Day: July 21, 2021

These common heterocyclic compound, 398495-65-3, name is 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, 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. Recommanded Product: 398495-65-3

General procedure: To a solution of 2 (13.00 g, 43.90 mmol) and DIEA ( 33.60 g, 260.00 mmol) in dry THF (400 mL) was added dropwise a solution of corresponding acyl chlorides (48.30 mmol) in dry THF (50 mL) over a period of 1 h at room temperature. The reaction mixture was stirred for 12 h at the same temperature and concentrated under reduced pressure. The residue was treated with ethyl acetate / saturated saline (400 mL: 400 mL) and stayed for 2 h, and then filtered. The precipitate was washed with diethyl ether (30 mL), and dried in vacuo to yield the title compounds 3a-d. 3e was obtained by flash chromatography (180 g silica gel, petroleum ether/AcOEt, 0-30%, V/V).

The synthetic route of 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Xiao-Guang; Yu, Dong-Ke; Wang, Ju-Xian; Zhang, Hao; He, Hong-Wei; Shao, Rong-Guang; Wang, Yu-Cheng; Li, Xue-Mei; Bioorganic and medicinal chemistry letters; vol. 22; 22; (2012); p. 6947 – 6951,5;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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 4149-06-8, Recommanded Product: 4149-06-8

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 41680-34-6, name is 3-Amino-1H-pyrazole-4-carboxylic acid, 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. Recommanded Product: 41680-34-6

To a stirred solution of 5-amino-1H-pyrazole-4-carboxylic acid (10.0 g, 71.4 mmol) in ethanol (100 mL), was added sodium ethoxide (17.0 g, 245 mmol) followed by 1,3-dimethyluracil (11.0 g, 78.6 mmol). The reaction mixture was then stirred at reflux overnight under an argon atmosphere. The mixture was poured into ice-water, and the resultant solution was acidified to about pH 3-4 with concentrated HCl. The suspension was stirred for 2 hours and then filtered to afford the intermediate, which was used without further purification (10.0 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): 8.54 (d, J=9.2 Hz, 1H), 8.06 (s, 1H), 6.11 (d, J=7.2 Hz, 1H).

The synthetic route of 3-Amino-1H-pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; US2012/22043; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 5775-86-0, The chemical industry reduces the impact on the environment during synthesis 5775-86-0, name is 4-Bromo-1,5-dimethylpyrazole, I believe this compound will play a more active role in future production and life.

To compound 264.4(5.Og, l6mmol, 1.Oeq) and 4- bromo-1,5-dimethyl-1H-pyrazole (2.74g, l4mmol, 0.84eq) in 1,4-dioxane (4OmL), potassium carbonate (6.96g, 48mmol, 3.Oeq) was added. Argon gas was purged through the reaction for 10- 1 5mm. Then, [1,1 ?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)] complex with CH2C12 (0.41g, 0.48mmol, 0.O3eq) was added. Reaction mixture was stirred at 100-110 C for 3h. After completion of the reaction, the reaction mixture was transferred to water and extracted with ethyl acetate. Organic layers were combined, dried over anhydrous Na2SO4, filtered and evaporated under vacuum to obtain 264.5 (1.5g, 33.6%). MS(ES): m/z 266.37 [M+H]t

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, 4-Bromo-1,5-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3524-32-1, 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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 C) 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 (3×50 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 (3×30 ml) and identified by TLC and 1H NMR.

The synthetic route of 5-Amino-1,3-dimethylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lyalin, Boris V.; Sigacheva, Vera L.; Kokorekin, Vladimir A.; Petrosyan, Vladimir A.; Mendeleev Communications; vol. 25; 6; (2015); p. 479 – 481;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, 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. COA of Formula: C5H6N2O2

1) N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide N,O-dimethylhydroxylamine hydrochloride (1.30 g) was added to an N,N-dimethylformamide (32 mL) solution that contained 1-methyl-1H-pyrazol-5-carboxylic acid (1.21 g), O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (4.38 g) and diisopropylethylamine (3.34 mL) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, chloroform_methanol=100:0 to 95:5), so as to obtain the title compound (1.03 g) in the form of a yellow oily substance. 1H NMR (200 MHz, CHLOROFORM-d) delta ppm 3.36 (s, 3H) 3.66 (s, 3H) 4.13 (s, 3H) 6.77 (d, J=2.20 Hz, 1H) 7.48 (d, J=2.20 Hz, 1H); MS (ESI pos.) m/z: 170 [M+H]+

The synthetic route of 16034-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Nakamura, Toshio; Sakagami, Kazunari; Konishi, Kazuhide; Yamamoto, Kanako; Masuda, Seiji; Matsuda, Yohei; Okada, Kumiko; Shibata, Tsuyoshi; Ohta, Hiroshi; Yasuhara, Akito; Kawamoto, Hiroshi; Amada, Hideaki; Urabe, Hiroki; Nishikawa, Rie; Kashiwa ASHIWA, Shuhei; US2013/137865; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 706819-66-1, name is 2-Bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone, 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. Safety of 2-Bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone

2-Bromo-1 -(1 -methyl-1 H-pyrazol-4-yl)-ethanone (CAS 706819-66-1) (820 mg; 4.04 mmol) was added to a mixture of intermediate 2 (1 g; 3.36 mmol) and K2C03 (930 mg; 6.73 mmol) in DMF (20 mL). The reaction mixture was heated at 65C for 18 hours. The reaction mixture was cooled to room temperature, poured onto water and extracted with EtOAc. The organic layer was decanted, washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH 40g; mobile phase: 95% DCM, 5% MeOH, 0.5% NH4OH). The pure fractions were collected and evaporated to dryness, yielding 345 mg (25%) of intermediate 3. 1H NMR (500 MHz, DMSO-d6) delta 9.78 (s, 1 H), 9.27 (s, 1 H), 9.09 (s, 1 H), 8.71 (s, 1 H), 8.31 (s, H), 7.01 (t, J = 7.88 Hz, 1 H), 3.79 – 4.05 (m, 9H); MS (ESI+) m/z (%) (r.t. 2.34) 400 (100) [M+H]+, 799 (95) [2M+H]+ (method B1 ). MP. : 224C (Kofler).

The synthetic route of 2-Bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; SAXTY, Gordon; HAMLETT, Christopher Charles Frederick; BERDINI, Valerio; MURRAY, Christoper William; ANGIBAUD, Patrick Rene; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; WO2013/179033; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 96799-02-9, A common heterocyclic compound, 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, molecular formula is C7H7N3O, 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.

6- amino-benzothiazole (188 mg, 1.25 mmol) and DIPEA (0. 22 mL, 1.25 mmol) were added to a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) at 0 0C. The reaction mixture was stirred at 0 0C to room temperature for 2 hours. 3-amino-5-(2- furyl) pyrazole (187 mg, 1.25 mmol) and DIPEA (0.22 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 0C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column and eluted with 0- 5 % MeOH/DCM which afforded compound 37 as a white solid (200 mg, 34%). 1H NMR (400 MHz, DMSO-d6) delta 12.86 (bs, IH, NH), 10.99 (bs, IH, NH), 9.61 (bs, IH, NH), 9.21 – 6.59 (m, 8H, Ar-H), 4.68 (bs, 2H, CH2), 3.43 (bs, 2H, CH2), 3.09 (bs, 4H, 2CH2), 2.76 (s, 3H, CH3); ESI-MS: calculated for (C22H22Ni0OS) 474, found 475 [M+H]+. HPLC: retention time: 14.52 min. purity: 97%.

The synthetic route of 96799-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; HO, David; DESAI, Neil, P.; WO2010/144550; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 162758-35-2,Some common heterocyclic compound, 162758-35-2, name is 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, molecular formula is C17H11Cl3N2O2, 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 the carboxylic acid (1 eq) in dry dichloromethane, was added N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDC.HCl, 1.2 eq), Hydroxybenzotriazole (1.2 eq) and diisopropylethyl amine (3 eq) at 0C. Then the amine (1.1 eq) was added and stirred at RT for 6h. To the reaction mixture, water was added and the organic layer was separated, washed with saturated NaHCO3, 1N HCl, dried over Na2SO4 and concentrated under reduced pressure. This crude mixture was purified by column chromatography to give the pure compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, its application will become more common.

Reference:
Article; Ramesh, Remya; Shingare, Rahul D.; Kumar, Vinod; Anand, Amitesh; B, Swetha; Veeraraghavan, Sridhar; Viswanadha, Srikant; Ummanni, Ramesh; Gokhale, Rajesh; Srinivasa Reddy; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 723 – 730;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 139756-02-8, A common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, molecular formula is C8H14N4O, 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.

General procedure: We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1).

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:
Article; Reddy, G. Lakshma; Guru, Santosh Kumar; Srinivas; Pathania, Anup Singh; Mahajan, Priya; Nargotra, Amit; Bhushan, Shashi; Vishwakarma, Ram A.; Sawant, Sanghapal D.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 201 – 208;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics