Category: 285984-25-0

Adding a certain compound to certain chemical reactions, such as: 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-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 285984-25-0, category: pyrazoles-derivatives

To a solution of CDI (510 mg, 3.15 mmol) in dry DCM (6.0 mL) at RT was added Intermediate A1 (722 mg, 3.15 mmol) portionwise over 15 min and the reaction mixture maintained at RT for 20 hr. An aliquot of the resulting solution (840 mu, 0.44 mmol) was added to a solution of Intermediate M1 , (81 mg, 0.21 mmol) in dry DCM (4.0 mL) and the reaction mixture was maintained at RT for 1 day and was then partitioned between saturated aq. NaHC03 (20 mL) and DCM (20 mL). The aq layer was separated and extracted with DCM (20 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 12 g, [1 % NH3 in MeOH] in DCM, 0-10%, gradient elution) to provide the title compound, Example 24, as a white solid (53 mg, 37 %); Rl 5.39 min (Method 1 basic); m/z 640/642 (M+H)+, (ES+); 1H NMR (400 MHz, DMSO-de) delta: 1.27 (9H, s), 2.16 (6H, s), 2.33 (2H, t), 2.34 (3H, s), 3.21 (2H, td), 6.38 (1 H, s), 7.23-7.28 (2H, overlapping m), 7.33-7.37 (3H, overlapping m), 7.41 (2H, m), 8.08 (1 H, d), 8.35 (1 H, d), 8.83 (1 H, br s), 9.17 (1 H, br s), 9.68 (1 H, br s).

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, 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; HARDY, George; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/121366; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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 stirred solution of CDI (223 mg, 1 .38 mmol) in dry DCM (3.5 mL) was added Intermediate A1 (315 mg, 1 .38 mmol) as a solid, portion-wise, over 12 min and the resulting solution maintained at RT for 4 hr. An aliquot of this solution (2.0 mL, 0.79 mmol) was added to a solution of Intermediate G1 , (140 mg, 0.39 mmol) in dry THF (5.0 mL), and the reaction mixture was kept at RT for 17 hr and was then partitioned between saturated aq. NaHC03 (30 mL) and DCM (30 mL). The aq. layer was extracted with DCM (30 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 12 g, [5% MeOH in EtOAc] in isohexane, 0-45%, gradient elution) to afford the title compound, Example 14, as an off white solid (127 mg, 52%); R’ 5.40 min (Method 1 basic); m/z 61 1/613 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) delta: 1 .26 (9H, s), 2.37 (3H, s), 3.37 (3H, s), 4.07 (2H, s), 5.31 (2H, s), 6.34 (1 H, s), 7.18-7.23 (2H, overlapping m), 7.31 -7.34 (2H, overlapping m), 7.38-7.40 (2H, overlapping m), 7.85 (1 H, d), 8.21 (1 H, br s), 8.33 (1 H, dd), 8.60 (1 H, br s), 8.95 (1 H, br s), 10.01 (1 H, br s).

The synthetic route of 285984-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; HARDY, George; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/121366; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-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 285984-25-0, category: pyrazoles-derivatives

Example 127; {[3-(tert-butyl)-l-(4-methylphenyl)pyrazol-5-yl]amino}-N-[(2-{[5-bromo-2-methyl- l-(methylethyl)-6-oxohydropyridin-4-yloxy]methyl}-5- fluorophenyl)methyl]carboxamide; [0337] To a solution of 6-{ [2-(aminomethyl)-4-fluorophenyl]methoxy}-5-bromo- 2-methyl-3-(methylethyl)-3-hydropyrimidin-4-one (0.384g, 1.0 mmol) in dichloromethane (15 mL) and saturated solution Of NaHCO3 (15 mL), phosgene (20% in toluene, 1.042 mL, 1.97mmol) was added. The mixture was stirred for 15 min, the organic layer was dried over Na2SO4 and concentrated in vacuo, and the residue was treated with a solution of 3-(tert-butyl)-l-(4-methylphenyl)pyrazole-5-ylamine (0.229g) in dichloromethane (10 mL). The resulting mixture was stirred for 17 h at room temperature. After removal of the volatiles in vacuo the residue was purified by flash chromatography using dichloromethane/hexanes/acetone (5:5:1) as elution to give the title compound (0.366g, 57.2%) as a white solid: mp 133-135 0C; 1H NMR (CD3OD/400MHz) delta 7.44 (m, 1H),7.28 (m,lH), 6.97 (m, IH), 6.29 (s, IH), 5.44 (s, 2H), 4.60 (br.lH), 4.45 (s,2H), 2.57 (s, 3H), 2.37 (s, 3H), 1.54 (d, 6H, J = 6.8 Hz), 1.30 (s, 9H); Anal. Calcd for C31H36BrFN6O3: C, 58.22; H, 5.67; N, 13.14. Found: C, 57.72; H, 5.24; N, 12.76. ES-MS m/z 641.39 & 639.39

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/40666; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 285984-25-0, 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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of compounds 10a-d or compounds 17a-d (1.0 mmol) in dichloromethane (10 mL) was slowly added to a stirred solution of triphosgene (109 mg, 0.36 mmol) in dichloromethane (50 mL) over a period of 30 min using a syringe. After stirring for a further 30 min, a solution of compound 25a-r (0.6 mmol) and triethylamine (0.4 mL, 2.77 mmol) in dichloromethane (10 mL) was added in one portion. The reaction mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction was poured into water (50 mL) and extracted three times with dichloromethane. The organic layer was washed with water (5 mL), sat. NaCl solution (5 mL), anddried over Na2SO4. After evaporation of solvent under vacuum, the residue was purified by silica gel chromatography to give the desired chromanylurea or 2H-chromenyl urea compounds.

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, 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Xingzhou; Zhou, Xinming; Zhang, Jing; Wang, Lili; Long, Long; Zheng, Zhibing; Li, Song; Zhong, Wu; Molecules; vol. 19; 2; (2014); p. 2004 – 2028;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-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. COA of Formula: C14H19N3

Intermediate B: Phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate A solution of 3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-amine (Intermediate A) (20 g, 87.0 mmol) in isopropyl acetate (240 mL) was added to a stirred solution of sodium carbonate (11.3 g, 106 mmol) in water (80 mL). After 10 min phenyl chloroformate (12.1 mL, 96 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water (160 mL), the layers were separated and the organics were washed with water (2*80 mL), brine (80 mL), dried (MgSO4) and concentrated in vacuo. The resulting yellow solid was suspended in 10% ether/iso-hexane (320 mL) and stirred until a uniform suspension was obtained. The solid was collected by filtration and washed with iso-hexane to yield the subtitle compound phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate as a white powder (27.3 g, 88%); Rt 2.65 min (Method 1); m/z 350 (M+H)+ (ES+); 1H NMR delta:1.29 (9H, s), 2.37 (3H, s), 6.35 (1H, s), 7.10-7.23 (3H, overlapping m), 7.33-7.46 (6H, overlapping m), 9.99 (1H, s).

The synthetic route of 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LTD; TOPIVERT PHARMA LTD.; LONGSHAW, ALISTAIR IAN; FORDYCE, EUAN ALEXANDER FRASER; ONIONS, STUART THOMAS; KING-UNDERWOOD, JOHN; VENABLE, JENNIFER; US2015/232450; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 285984-25-0, These common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-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.

Preparation 38 5-fert-butyl-2- g-tolyl-2i7-pyrazol-3-ylVcarbamic acid. 2.2.2-trichloro-ethyl ester Add a saturated solution OfNa2CO3 (2.4 L) to a solution of 5-tert-butyl-2-/>-tolyl-2.ff-pyrazol-3- ylamine (400 g, 1.74 mol) in THF (8L) and cool the mixture to 0 C. Then dropwise add 2, 2, 2- trichloroethyl chloroformate (406.77 g, 1.92 mol) and stir the mixture at 0 C for 2 hours. Extract the reaction mixture with ethyl acetate (3 x 6.5L), dry over anhydrous magnesium sulfate and concentrate. Dissolve the solid in a minimal amount of ethyl acetate and add an excess of hexanes to precipitate. Collect the solid by filtration and dry to obtain the title compound as an off white solid (586 g, 83% yield). 1H NMR (400 MHz, CDCl3) delta 7.34 (d, 2H), 7.29 (d, 2H), 6.78 (bs, IH), 6.41 (bs, IH), 4.81 (s, 2H), 2.41 (s, 3H), 1.34 (s, 9H). MS(ES+): m/? = 406.1 [M+H].

The synthetic route of 285984-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/53394; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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.

A saturated aq. solution of NaHCO3 (H mL) was added to a solution of 3-terf-butyl-1 -p-tolyl-1 H- pyrazol-5-amine (WO 2000043384) (206 mg, 0.900 mmol) in DCM (20 mL) and the mixture was cooled to O0C and stirred vigorously whilst trichloromethylchloroformate (325 mul_, 2.70 mmol) was added in a single portion. The vigorous stirring was continued at O0C for a further 80 min. The organic layer was separated and dried and was then evaporated in vacuo to provide 3-te/f-butyl-5-isocyanato-1-p-tolyl-1 /-/-pyrazole, Intermediate B1 as orange oil. This material was pumped for 30 min under high vacuum and was then taken up into THF (6.0 ml.) and kept under nitrogen at O0C and used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Reference:
Patent; RESPIVERT LIMITED; ITO, Kazuhiro; STRONG, Peter; RAPEPORT, William, Garth; MURRAY, Peter, John; KING-UNDERWOOD, John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart, Thomas; JOLY, Kevin; CHARRON, Catherine, Elisabeth; WO2010/67130; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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.

In a 250 mL pre-flask was added 100 mL of ethanol,(30 mmol) of pivaloylacetonitrile,(33. 63 mmol) of 4-methylphenylhydrazine,3. 6 mL of concentrated hydrochloric acid was added dropwise with stirring, heated under reflux for 8 hours,Cooled, concentrated, the residue adjusted with dilute sodium hydroxide PH10-11,Extracted three times with ethyl acetate, dried over anhydrous sodium sulfate, concentrated,The resulting solid was recrystallized from ethyl acetate / petroleum ether to give white crystals C,Yield 80.3%. 5-tert-butyl-2-p-methylphenyl-3-aminopyrazole (3. 5 mmolC) was placed in 100 ml three-necked flask and dissolved in 30 ml of tetrahydrofuran. The three-necked flask was allowed to cool to -20 C, stirring in batches by adding 2. 9g sodium bicarbonate, 15min, dropwise trichloroethyl chloroformate(3. 5 mmol),Control solution temperature does not exceed C,After completion of the dropwise addition, the mixture was stirred for 30 min and then heated to 0 C for 12 h. After completion of the reaction, the mixture was filtered and the residue was rinsed with ethyl acetate and the filtrate was concentrated to yield 85%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Reference:
Patent; institute of pharmacology and toxicology of AMMS; Zhong, Wu; Li, Song; Zhu, Dianxi; LI, Xing-zhou; Zhou, Xin-bo; Wang, Xiaokui; (44 pag.)CN106518767; (2017); A;,
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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., SDS of cas: 285984-25-0

A heterogeneous mixture of a solution of Na2C03 (3.84 g, 36 mmol) in water (42 mL) and Intermediate A (10.5 g, 45.7 mmol) in isopropyl acetate (130 mL, 1 .082 mol) was stirred vigorously at RT for 5 min and was then treated with phenyl carbonochloridate (5.77 mL, 45.7 mmol). Stirring of the mixture was continued for a further 4 hr after which the layers were separated. The organic phase was added to a solution of Intermediate C (10.0 g, 30.5 mmol) and triethylamine (423 mu?, 3.05 mmol) in isopropyl acetate (60 mL, 51 1 mmol). The reaction mixture was warmed to 48 C for 1 hr, then diluted with isopropyl acetate (190 mL) and cooled to RT for a further 18 hr, during which time a precipitate formed. The precipitate was isolated by filtration, washed with isopropyl acetate and then dried in vacuo at 40 C to afford the title compound, Compound (1 ) as a white solid (anhydrous free base, polymorphic form A) (16.5 g, 92 %); R’ 2.74 min (Method 2); m/z 584 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-de) delta: 1.30 (9H, s), 2.41 (3H, s), 6.43 (1 H, s), 6.58 (1 H, d), 6.78 (1 H, t), 6.97 (2H, t), 7.28 (2H, br m), 7.39 (2H, d), 7.40 (1 H, d), 7.49 (2H, d), 7.56 (1 H, m), 7.63 (1 H, m), 7.82 (1 H, dd), 7.95 (1 H, d), 8.10 (1 H, d), 8.40 (1 H, d), 8.77 (1 H, s), 9.16 (1 H, br s), 9.50 (1 H, br s).

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; RESPIVERT LIMITED; ITO, Kazuhiro; CHARRON, Catherine Elisabeth; KING-UNDERWOOD, John; ONIONS, Stuart Thomas; LONGSHAW, Alistair Ian; BROECKX, Rudy; FILLIERS, Walter; COPMANS, Alex; WO2013/50757; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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 2: Synthesis of N-l-(2-(bromomethvnbenzyl>3-(3-tert-butyl-l-P-tolyl-lH- pyrazoI-S-vDnrea.2-(Bromomethyl)benzaldehyde (0.23 g, 1.15 mmol) was dissolved in toluene (30 mL). 3-te/t-Butyl-l-p-tolyl-lH-pyrazol-5-amine (0.158 g, 0.578 mmol), triethylsilane (0.37 mL, 0.269 g, 2.30 mmol), and trifluoroacetic acid (0.222 mL, 0.341 g, 2.99 mmol) were added. The reaction was stirred at 65 0C for five hours. It was allowed to cool to room temperature. Ethyl acetate (50 mL) was added and it was extracted with NaHCO3 (aq.) (50 mL) and H2O (50 mL). The organic phase was dried over MgSO4, filtered, and evaporated. The crude product was purified by flash column chromatography. The resulting solid was recrystallized from ethyl acetate / hexane. (0.140 g, 53 %). IHNMR (400 MHz5 DMSO-J6) delta ppm 1.22 (s, 9H) 2.33 (s, 3H) 4.35 (d, J=5.64 Hz, 2H) 4.74 (s, 2H) 6.25 (s, IH) 6.95 (t, J=5.50 Hz, IH) 7.15-7.35 (m, 7H) 7.34-7.46 (m, IH) 8.21 (s, IH) HRMS (m/z) 455.1444. M+H, C23H27BrN4O requires 455.1441.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/91176; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics