Category: 1192-21-8

Application of 1192-21-8, The chemical industry reduces the impact on the environment during synthesis 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, I believe this compound will play a more active role in future production and life.

3rd Generation BrettPhos precatalyst (12.42 mg, 0.01 mmol) was added to (5)-2-(2-chloro- 5-methylpyrimidin-4-yl)-6-methyl-7-((6-(trifluoromethyl)pyrimidm dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Intermediate 87; 120 mg, 0.27 mmol), 1-methyl- lH-pyrazol-5-amine (66.5 mg, 0.69 mmol) and CS2CO3 (179 mg, 0.55 mmol) in 1,4- dioxane (4mL) 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 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-((6-(trifluoromethyl)pyrimidin-4-yl)methyl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Example 32; 60 mg, 43.9percent) as a white solid. H NMR (300 MHz, DMSO) delta 1.25 (d, 3H), 3.71 (s, 3H), 4.14 – 4.21 (m, 1H), 4.34 – 4.46 (m, 1H), 4.56 – 4.71 (m, 2H), 5.27 (d, 1H), 6.32 (d, 1H), 7.35 (d, 1H), 7.98 (s, 1H), 8.13 (d, 1H), 8.34 (s, 1H), 9.24 (s, 1H), 9.41 (s, 1H). m/z (ES+), [M+H]+ = 499.

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, 1-Methyl-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

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., Quality Control of 1-Methyl-1H-pyrazol-5-amine

Example 1.26; Preparation of (4′-Fluoro-biphenyl-4-yI)-(2-methyl-2Eta-pyrazol-3-yl)-amine (Compound35). A 20-mL scintillation vial was charged with 4′-bromo-4-fluoro-biphenyl (251.1 mg, 1 mmol), 3 -amino-2 -methyl pyrazole (97.1 mg, 1 mmol), sodium terf-butoxide (134.5 mg, 1.4 , mmol), tris(dibenzylideneacetone)dipalladium(0) (45.8 mg, 0.05 mmol), BINuAP (62.3 mg, 0.1 mmol) and toluene (2 mL) under nitrogen atmosphere. The reaction mixture was heated at 800C for 48 hours. It was then allowed to cool to room temperature, taken up in ether/ethyl acetate, filtered and concentrated. The crude material was subjected to column chromatography on silica gel (Biotage, eluent hexanes/ethyl acetate 70/30) to afford Compound 35 as a yellow solid. LCMS m/z (percent) = 268 (M+H, 100).

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

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. Formula: C4H7N3

1-Methyl-1H-pyrazol-5-amine (4.85 g, 49.9 mmol) and diethylethoxymethylenemalonate (10 mL, 50 mmol) were heated at110 C for 1.5 h. The ethanol by-product was removed by evaporationunder reduced pressure. Phosphoryl trichloride (12.1 mL,130 mmol) was added and the mixture was heated at 110 C for3.5 h. The mixture was cooled to room temperature and MeCN(5 mL) was added, and then the solution was further cooled downto 10 C. Water (80 mL) was added slowly maintaining the temperaturebelow 10 C and the suspension was stirred at ambient temperatureovernight. The resultant solid was collected by filtration,washed with minimum amount of water and dried under reducedpressure to afford the title compound (6.7 g, 54percent) as a white solid;1H NMR (400 MHz, DMSO-d6) d = 8.96 (s, 1H), 8.40 (s, 1H), 4.38 (q,J = 7.0 Hz, 2H), 4.10 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H); 13C NMR(101 MHz, DMSO-d6) d = 163.6, 151.0, 150.7, 137.8, 132.2, 118.0,115.1, 61.5, 34.2, 14.0. LCMS (Method A, UV, ES): RT = 1.00 min,[M+H]+ = 240, 242, 97percent purity. These data were in agreement withthose reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1192-21-8, its application will become more common.

Electric Literature of 1192-21-8, 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.

Step 1: A clean 100 L cylindrical reaction vessel was charged with THF (13 kg) then (S)-1-(2-((tert-butyldimethylsilyl)oxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one (I, 5 kg) and 1-methyl-1H-pyrazol-5-amine (1.1 kg) were added sequentially with medium agitation followed by THF (18 kg). The mixture was cooled to ?35¡ã C. and to the resulting thin slurry was added slowly a THF solution of LiHMDS (17.4 kg, 1.0 M) at a rate that maintained the internal temperature below ?25¡ã C. After the addition was completed, the reaction was held between ?35 and ?25¡ã C. for 20 min and monitored by HPLC. If the HPLC result indicated ?98.5percent conversion, additional LiHMDS (0.34 kg, 1.0 M, 0.05 mol percent) was added slowly at ?35¡ã C. The reaction was quenched slowly at the same temperature with H3PO4 solution (4.4 kg of 85percent H3PO4 and 15 kg of water) and the internal temperature was kept below 30¡ã C. The reaction was diluted with EtOAc (18 kg) and the phases separated, the organic layer was washed with H3PO4 solution (1.1 kg of 85percent H3PO4 and 12 kg of water) followed by a second H3PO4wash (0.55 kg of 85percent H3PO4 and 12 kg of water). If 1-methyl-1H-pyrazol-5-remained, the organic layer was washed again with H3PO4 solution (0.55 kg of 85percent H3PO4 and 12 kg of water). Finally the organic layer was washed sequentially with water (20 kg) and a NaCl and NaHCO3 solution (2 kg of NaCl, 0.35 kg of NaHCO3 and 10 kg of water). After the phase separation, residue water in organic solution was removed through an azeotropic distillation with EtOAc to <0.5percent (by KF) and then solution was concentrated to 20-30 L under a vacuum below 50¡ã C. The solvent was then swapped to MeOH using 35 kg of MeOH and then concentrated to between 20 and 30 L for the next step. The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazol-5-amine. I believe this compound will play a more active role in future production and life.

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, 1192-21-8

Example 194; N-(1-Methyl-1H-pyrazol-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 2,2,2-Trichloroethyl (1-methyl-1H-pyrazol-5-yl)carbamate; To a solution of 1-methyl-1H-pyrazole-5-amine (1.00 g, 10.3 mmol) and pyridine (1.01 ml, 12.4 mmol) in tetrahydrofuran (34 ml) was added 2,2,2-trichloroethyl chloroformate (1.71 ml, 12.4 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1) to obtain the desired product (1.43 g, 50.8percent) as an oil. 1H-NMR (CDCl3) delta; 3.78 (3H, s), 4.83 (2H, s), 6.21 (1H, br s), 7.15 (1H, br s), 7.43 – 7.44 (1H, m).

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, 1-Methyl-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

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

Heat a solution of 2,4-dichloropyridine (15.3 g, 103 mmol), L-methyi5 aTninopyrazole (ii g, 113 mmoi), cesium carbonate (6 g, 10 nimol) and tris(dibenzyiideneacetone)dipaiiadium(0) (4.7 g, 5 mmoi) in 1 ,4dioxane (750 niL) in asealed vessel at 75 ¡ãC overnight. Cool the reaction to room temperature and dilute with water (1.5 L). Extract the mixture with three portions DCM, Filter the aqueous layer to remove solids and extract the filtrate with two portions EtOAc. Combine all organic extracts, dry over magnesium sulfate, filter and concentrate the filtrate. Purify the residue by silica gel column chromatography by loading the product onto a 260 g pre-coiumn andeluting the pre-colunin onto a 750 g column with a gradient from 1-5percent MeOH in DCM to give the title compound 16.8 g (78percent). MS (m/z): 209 (M+i),

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

1192-21-8, The chemical industry reduces the impact on the environment during synthesis 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, I believe this compound will play a more active role in future production and life.

3rd Generation BrettPhos precatalyst (11.90 mg, 0.01 mmol) was added to 1 -methyl- 1H- pyrazol-5 -amine (87 mg, 0.89 mmol), Cs2C03 (291 mg, 0.89 mmol) and (5)-2-(2-chloro-5- methylpyrimidin-4-yl)-6-methyl-7-((6-(trifluoromethyl)pyridin-2-yl)methyl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Intermediate 77; 130mg, 0.30 mmol) in 1,4- dioxane (5 mL) under nitrogen. The resulting mixture was stirred at 100 ¡ãC for 4 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, product containing fraction were evaporated to afford a solid. This solid 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 0.1percent Formic acid) 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-((6- (trifluoromethyl)pyridin-2-yl)methyl)-6,7-dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Example 27; 100 mg, 67.5percent) as a white solid. lH NMR (300 MHz, DMSO, 23 ¡ãC) delta 1.20 (3H, d), 2.56 (3H, s), 3.70 (3H, s), 4.05-4.18 (1H, m), 4.37-4.41 (1H, m), 451-4.60 (2H, m),5.212 (1H, d), 6.30 (1H, d), 7.34 (1H, d), 7.76-7.83 (2H, m), 7.96 (1H, s), 8.06-8.11 (1H, m), 8.32 (1H, s). m/z (ES+), [M+H]+ = 498.

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

1192-21-8, 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.

[00180] Step 3: To a solution of dioxane (150 mL) was added 2-chloro-4-(2- fluoropyridin-4-yl)pyrimidine (15.0 g, 72.1 mmol), 1 -methyl- lH-pyrazol-5 -amine (7.6 g, 79.3 mmol), cesium carbonate (35.3 g, 108.0 mmol), Pd2(dba)3 (6.6 g, 7.2 mmol) and xantphos (8.3 g, 14.4 mmol). The mixture was heated at 80 ¡ãC under a nitrogen atmosphere for 2 hours. TLC (PE:EtOAc = 5: 1) indicated that the starting material was consumed. The mixture was cooled to room temperature and filtered through a bed of Celite?. The filtrate was then partitioned between EtOAc (200 mL) and water (100 mL). After separation, the organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, concentrated and then purified by column chromatography on silica gel (PErEtOAc = 10: 1 to about 1 : 1) to provide 4-(2-fluoropyridin-4-yl)-N-(l -methyl- lH-pyrazol-5-yl)pyrimidin-2- amine (14.5 g, 74percent) as a solid.

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1192-21-8, 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 1192-21-8 as follows.

Sparge a solution of 2-(2-chloro-4-pyridyi)-5-2-cyclopropoxy)ethyl]-6,6- dimethyi-thieno[2,3-c]pyrrol-4-one (13.9 g, 121 mmol), i-methyi-5-aminopyrazole (ii g, 113 rnrnoi), and sodium tert-butoxide (6.5 g, 68 mrnol) in toluene (150 mL) with nitrogen for 15 minutes. Treat the resulting mixture with (R)- I -[(Sp)-2- (dicyciohexyiphosphino)ferrocenyiiethyldi-tert-hutylphosphine (200 mg, 0.36 mmol) andbis(tri-o-toiyiphosphine)paliadium(0) (250 mg, 0.35 mmoi), Heat the reaction mixture to reflux for one hour. Cool the reaction to room temperature and dilute with EtOAc (500 mL), Wash the organic solution with water (300 mL), Separate and concentrate the organic phase under reduced pressure, Dissolve the residue inDCM (150 mL) and treat the solution with SILIAMETS Thiol (40 g, I .28 mrnol/g, 40-63 micron) and stir the mixture for four hours, Filter to remove the solid and concentrate the filtrate under reduced pressure to give the title compound I LI g (86%). MS (ink): 424 (M+i).

According to the analysis of related databases, 1-Methyl-1H-pyrazol-5-amine, the application of this compound in the production field has become more and more popular.

1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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. 1192-21-8

(R)-2-(2-Chloro-5-methylpyrimidin-4-yl)-6-m yl)methyl)-6,7-dihydroimidazo[l ,2-a]pyrazin-8(5H)-one (Intermediate 91 ; 187 mg, 0.43 mmol), 1 -methyl- lH-pyrazol-5-amine (104 mg, 1.07 mmol),Cs2C03 (279 mg, 0.86 mmol) and 2nd Generation XantPhos precatalyst (38.0 mg, 0.04 mmol) in 1 ,4-dioxane (5 mL) was stirred under an atmosphere of nitrogen at 1 10 ¡ãC for 16 hours. The solvent was removed by distillation under vacuum. The crude product was purified by flash silica chromatography, elution gradient 3 to 5percent MeOH in DCM. The product was further purified by preparative HPLC (XSelect CSH Prep C 18 OBD column, 5mu silica, 19 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.01percent NH4HCO3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford (i?)-6-methyl-2-(5-methyl-2-((l-methyl-lH-pyrazol-5- yl)amino)pyrimidin-4-yl)-7-((6-(trifluoromethyl)pyridin-2-yl)methyl)-6,7- dihydroimidazo[l ,2-a]pyrazin-8(5H)-one (1 12 mg, 52.6percent) as a white solid. lH NMR (400 MHz, DMSO, 20.9 ¡ãC) delta 1.22 (3H, d), 2.52 (3H, s), 3.35 (1H, s), 3.71 (3H, s), 4.13 (1H, ddd), 4.40 (IH, dd), 4.51 – 4.63 (2H, m), 5.22 (IH, d), 6.31 (IH, d), 7.34 (IH, d), 7.78 (IH, d), 7.84 (IH, d), 7.97 (IH, s), 8.10 (IH, t), 8.33 (IH, d), 9.24 (IH, s). m/z (ES+), [M+H]+ = 498.

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