Day: May 25, 2021

920006-32-2, name is 1-Isopropylpyrazole-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. Quality Control of 1-Isopropylpyrazole-5-carboxylic Acid

DIPEA (94 pL, 0.57 mmol) was added to a stirred solution of Intermediate 56 (70 mg, 0.19 mmol), 1 -(propan-2-yl)- 17/-pyrazolc-5-carboxylic acid (44 mg, 0.28 mmol) and HATU (112 mg, 0.29 mmol) in DCM (2.5 mL) at r.t. The reaction mixture was stirred at r.t. for 18 h, then diluted with water (5 mL) and extracted with DCM (3 x 15 mL). The combined organic phases were separated using a hydrophobic PTLE frit, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, using a gradient of fc/7-butyl methyl ether in heptane (0-80%), to afford the title compound (61 mg, 65%) as a white solid. 5H (250 MHz, DMSO-de) 10.12 (s, 1H), 8.45 (d, J8.2 Hz,1H), 7.70-7.66 (m, 1H), 7.50 (d, 1.9 Hz, 1H), 7.43-7.33 (m, 2H), 7.12 (d, J5.6 Hz, 1H), 6.95 (d, 2.0 Hz, 1H), 6.81 (d, J5.7 Hz, 1H), 5.44-5.34 (m, 1H), 4.37 (t, j 8.5 Hz, 1H), 3.99-3.90 (m, 2H), 3.77-3.67 (m, 2H), 2.11-2.01 (m, 2H), 1.91-1.75 (m, 2H), 1.74-1.65(m, 2H), 1.63-1.56 (m, 1H), l.37 (d, 6.6 Hz, 3H), 1.34 (d, J6.6 Hz, 3H), 1.32-1.26 (m, 1H), 1.25-1.18 (m, 1H), 1.16-1.10 (m, 2H), 1.10-1.01 (m, 1H), 0.92-0.81 (m, 5H). uPLC- MS (method 1): MH+ m/z 491, RT 4.06 minutes.

The synthetic route of 920006-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SRL; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; FOULKES, Gregory; LECOMTE, Fabien Claude; (0 pag.)WO2020/11731; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 113808-86-9, 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. 113808-86-9, name is 3,5-Dimethylpyrazole-4-carboxylic Acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 11; [4-(5-{3-[(1-Acetyl-piperidine-4-carbonyl)-(3-chloro-4-methyl-phenyl)-amino]-propyl}-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-3,5-dimethyl-pyrazol-1-yl]-acetic acid trifluoro acetate (II-18); step 1-; A mixture of 3,5-dimethyl-1H-pyrazole-4-carboxylic acid (820 mg; CAS Reg No. 113808-86-9), 11a (2.42 g), TEA (2.2 mL) and PyBOP (5.84 g) in DMF (15 mL) was stirred at RT overnight. The reaction was quenched by addition of water and partitioned between water and EtOAc. The organic layer was separated and washed 3 times with water and once with brine, dried (MgSO4), filtered and evaporated. The residue was purified via SiO2 chromatography eluting with DCM/MeOH/NH4OH to afford 0.829 g of 62a.

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, 3,5-Dimethylpyrazole-4-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lemoine, Remy; Melville, Chris Richard; Rotstein, David Mark; Wanner, Jutta; US2007/191335; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 39846-84-9, name is Ethyl 5-nitro-1H-pyrazole-3-carboxylate, 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. Computed Properties of C6H7N3O4

Zinc powder (50 g, 765 mmol) was added portion-wise at 0 C to a solution of ethyl 5-nitro-1H- pyrazole-3-carboxylate (10 g, 53.5 mmol) in acetic acid (100 mL) and water (20 mL). The resulting mixture was stirred to rt for 3 h, then filtered and the pH of the filtrate was adjusted to 8 with ammonium hydroxde and extracted with EtOAc (2 x 500 mL). The combined organic layers dried over Na2S04 and concentrated which gave the title compound (6 g, 53%) as a solid. The compound was used in next step without further purification. MS (ES+) 156.11 [M+H]+.

The synthetic route of Ethyl 5-nitro-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 920006-32-2, These common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-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.

tert-Butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (240 mg, 0.67 mmol) obtained in Example 145-E) was dissolved in 12M hydrochloric acid (1 mL) and ethanol (1 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, basified with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF (2 mL), 1-(1-methylethyl)-1H-pyrazole-5-carboxylic acid (104 mg, 0.67mmol)), HATU (307 mg, 0.81 mmol) and DIEA (0.058 mL, 0.34 mmol) were added at room temperature, and the mixture was stirred at 60C for 3 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (90:10-50:50)] to give the title compound (130 mg) as a pale-brown powder (yield 49%). MS (ESI+): [M+H]+ 393. 1H NMR (300 MHz, CDCl3) delta 1.51 (6H, d, J = 6.8 Hz), 2.40 (3H, s), 4.20 (2H, s), 5.30-5.65 (1H, m), 6.64 (1H, d, J = 2.3 Hz), 6.87-7.05 (2H, m), 7.11 (1H, s), 7.57 (1H d, J = 1.9 Hz), 7.72 (1H, brs).

The synthetic route of 920006-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 657428-42-7, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate, molecular formula is C10H15N3O2, 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

Intermediate 5; 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole; Step A: tert-Butyl 1-(methylsulfonyl)]-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (A) and tent-butyl 2-(methylsulfonyl)]-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (B); A suspension of N-Boc-pyrazolopyrrolidine (Intermediate 3, Step B) (27.16 g, 130 mmol) in anhydrous acetonitrile (1.0 L) was charged in a 2.0 L three-neck flask fitted with a thermometer and an addition funnel and then treated with sodium hydride (60% dispersion in oil, 6.23 g, 156 mmol) while under nitrogen atmosphere in one portion. The reaction mixture was stirred at room temperature for 2 h. The resulting white suspension was then cooled in an ice bath and methanesulfonyl chloride (25.2 mL, 324 mmol) was slowly added via addition funnel The ice bath was then removed and the mixture was stirred 1 h at room temperature. The reaction mixture was quenched with water (500 mL) and the layers were separated. The aqueous layer was then extracted with 2×500 mL of dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give a mixture of products A and B as colorless syrups. NMR in CD3OD indicated a 1:1 mixture of two products, in which the proton on the pyrazole ring in product A appeared at 7.70 ppm while the proton in product B appeared at 7.95 pm. LC-MS: 288.08 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 657428-42-7, its application will become more common.

Reference:
Patent; Biftu, Tesfaye; Chen, Ping; Cox, Jason M.; Weber, Ann E.; US2010/120863; (2010); 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. 70817-26-4, name is (1-Phenyl-1H-pyrazol-4-yl)methanol, A new synthetic method of this compound is introduced below., SDS of cas: 70817-26-4

(1 -Phenyl- lH-pyrazol-4-yl)~methanol (2 g) in dichloromethane (15 mL) was treated with thionyl chloride (10 mL) and the mixture stirred at 200C for Ih. The resulting suspension was diluted with wA¸hexane (15 mL) and the solid collected by filtration to afford the subtitled compound as an off-white solid (1.120 g).1H NMR (400 MHz, CDCl3) I’ 8.61 (IH, s), 7.84 – 7.80 (3H, m), 7.53 – 7.47 (2H, m), 7.35 7.30 (IH, m), 4.77 (2H, 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; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2009/153536; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, molecular formula is C6H9BrN2, 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. name: 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole

General procedure: The phenanthridine skeletons1-8 (0.1 mmol) were dissolved in dryTHF (10 mL), and NaH (50 mg, 2 mmol), and 3-(bromomethyl)pyridine,3-(chloromethyl)-1,5-dimethyl-1H-pyrazole or 5-bromomethyl-1,3-dimethyl-1H-pyrazole (1 mmol) were added. The mixture was stirred atrt. for 12 h and quenched with H2O (50 mL) in an ice bath. The solutionwas evaporated to remove the THF and extracted with CH2Cl2(2×30 mL). The organic layer was washed with saturated NaHCO3 andbrine, dried over MgSO4, filtered and concentrated. The residue waspurified by column chromatography using petroleum-EtOAc as theeluent to afford about 35 mg of each phenanthridine compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 873191-23-2, its application will become more common.

Reference:
Article; Chen, Duo-zhi; Yang, Bi-juan; He, Xiao-li; Fan, Shi-rui; Cai, Jie-yun; Jing, Chen-xu; Zhang, Heng; Zhang, Yu; Li, Lin; Hao, Xiao-jiang; Bioorganic Chemistry; vol. 84; (2019); p. 285 – 294;,
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. 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, A new synthetic method of this compound is introduced below., name: 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole

General procedure: To a cooled solution of compound 6 (361.0 mg, 1 mmol) in DMF (10 mL) was added NaH (60% in oil, 48.0 mg, 1.2 mmol) carefully. The mixture was stirred at 0 C for 1h. A solution of R1X (X=Cl, Br; 1.2 mmol) in DMF (5 mL) was then added dropwise in the mixture. The mixture was heated to 40 C and stirred for 8-16 h. The reaction mixture was cooled and quenched at 0 C with a saturated NH4Cl aqueous solution. Then mixture was concentrated under vacuum to remove most of the DMF and re-dissolved with CH2Cl2. After filtering, the filtrate was washed with saturated NaCl aqueous solution, dried with MgSO4 and concentrated under vacuum. The crude material was purified by column chromatography (PE/EA) on silica gel to afford compound 6a-6r.

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; Chen, Peng; Zhang, Dianwen; Li, Meng; Wu, Qiong; Lam, Yuko P.Y.; Guo, Yan; Chen, Chen; Bai, Nan; Malhotra, Shipra; Li, Wei; O’Connor, Peter B.; Fu, Hongzheng; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 128694-63-3, A common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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 suspension of 6-(2-amino-5-chlorothiazol-4- yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.41 mmol) and 1 -methyl-3-(trifluoromethyl)- 1 H-pyrazole-5-carboxylic acid (0.087 g, 0.45 mmol), and pyridine (0.16 m E, 1.96 mmol) in acetonitrile (2.5 mE) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.61 mE, 1.02 mmol). The sealed tube was heated to 1000 C. for 16 hand the precipitation formed. Afier cooling, 1 -methyl-N-(4-(2-oxo-i ,2,3,4-tetrahydroquinolin-6-yl)thi- azol-2-yl)-3-(trifluoromethyl)-i H-pyrazole-5-carboxamide (0.160g, 93%). ?H NMR (400 MHz, DMSO-d): oe 12.97(bs, 1H), 10.20 (s, 1H), 7.74 (m, 1H), 7.71 (m, 1H), 7.59 (s, 1H),6.91 (d, 1H, J=8.0 Hz), 4.23 (s, 3H), 2.93 (t, 2H, J=7.2 Hz),2.48 (partial masked under d-DMSO, m, 2H); MS (ESI):Calcd. for C,8H,4F3N5025: 421, found 422 (M+i).

The synthetic route of 128694-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); 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. 821767-61-7, name is tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate

Tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate (CAS [821767-61-7]), (122 mg, 0.62 mmol) was added at 10 C, under N2 to a solution of intermediate 15 (183 mg, 0.55 mmol) in MeOH (7 mL). The mixture was stirred at rt for 5 h. Then NaBH4 (31 mg, 0.83 mmol) was added portionwise and the mixture was stirred at rt for 15 h. The mixture was poured into ice water, extracted with DCM. The organic layer was dried over MgSO4, filtered and evaporated to dryness giving 0.35g of crude compound. The residue was purified by chromatography over silica gel (Stationary phase: irregular SiOH 15-40mum 40g, Mobile phase: Gradient from 0.1% NH4OH, 97% DCM, 3% MeOH to 0.1% NH4OH, 95% DCM, 5% MeOH). The fractions containing product were collected and evaporated to dryness yielding 150 mg (yield 39%) of intermediate 17.

The synthetic route of 821767-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron, Nathaniel; PILATTE, Isabelle, Noelle, Constance; (157 pag.)WO2018/109088; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics