100 oC for 12 h under N2 atmosphere. After completion, the mixture were cooled to room temperature and purification by column chromatography on silica gel to give the corresponding products.

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

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-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 1192-21-8, Computed Properties of C4H7N3

Step ()N-(2-(5-chloro-2-(l -methyl- lH-pyrazol-5-ylamino)pyrimidin-4-ylamino)-5- methoxyphenyl)methanesulfonamideA mixture of N-(2-(2,5-dichloropyrimidin-4-ylamino)-5-methoxyphenyl) methane sulfonamide (2 g, 5.5 mmol, see Example 1 steps (i) and (ii)), l-methyl-lH-pyrazol-5-amine (536 mg, 5.5 mmol), palladium acetate (61 mg, 2.8 mmol), Xantphos (159 mg, 2.7 mmol) and cesium carbonate (1.79 g, 5.5 mmol) in 1,4-dioxane (40 mL) was stirred at 1600C for 2 h in a microwave reactor then concentrated in vacuo. The residue was partitioned between DCM and water and the aqueous layer was extracted three times with DCM. The combined organic layer was washed with brine (5 mL), dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica gel, 0-5% methanol-DCM with 0.1% triethylamine) to afford the title compound (504 mg, 22%).

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

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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-Methyl-1H-pyrazol-5-amine

O-iodobenzoic acid(II)(5.00g, 20.00mmol),1-methyl-1-H-5-aminopyrazole (III) (1.90 g,20.00 mmol), potassium carbonate (5.50 g, 40.00 mmol) and CuI (0.76 g, 4.00 mmol) dissolved in DMF (20.00 ml), temperature controlStir at 100 to 105 C for 8 h.TLC (petroleum ether: ethyl acetate = 1:1) was used to detect the reaction of the starting material II, the heating was stopped, and the mixture was cooled to room temperature.The reaction solution was poured into water (60.00 ml).After stirring for 20 min, the pH of the reaction system was adjusted with 1.00 mol/L HCl, and the pH was 5-6.Precipitating a brown solid, suction filtration, drying,Obtained a brown solid 3.10g,Yield 70%,

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

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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

General procedure B for the synthesis of the final product lb from intermediate E or K In a sealed tube, the bromo-intermediate E or K (0.08 mmole), t-BuONa (0.16 mmole) and the amine (0.16 mmole) were charged. The tube was filled with Argon, dry toluene (1.0 ml) was added and the mixture was stirred for 2 min. Then Pd2(dba)3 (0.0024 mmole) and t-BuXphos (0.016 mmole) were added and the vial was flushed with Argon and stirred for 2 min. The reaction mixture was then heated at 100 °C for 18h. The mixture was concentrated in vacuo and purified by flash chromatography eluting with ethyl acetate/n-heptane. To a solution of the purified product in dichloromethane (0.5ml) was added TFA (0.4 mmole) and the mixture was stirred at room temperature for 30 min. The mixture was diluted with dichloromethane and the organic layer was washed with saturated aqueous NaHC03, dried and evaporated. The crude material was purified by chromatography on NH2-silica using dichloromethane to give the pure final product lb. In case of using intermediate E, the coupling product was deprotected using CF3COOH as described above to give the pure final product lb.Example 36(S)-2-Amino-6-[2-fluoro-5-(2-methyl-2H-pyrazol-3-ylamino)-phenyl]-3,5,5,6-tetramethyl- 5,6-dihydro-3H-pyrimidin-4-oneThe coupling of [(S)-4-(5-bromo-2-fluoro-phenyl)- 1,4,5, 5-tetramethyl-6-oxo- 1,4,5, 6- tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (intermediate E8) and 2-methyl-2H- pyrazol-3-ylamine according to procedure B followed by deprotection yielded the title compound as a pale brown waxy solid. MS (ESI): m/z = 359.2 [M+H]+.

According to the analysis of related databases, 1192-21-8, the application of this compound in the production field has become more and more popular.

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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-pyrazol-5-amine

(3 S)-7-(2-Chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methylpyrimidin-4-yl)methyl)- 3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (122 mg, 0.32 mmol), i-methyl-i H-pyrazol5-amine (37.1 mg, 0.38 mmol) and cesium carbonate (228 mg, 0.70 mmol) were suspended in tert-butanol (2 mL) and de-gassed with nitrogen for 5 minutes, then BrettPhos 3rd generation pre-catalyst (14.44 mg, 0.02 mmol) was added. The reaction was heated to100 °C in the microwave for 1 hour, then allowed to cool to ambient temperature, diluted with DCM (30m1), washed with brine (30m1), separated, dried (MgSO4) and evaporated to afford crude product, which was purified by preparative HPLC (Waters XBridge Prep Ci 8 OBD column, Sji silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents. Fractions containing thedesired compound were evaporated to dryness to afford (3S)-3-methyl-7-(5-methyl-2-((i- methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methylpyrimidin-4-yl)methyl)-3 ,4- dihydropyrrolo[i,2-a]pyrazin-i(2H)-one (67.2 mg, 47.5 percent) as a pale yellow gum. 1H NMR (500 MHz, DMSO, 30 °C) 1.20 (3H, d), 2.34 (3H, s), 2.62 (3H, s), 3.70 (3H, s), 3.97 – 4.05 (iH, m), 4.24 (iH, dd), 4.34 (iH, d), 4.47 (iH, dd), 5.10 (iH, d), 6.27 (iH, d), 7.27 (iH,d), 7.29 (iH, d), 7.34 (iH, d), 7.69 (iH, d), 8.25 (iH, s), 8.63 (iH, d), 9.09 (iH, s). mlz:ES+ [M+H]+ 444.

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 1192-21-8.

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-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 1192-21-8, Safety of 1-Methyl-1H-pyrazol-5-amine

Degas a mixture of 2-(2-chloropyrimidin-4-yl)-6,6-dimethyl-5-(2- morpholinoethyl)thieno[2,3-c]pyrrol-4-one (20.8 g, 52.9 mmol), 2-methylpyrazol-3-amine (5.7 g, 58.2 mmol), cesium carbonate (37.9 g, 116.5 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (2.6 g, 4.5 mmol) and 1,4-dioxane (529 mL) with nitrogen for 10 minutes. Add tris(dibenzylideneacetone)dipalladium(0) (2.4 g, 2.6 mmol) and heat the mixture to 85 C for four hours. Cool the mixture to room temperature and filter the mixture through filter paper. Concentrate the filtrate under reduced pressure. Repeat the reaction starting with 8 g of 2-(2-chloropyrimidin-4-yl)-6,6- dimethyl-5-(2-morpholinoethyl)thieno[2,3-c]pyrrol-4-one and combine the two residues. Purify the residue by silica gel column chromatography (330 g) eluting with a gradient from 5-25% MeOH in (10% EtOAc in DCM). Pool the fractions and concentrate under reduced pressure. Re-purify the residue by silica gel column chromatography (330 g) eluting with a gradient from 5-25% MeOH in 10% EtOAc in DCM. Pool the fractions and concentrate under reduced pressure. Dissolve the residue in DCM (400 mL) and then add acetone (1 L). Slowly concentrate the mixture under reduced pressure to approximately 700 mL. Collect the solid by vacuum filtration to give the title compound 14.8 g (48%). MS (m/z): 454 (M+1).

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.

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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1192-21-8

2nd Generation XantPhos precatalyst (26.4 mg, 0.03 mmol) was added to (5)-2-(2,5- dichloropyrimidin-4-yl)-6-methyl-7-((6-methylpyridin-2-yl)methyl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Intermediate 46; 120 mg, 0.30 mmol), 1-methyl- lH-pyrazol-5-amine (72.2 mg, 0.74 mmol) and Cs2C03 (194 mg, 0.60 mmol) in 1,4- dioxane (8 mL) at 25 ¡ãC under nitrogen. The resulting mixture was stirred at 100 ¡ãC 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. Pure fractions were evaporated to dryness to afford a yellow residue. This residue was further purified by preparative HPLC (XSelect CSH Prep CI 8 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)-2-(5-chloro-2-((l-methyl-lH-pyrazol-5-yl)amino)pyrimidin-4-yl)-6- methyl-7-((6-methylpyridin-2-yl)methyl)-6,7-dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Example 11; 50 mg, 36.2percent) as a white solid. H NMR (400 MHz, DMSO, 22 ¡ãC) delta 1.19 (3H, d), 2.47 (3H, s), 3.70 (3H, s), 4.08 (IH, d), 4.32 – 4.43 (2H, m), 4.53 (IH, dd), 5.15 (IH, d), 6.31 (IH, d), 7.21 (2H, dd), 7.34 (IH, d), 7.68 (IH, t), 8.21 (IH, s), 8.53 (IH, s), 9.72 (IH, s). m/z (ES+), [M+H]+ = 464

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 1192-21-8.

Related Products of 1192-21-8,Some common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, molecular formula is C4H7N3, 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.

General procedure: Electrolysis was carried out usinga B5-49 direct current source, 0.2 m aqueous NaOH as the supportingelectrolyte, in a glass temperature-controlled (25 ¡ãC) cell (V = 150 ml)with a NiO(OH) anode (S = 48 cm2) prepared by a reported procedure36and a Ti cathode (S = 20 cm2). The supporting electrolyte (100 ml) andamine 1a?e (0.003 mol) were placed into the cell and electrolysis wascarried out at a current of 290 mA. Once a 2 F per mole of the startingamine was passed (Q = 579 C), electrolysis was stopped. The reactionmixture was stirred for more 0.5 h in the absence of current and analyzedby TLC with light petroleum?ethyl acetate (1:1) as the eluent. ConcentratedHCl was then added to the reaction mixture to pH ~ 3 andthe mixture was extracted with CHCl3 (3¡Á50 ml). The extracts werecombined, dried with anhydrous MgSO4 and concentrated in vacuo.Column chromatography on SiO2 with light petroleum?ethyl acetate(10:1) as the eluent gave azopyrazoles 2a?e which were identified usingthe reported characteristics.26,28 The aqueous solution that remainedafter extraction (see above) was concentrated in vacuo and NaOH wasadded with stirring (to pH ~ 10). The nonreacted starting amines 1a?ewere extracted with CHCl3 (3¡Á30 ml) and identified by TLC and 1H NMR.

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-1H-pyrazol-5-amine, its application will become more common.