Category: 35100-92-6

Electric Literature of 35100-92-6,Some common heterocyclic compound, 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, molecular formula is C5H9N3, 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: To a solution of benzoic acid which was obtained by hydrolysis of methyl esters 8 or 12A-E (0.22 mmol, 1.0 equiv), aminothiazole or imidazo[1,2-a]pyrazin-8-amine or aminopyrazole (0.33 mmol, 1.5 equiv), HATU (0.33 mmol, 1.5 equiv) and HOAt (0.33 mmol, 1.5 equiv) in DMF (2 mL) was added dropwise di(isopropyl)ethylamine (DIPEA) (0.12 mL, 0.67 mmol, 3 equiv). The reaction was run under microwave at 60 C (40 W) for 30 min, and then cooled to room temperature and poured into brine. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous NaSO4 and concentrated. The residue was purified by chromatography (SiO2, petroleum ether/EtOAc = 4:1-1:1) to yield corresponding amides as white or yellow powder.

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

Reference:
Article; Mao, Weiwei; Ning, Mengmeng; Liu, Zhiqing; Zhu, Qingzhang; Leng, Ying; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2982 – 2991;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35100-92-6, A common heterocyclic compound, 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, molecular formula is C5H9N3, 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 2.01 2- [ [2- [(1 ,5-Dimethylpyrazol-3-yl)aminol -5-(trifluoromethyl)-4-pyridyll aminol -N- methyl-benzamide l,5-Dimethylpyrazol-3-amine (50.6 mg, 0.45 mmol), 2-[[2-chloro-5- (trifluoromethyl)pyridin-4-yl] amino] -N-methylbenzamide (100 mg, 0.30 mmol), sodium te/t-butoxide (43.7 mg, 0.45 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (35.1 mg, 0.06 mmol) and bis(dibenzylideneacetone)palladium (27.8 mg, 0.048 mmol) were suspended in dioxane (3 mL) and the mixture heated at 1500C for 30 minutes in a microwave reactor. The mixture was allowed to cool to room temperature and then loaded onto an SCX column. The mixture was eluted first with MeOH and then with a solution of 7N NH3 in MeOH. Fractions containing product were combined and then evaporated. The residue was purified by preparative HPLC and fractions containing product were combined and evaporated to leave example 2.01 (28.4 mg, 23% yield); 1H NMR spectrum: (300 MHz, DMSO) delta 2.18 (3H, s), 2.77 (3H, d), 3.55 (3H, s), 5.93 (IH, s), 7.08 – 7.11 (IH, m), 7.52 – 7.55 (IH, m), 7.61 – 7.63 (2H, m), 7.69 – 7.72 (IH, m), 8.21 (IH, d), 8.64 (IH, q), 9.36 (IH, s), 10.25 (IH, s); Mass spectrum: m/z (ESI+) (M+H)+ = 405.07.

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; ASTRAZENECA UK LIMITED; WO2009/153589; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35100-92-6, 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 35100-92-6 as follows.

6- (4 – ((2,5-dichloro-4-yl) amino) piperidin-1-yl) -3-cyano-pyridine (100mg, 0.286mmol) in n-butanol (5mL) solution of was added 1,5-dimethyl -1H- pyrazol-3-amine (40mg, 0.41mmol) and trifluoroacetic acid (212muL, 2.86mmol). The resultant reaction system was heated up to 120 deg.] C, sealed tube for 24 hours, until the reaction system was cooled to room temperature, concentrated under reduced pressure. To the resulting residue was added ethyl acetate (50 mL) was diluted and washed with water (15mL × 3) washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography Analysis (DCM / EtOAc / MeOH (v / v / v) = 25/5/1) to give the title compound as a whiteSolid (53mg, 44% yield)

According to the analysis of related databases, 35100-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (105 pag.)CN105461694; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 35100-92-6,Some common heterocyclic compound, 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, molecular formula is C5H9N3, 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 9 Preparation of N-(1,5-dimethylpyrazol-3-yl)-2,6 dimethyl benzamide (compound 3) To a cooled (0-5 C.) solution of 3-amino-1,5-dimethyl pyrazole (95%, 32.7 g, 0.28M) in anhydrous CH2 Cl2 (200 ml) was added a CH2 Cl2 (100 ml) solution of the 2,6 dimethyl benzoyl chloride (23.6 g, 0.14M). The reaction mixture was allowed to room temperature for 18 hours and then CH2 Cl2 was concentrated to give an oily mixture which was diluted in AcOEt. This suspension was then treated with saturated NaHCO3. After usual work-up, the crude material was cristallized with diisopropyloxide to give 13 g of the desired amide (38%: yield based on the 2,6-dimethyl benzoyl chloride). m.p.: 184 C.

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

Reference:
Patent; Novapharme; US5464860; (1995); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-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 35100-92-6, category: pyrazoles-derivatives

To an orange, homogeneous solution of methyl 2-oxo-2H-pyran-3-carboxylate (1.9201 g, 12.46 mmol) in DMF (12.44 ml) under nitrogen at 0 C was added 1,5- dimethyl-1H-pyrazol-3-amine (1.3 822 g, 12.44 mmol).. After 6 h, the cold bath wasremoved, and the reaction was stirred to room temperature for 15 mm EDCI (1-(3-dimethylaminopropyl) ethyl carbodiimide) (3.10 g, 16.17 mmol) and DMAP (0.380 g,3.11 mmol) were added. After stirring overnight, the reaction was diluted with EtOAc(200 mL) and water (50 mL). The layers were separated, and the organic layer waswashed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered andconcentrated in vacuo to give a residue which was purified by flash chromatographyusing an ISCO 330g column (solid loading) eluting with 10-100% EtOAc/hex. Appropriate fractions were collected and concentrated in vacuo to give methyl 1-(1,5- dimethyl- 1 H-pyrazol-3 -yl)-2-oxo- 1 ,2-dihydropyridine-3 -carboxylate (0.8397 g, 3.40 mmol, 27.3 % yield) as a light orange solid.

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; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); 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. 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

Example 65 Synthesis of N-(1,5-Dimethyl-1H-pyrazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine (Cpd. No. 115) Pd2(dba)3 (27 mg, 0.03 mmol) and BINAP (37 mg, 0.06 mmol) were mixed in anhydrous toluene (5 mL). The mixture was heated at reflux for 3-4 minutes. This clear, orange-red color solution was transferred into a round-bottom flask containing S13 (102 mg, 0.3 mmol), 1,5-dimethyl-1H-pyrazol-3-amine (70 mg, 0.6 mmol), K3PO4 (212 mg, 1.0 mmol), and anhydrous toluene (5 mL). The mixture was heated at reflux for overnight before quenching with methanol. The reaction mixture was filtered through a pad of Celite and the organic layer was collected, concentrated, and purified by HPLC to yield Cpd. No. 115 in 31 mg as a CF3CO2H salt. 1H NMR (300 MHz, MeOD-d4): 8.24 (s, 1H), 7.46 (s, 1H), 6.25 (s, 1H), 3.98 (s, 3H), 3.90 (s, 3H), 2.84 (s, 3H), 2.39 (s, 3H), 2.33 (s, 3H), 2.16 (s, 3H). ESI-MS calculated for C22H24N7O2 [M+H]+=418.20, Observed: 418.50.

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 35100-92-6.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35100-92-6, 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. 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 2 6-(4-(5-chloro-2-(1,5-dimethyl-1H-pyrazol-3-yl)amino)pyrimidin-4-ylamino)piperidin-1-yl)nicotinonitrile To a solution of 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-1-yl)nicotinonitrile (100 mg, 0.286 mmol) in n-butanol (5 mL) was added 1,5-dimethyl-1H-pyrazol-3-amine (95 mg, 0.859 mmol) and TFA (212 muL, 2.86 mmol). The reaction mixture was stirred at 120 C. in a sealed tube for 24 hours then cooled to room temperature and diluted with EtOAc (50 mL), washed with water (15 mL*3) followed by brine (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/EA/MeOH (v/v/v)=25/5/1) to give the title compound as a white solid (53 mg, yield 44%). LC-MS (ESI, pos. ion) m/z: 423.7 [M+H]+; 1H NMR (300 MHz, DMSO-d6) delta (ppm): 9.17 (s, 1H), 8.49 (d, J=2.3 Hz, 1H), 7.87 (s, 1H), 7.84 (dd, J=9.1, 2.3 Hz, 1H), 7.00 (d, J=9.2 Hz, 1H), 6.78 (d, J=7.8 Hz, 1H), 6.35 (s, 1H), 4.57-4.51 (m, 2H), 4.32-4.19 (m, 1H), 3.60 (s, 3H), 3.07-2.99 (m, 2H), 2.22 (s, 3H), 2.00-1.95 (m, 2H), 1.65-1.52 (m, 2H).

The synthetic route of 1,5-Dimethyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (78 pag.)US2016/229837; (2016); A1;,
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. 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 1,5-Dimethyl-1H-pyrazol-3-amine

To a solution of 3-amino-1,5-dimethylpyrazole (0.50 g) and triethylamine (0.63 ml) in chloroform (5 ml), 2-fluoro-3-(trifluoromethyl)benzoyl chloride (0.65 ml) was added under ice cooling. The reaction solution was stirred at room temperature for 0.5 hours, washed with an aqueous 2M sodium hydroxide solution, dried over anhydrous sodium sulfate and filtrated. Thereafter, the filtrate was concentrated under vacuum. The residue obtained was washed with n-hexane to obtain a colorless solid substance of N-(1,5-dimethylpyrazol-3-yl)-2-fluoro-3-(trifluoromethyl)benzamide (1.25 g). 1H-NMR(200 MHz, CHLOROFORM-D) d ppm; 2.30 (s, 39H), 3.72 (s, 3H), 6.59 (s, 1H), 7.40 (t, J =7.5 Hz, 1H), 7.78 (t, J = 7.5 Hz, 1H), 8.34 (td, J = 7.5 Hz, 1H), 8.60-8.89. (br. s, 1H) MS (ESI)(Positive)m/z; 302 (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.

Adding a certain compound to certain chemical reactions, such as: 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-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 35100-92-6, category: pyrazoles-derivatives

73 Preparartion of N.N-dicvclopropyl-6-ethyl-l-methyl-4-(l ,5-dimethyl-lH- pyrazol-3-ylamino)-1.6-dihydroimidazo[4.5-dlpyrrolo[2.3-blpyridine-7-carboxamide[00362] To a vial containing 1,5 -dimethyl- lH-pyrazol-3 -amine (13.60 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 muiotaetaomicron), Xantphos (5.90 mg, 10.20 muiotaetaomicron), and cesium carbonate (100 mg, 0.306 mmol) was added N,N-dicyclopropyl-6-ethyl-4-iodo- 1- methyl-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (45.8 mg, 0.102 mmol) in DME (1020 muKappa). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 90 C 1 h. The reaction mixture was diluted with dichloromethane and vacuum filtered through Celite. The filtrate was concentrated in vacuo. The crude residue was purified via flash column chromatography using an ISCO 12 g column eluting with 1 – 10%MeOH/CH2Cl2). N,N-Dicyclopropyl-4-(l,5-dimethyl-lH-pyrazol-3-ylamino)-6- ethyl- l-methyl-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (14 mg, 31.7 % yield) was isolated as an off-white solid.[00363] MS (ESI) m/z 433.2 (M+H).[00364] XH NMR (500 MHz, CDC13) delta: 8.19 (s, 1H), 7.63 (s, 1H), 6.94 (s, 1H), 6.85 (s, 1H), 4.65 (q, J = 7.0 Hz, 2H), 3.99 (s, 3H), 3.71 (s, 3H), 2.79 – 2.85 (m, 2H), 2.33 (s, 3H), 1.49 (t, J = 7.2 Hz, 3H), 0.82 – 0.87 (m, 4H), 0.72 – 0.78 (m, 4H)

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.

Application of 35100-92-6, 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. 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows.

Combine c/s-4-[(4-bromo- I -methyi-1H-benzimidazoi-6-vi)oxyj cyciohexanamine(25.70 g, 79.27 rnrnol), 1.5-dimethyi-1H-pyrazol-3-arnine (9.08 g, 1.0 eq), potassiumcarbonate (28.48 g, 2.6 eq), 2-(dicyclohexvlphosphino)3,6-dimethoxy-2?,4?,6?- tisopropyi- 1,1 ?-biphenyl (8.60 g, 0,20 eq), tris(dibenzylideneacetone)dipailadium(0) (3.63 g, 0.050 eq), and acetic acid (0.14 rnL) in tert-butyl alcohol (250 mL). Heat at reflux overnight. Concentrate the reaction mixture in vacuo. Add DCM and water;separate the layers. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo. Triturate from EtOAc and hexanes to give a tan solid. Subject the tan solid to normal phase chromatography, eluting with hexanes, then 5% MeOFI in DCM, then 20% 2M amrnoniated MeOH in DCM, to give the title compound as a tan solid (21,71 g, 77%). MS (ES) m/z = 355 (M-t-H).

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