Category: pyrazoles-derivatives

Some common heterocyclic compound, 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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. category: pyrazoles-derivatives

Into a 25 mL round-bottom flask, were placed intermediate 44.3 (300 mg, 0.74 mmol, 1.00 equiv), 1-methyl-1H-pyrazol-4-amine hydrochloride (119 mg, 0.89 mmol, 1.20 equiv), hydrogen chloride in dioxane (0.5 mL) and n-BuOH (5 mL). The reaction was stirred for 12 h at 110 C. Upon completion of the reaction resulting mixture was concentrated under vacuum. The solution was adjusted to pH 9-10 with sodium hydroxide (2M) and resulting solids were collected by filtration. The crude product was purified by recrystallization from methanol to furnish 208.8 mg (61%) of compound 1-45 as a yellow solid. LCMS (ES, mlz): 465.4[M+H] ?H NMR (300MHz, CD3OD): 7.86 (1H, s), 7.54 (1H, s), 6.75-7.11 (1H, t), 4.05 (1H, s), 3.85 (3H, s), 3.78 (4H, t), 2.60 (4H, s), 2.08-2.32 (5H, m), 1.29-1.47 (4H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127107-23-7, its application will become more common.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
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Some common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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. HPLC of Formula: C4H5N3O2

General procedure: Compound 30-3 and 3-bromo-2-(bromomethyl)prop-l -ene are combined with K -CO . in DMF to give compound 47-1. Compound 47-1 is combined with lithium bis(trimethylsilyl)amide to give compound 47-2, Compound 47-2 is combined with NaB in MeOH to give compound 47-3, Compound 47-3 is combined with compound 1-1, PPh3, and DIAD in THF to give compound 47-4. To compound 47- 4 in MeOH is added Pd/C, and the mixture is stirred under H2 to produce compound 47-5. Compound 47- 5, compound 5-5, and TsOH are combined in 1 ,4-dioxane to give compound D-52

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5334-39-4, its application will become more common.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
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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. 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7N3O

Example 15To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added benzylmercaptan (0.19 mL, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino-5-(2- furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.36 mL, 3.26 mmol) and DIPEA (0.57 mL, 3.26 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C 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 eluted with 0-5 % MeOH/DCM afforded 15 as white solid (250 mg, 34 %). 1H NMR (400 MHz, DMSOd6) delta 12.83 (s, 1H, NH), 9.92 (bs, 1Eta, NH), 7.74-6.59 (m, 9Eta, Ar-H), 4.34 (s, 2Eta, CH2), 3.75 (s, 4Eta, 2CH2), 2.34 (s, 4Eta, 2CH2), 2.29 (s, 3Eta, CH3); ESI-MS: calcd for (C22Eta24N8OS) 448, found 449 [M+H]+. HPLC: retention time: 20.34 min. purity: 99%.

According to the analysis of related databases, 96799-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; HO, David; NALLAN, Laxman; POLAT, Tulay; SUN, Xiaowen; DESAI, Neil; WO2010/144394; (2010); A1;,
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These common heterocyclic compound, 15878-00-9, name is 4-Chloro-1H-pyrazole, 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: 4-Chloro-1H-pyrazole

EXAMPLE 5 7.65 g (0.075 mole) of 4-chloropyrazole were suspended in 100 ml of water and the suspension obtained first had added to it 72 g (0.64 mole) of a 50% strength aqueous KOH solution and then at 0 C. 17 g (0.15 mole) of a 30% strength aqueous hydrogen peroxide solution. After the reaction mixture had been stirred for 5 minutes, 28 g (0.18 mole) of phthalic anhydride were added in small portions at 10 C., and the whole was stirred overnight and then worked up similarly to Example 1. Yield: 7.1 g of 4-chloro-N-hydroxypyrazole, corresponding to 80% of theory.

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

Reference:
Patent; Basf Aktiengesellschaft; US4945167; (1990); A;,
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. 17635-44-8, name is 3,4,5-Tribromopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 17635-44-8

General procedure: 3,4,5-Tribromopyrazole (9a; 762 mg, 2.5 mmol) or 3,5-dibromo-4-nitropyrazole(9b; 677 mg, 2.5 mmol), o-quinone methide precursor 2(2.5 mmol) and K2CO3 (only for 9a, 1.035 g, 7.5 mmol) were refluxedfor 4 h in DMF (10 mL). Product was isolated analogously to compound4a.

The synthetic route of 17635-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
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Electric Literature of 89717-64-6, 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. 89717-64-6, name is 4-Bromo-3-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-3- nitro-lH-pyrazole (1.5 g, 7.8 mmol) in anhydrous THF (50 mL) was added phenylboronic acid (0.95 g, 7.8 mmol), copper(II) acetate (2.1 g, 11.7 mmol) and pyridine (2.5 g, 31.2 mmol. The mixture was stirred overnight at 40C under oxygen atmosphere. After removing the insolubles by filtration, the filtrate was diluted with EtOAc (50 mL), washed with water (50 mL) and brine (50 mL), dried over a2S04, filtered and concentrated in vacuo to obtain a residue which was purified by silica gel chromatography (eluting with hexane/EtOAc = 1/1) to afford 4-bromo-3-nitro-l -phenyl- lH-pyrazole as a yellow solid (2.0 g, Yield: 95%). ESI- LCMS (m/z): 268.0 [M+l]

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

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; (178 pag.)WO2016/44666; (2016); A1;,
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Synthetic Route of 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.

in two screw-top glass pressure vessels, split and combine the following amounts in two equal portions 2-(2-chioro-4-pyridyi)-5-(2-nethoxyethyi)-6,6-dimethyi-thieno[2,3- c]pyrroi-4-one (13 g, 38.59 mmol), 1-methyi-5-aminopyrazole (11.245 g, 115.78 mmoi),cesium carbonate (37.724 g, 115.78 mrnol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (2.010 g, 3.47 mmoi), paiiadium(ii)acetate (520 mg, 2.32 nmoi) and 1,4-dioxane (350 mL). Seal each vessel and heat at 110 °C overnight.Dilute the reaction mixture with 10percent MeOH in DCM (2 L) and wash the resulting solution with saturated NaC1. Back extract the aqueous solution with DCM and combinethe organic solutions. Dry the combined solutions over a mixture of an hyous sodium sulfate and aithydrous magnesium sulfate, filter and concentrate the filtrate under reduced pressure. Purify by silica gel chromatography by loading the residue onto a 260 g loading coiunm with DCM and then eluting the loading coiunm onto a 750 g silica gel column with a gradient of 60-100percent of 10percent MeOH in EtOAc in hexane to yield the titlecompound 8.4 g (55percent). MS rn/z): 398 (M+i).

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; ELI LILLY AND COMPANY; CORTEZ, Guillermo S.; JOSEPH, Sajan; MCLEAN, Jonathan Alexander; MCMILLEN, William T.; RODRIGUEZ, Michael John; ZHAO, Gaiying; (70 pag.)WO2016/106009; (2016); A1;,
Pyrazole – Wikipedia,
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Synthetic Route of 5744-40-1, The chemical industry reduces the impact on the environment during synthesis 5744-40-1, name is Ethyl 1,3-dimethyl-1H-pyrazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

d. Alternative synthesis of 1.S-dimethylpyrazole-delta-carboxylic acid; Ethyl-2,4-dioxovalerate (Kg) is added to a solution of methyl hydrazine (L) in ethanol (L) and heated to 6O0C for 18 hours to provide the intermediate 3,5-dimethyl-pyrazole-5- carboxylic acid ethylester.

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, Ethyl 1,3-dimethyl-1H-pyrazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2006/48761; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 5071-61-4 as follows. SDS of cas: 5071-61-4

A solution of acid 4 (0.09 g, 0.47 mmol) in dry DMF (2 mL) treated sequentially with amine (5a-i, 6a-e and 7a-h; 0.517 mmol)and triethylamine (0.94 mmol) was stirred under a N2 atmosphere for 15 min, later TBTU (0.56 mmol) was added and reaction mixture refluxed for 4-10 h. The reaction mixture was quenched with aq satd NH4Cl solution (10 mL). After 10 min, it was diluted withCHCl3 (2 10 mL) and washed with water (10 mL), NaHCO3 solution(10 mL) and brine (10 mL). The organic layers were dried over anhydrous sodium sulfate, evaporated and the residue purified by column chromatography using 30% ethyl acetate in pet. ether to afford corresponding amides 8a-i, 9a-e and 10a-h.

According to the analysis of related databases, 5071-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Doma, Anuradha; Kulkarni, Ravindra; Palakodety, Radhakrishna; Sastry, G. Narahari; Sridhara, Janardhan; Garlapati, Achaiah; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 6209 – 6219;,
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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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

To a solution of methyl 1-methyl-4-nitro-pyrazole-3-carboxylate (2 g, 10.8 mmol, CAS400877-57-8) in MeOH (20 mL) was added Pd/C (200 mg, 10% wt) under N2 atmosphere. The suspension was degassed and purged with H2 gas 3 times. The mixture was stirred under H2 (15 Psi) at rt for 12 hr. On completion, the reaction mixture was filtered and concentrated in vacuo to give the title compound (1.68 g, 100% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta 6.95 (s, 1H), 3.92 (s, 3H), 3.86 (s, 3H).

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 400877-57-8.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics