Category: 3528-45-8

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. 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Product Details of 3528-45-8

To an ice-cooled solution of 2-(4-methoxy-benzyl)-2eta-pyrazol-3-ylamine (406 mg, 2.0 mmol, 1.0 eq.) in DCM (5 mL), DIPEA (0.52 ml, 3.0 mmol, 1.5 eq.) was added.A solution of bromoacetyl bromide (0.19 ml, 2.2 mmol, 1.1 eq.) in DCM (2 mL) was added dropwise. The cooling bath was removed and the brown solution was stirred at r.t. for 1.5 hours. The solution was diluted with AcOEt (75 mL), washed with sat. aq.NaHCO3 soln. (1 x 40 mL), with sat. aq. NaCl soln. (1 x 40 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by CC (SiO2, AcOEt/Hept 1 :1 to6:4) to give the desired bromide as a beige solid.LC-MS (A): tR = 2.60 min; [M-H]+ = 322.3.

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; ACTELION PHARMACEUTICALS LTD; WO2009/150614; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3528-45-8, 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. 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A stirred mixture of triethoxymethane (339 mL, 2037 mmol), and 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum’s acid) (35.2 g, 244 mmol) was heated to 80 C. for 1 hour. A suspension of 1-(4-methoxybenzyl)-1H-pyrazol-5-amine [41.4 g, 204 mmol; prepared according to the procedure described by Misra, R. N., et al. Bioorg. Med. Chem. Lett. 2003, 13, 1133-1136, except desalting was performed as follows: 1-(4-methoxybenzyl)-1H-pyrazol-5-amine hydrochloride (44 g) was partitioned between MTBE (300 mL) and 1N aqueous NaOH (300 mL), after separating the phases, the aqueous suspension was re-extracted with MTBE (8×100 mL), followed by drying (Na2SO4) the combined organic phases, and concentration in vacuo to obtain the free-based 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (30 g)] in triethoxymethane (339 mL, 2037 mmol) was added at once and heating at 80 C. was continued for 18 hours under N2. After cooling to room temperature, toluene azeotrope (2×200 mL) was utilized to remove EtOH. The resulting suspension was diluted with diethyl ether (500 mL) and filtered to obtain a yellow solid (33.5 g, 46%). 1H NMR (400 MHz, CDCl3) delta 11.13 (d, J=13 Hz, 1H), 8.26 (d, J=13 Hz, 1H), 7.50 (d, J=2 Hz, 1H), 7.25 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 6.21 (d, J=2 Hz, 1H), 5.28 (s, 2H), 3.78 (s, 3H), 1.74 (s, 6H).

The synthetic route of 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blake, James F.; Boyd, Steven Armen; De Meese, Jason; Fong, Kin Chiu; Gaudino, John J.; Kaplan, Tomas; Marlow, Allison L.; Seo, Jeongbeob; Thomas, Allen A.; Tian, Hongqi; Cohen, Frederick; Young, Wendy B.; US2007/238726; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3528-45-8,Some common heterocyclic compound, 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine, molecular formula is C11H13N3O, 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-(4-Methoxybenzyl)-1H-pyrazol-5-amine (3.94 g, 1 9.39 mmol), followed by diethyl 2-(ethoxymethylene)malonate (4 mL, 20 mmol) was added to a 200 mL round bottom flask fitted with a distillation head to remove ethanol. The mixture was heated to 130 C for 45 min, then 10 mL of diphenyl ether was added and the temperature was raised to 240 C for 2 h. The reaction mixture was then cooled to rt and Et2O ( 1 00 mL) was added. The resulting precipitate was collected by vacuum filtration and dried under vacuum to afford the target compound as a white solid (4 g, 62%).

The synthetic route of 3528-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH,INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Kanl H.; DRAGOVICH, Peter; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; YUEN, Po-Wai; ZAK, Mark; ZHANG, Yamin; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/127268; (2013); A1;,
Pyrazole – Wikipedia,
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. 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine

In a stirred solution of 1a (15.0 g, 74 mmol) and diethyl acetylmalonate (15.0 g, 74 mmol), in POCI3 (110 mL) at O0C, a stream of dry HCI gas is passed over the solution for a period of about 15 min. The reaction mixture is gradually warmed to RT, stirred for about 2 h and then heated to 60 0C for about 4 h. POCI3 is distilled under reduced pressure. The reaction mixture is quenched with ice and extracted with EtOAc (3 x 75 mL). The combined organic layers are washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The pure intermediate 1b (9.0 g, 31.5% yield) is isolated as a yellow oil by flash chromatography with Petroleum ethenEtOAc (85:15 v/v).

The synthetic route of 3528-45-8 has been constantly updated, and we look forward to future research findings.

Related Products of 3528-45-8, A common heterocyclic compound, 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine, molecular formula is C11H13N3O, 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 solution of 3-[l-(2,3-dimethyl-phenyl)-lH-tetrazol-5-yl]-propionic acid (49 mg, 0.20 mmol, 1.0 eq.) and 2-(4-methoxy-benzyl)-2H-pyrazol-3-ylamine (40 mg, 0.20 mmol, 1.0 eq.) in DMF (1.2 mL), lambda/-(3-dimethylaminopropyl)-lambdaf-ethylcarbodiimide hydrochloride (57 mg, 0.30 mmol, 1.5 eq.) and 4-dimethylaminopyridine (36 mg, 0.30 mmol, 1.5 eq.) were added in sequence. The mixture was stirred at r.t. for 18 hours. The mixture was purified by prep. etaPLC and evaporated to afford the title compound. LC-MS (B): tR = 0.85 min; [M+eta]+ = 432.12.

The synthetic route of 3528-45-8 has been constantly updated, and we look forward to future research findings.

Reference of 3528-45-8, These common heterocyclic compound, 3528-45-8, name is 1-(4-Methoxybenzyl)-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 4: Synthesis of 3-(4-methoxybenzyl)-9-(methylsulfanyl)-6,7-dihydro-3H- pyrazolo[4′,3′:5,6]pyrido[4,3-f]quinazoline. To a mixture of (E)-6- ((dimethylamino)methylene)-2-(methylthio)-7,8-dihydroquinazolin-5(6H)-one (8 g, 32 mmol) and l-(4-methoxybenzyl)-lH-pyrazol-5 -amine (7.2 g, 35 mmol) was added trifluoroacetic acid (3 mL). The reaction mixture was heated at 100 0C for 16 hours. The reaction was cooled to room temperature and diluted with a 1 : 1 mixture of methanol and isopropanol (40 mL). The mixture was stirred for 30 minutes and filtered. The solid obtained was then further purified using flash column chromatography (SiO2, gradient from 100% chloroform to 2% EtOAc in chloroform) to give the desired product (3.0 g, 24%) as a yellow solid. 1H NMR (CDCl3, 400MHz): delta 9.52 (s, IH), 7.98 (s, IH), 7.82 (s, IH), 7.40 (d, J = 8.0 Hz, 2H), 6.82 (d, J = 8.0 Hz, 2H), 5.64 (s, 2H), 3.78 (s, 3H), 3.16 (t, J = 6.0 Hz, 2H), 3.10 (t, J = 6.2 Hz, 2H), 2.65 (s, 3H); LCMS [M+H]: 390.

The synthetic route of 3528-45-8 has been constantly updated, and we look forward to future research findings.

Related Products of 3528-45-8,Some common heterocyclic compound, 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine, molecular formula is C11H13N3O, 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 an ice-cooled solution of 2-(4-methoxy-benzyl)-2H-pyrazol-3-ylamine (406 mg, 2.0 mmol, 1.0 eq.) in DCM (5 mL), DIPEA (0.52 ml, 3.0 mmol, 1.5 eq.) was added. A solution of bromoacetyl bromide (0.19 ml, 2.2 mmol, 1.1 eq.) in DCM (2 mL) was added dropwise. The cooling bath was removed and the brown solution was stirred at r.t. for 1.5 hours. The solution was diluted with AcOEt (75 mL), washed with sat. aq. NaHCO3 soln. (1¡Á40 mL), with sat. aq. NaCl soln. (1¡Á40 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by CC (SiO2, AcOEt/Hept 1:1 to 6:4) to give the desired bromide as a beige solid.LC-MS (A): tR=2.60 min; [M-H]+=322.3.

The synthetic route of 3528-45-8 has been constantly updated, and we look forward to future research findings.

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. 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Product Details of 3528-45-8

A mixture of 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (3 g, 10 mmol) and (ethoxymethylene)propanedioic acid, diethyl ester (3.8 g, 18 mmol) was heated at 120 C. for 1.5 h, then allowed to cool. After cooling, the mixture was concentrated and the resulting residue was purified with CombiFlash eluting with 0-30% EtOAc in hexanes to give an intermediate, LCMS (M+H): 374.1. The intermediate was dissolved in diphenyl ether (5 mL). The resulted solution was heated at 240 C. in microwave reactor for 1 h 20 min. After cooling, the solid crashed out was filtered and washed with hexanes to afford 4.0 g (80%) of the sub-title compound. LCMS calc. for C17H18N3O4 (M+H)+: m/z=328.1. Found: 328.1

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.