Day: August 12, 2021

Reference of 1904-31-0, These common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-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.

To a stirred suspension of 1-methyl-1H-pyrazol-3-amine 76a (0.5 g, 5.1 mmol) in toluene (20 mL) in an round bottom flask fitted with Dean-Stark apparatus was charged with hexane-2,5-dione (0.70 g, 6.1 mmol) followed by p-toluene sulfonic acid (0.097 g, 0.51 mmol) and the reaction mixture was heated at 115°C for about 6 h. The reaction mixture was cooled to room temperature. Reaction mass was concentrated fully under reduced pressure, residue obtained was dissolved in DCM, given water wash followed by brine wash, dried over Na2504 and concentrated under redcued pressure to obtain 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole 76b (0.55 g, 55percent yield) as green oil. 1HNMR (400 MHz, CDC13): 6 7.39 (d, 111), 6.15 (s, 1H), 5.85 (s, 2H), 3.92 (s, 3H), 2.10 (s, 6H), MS: 176.11 (M+H).

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 92933-47-6, name is 5-Isopropyl-1H-pyrazole-3-carboxylic acid, molecular formula is C7H10N2O2, 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: 92933-47-6

General procedure: The aqueous solution of Eu(NO3)3.6H2O (1mmol) was treated with threefold excess of ethanolic solution of HIPA (3mmol) and the resulting mixture was thoroughly mixed on magnetic stirrer. The aqueous solution of NaOH was added drop wise to adjust the pH of mixture by 6-7. After constant stirring of 3 hr, off white precipitates of C1 binary complex were appeared which were isolated by vacuum filtration, washed with ethanol and water respectively, and then dried in desiccators.[19] Similarly, ternary complexes C2-C5 were synthesized by adding ethanolic solution of dmbipy, dipy, dmph and phen (1mmol) respectively, to the reaction mixture of europium(III) nitrate (1mmol) and ligand HIPA (3mmol) prior to adjustment of pH of the solution. Binary complex of gadolinium ion with ligand HIPA [Gd(IPA)3.2H2O] is synthesized by similar method as of C1 to calculate the triplet state of ligand. The synthetic routes of ligand HIPA and europium (III) complexes C1-C5 are shown in Fig. 1. Eu(IPA)3.2H2O (C1): light pink powder, yield 71%; IR: cm1 3450 (s), 3180 (s), 3090 (s), 2961 (s), 2371 (w), 1644 (s), 1507 (w), 1411 (m), 1301 (s), 1250 (s), 1019 (m), 840 (m), 814 (m), 780 (m), 651 (w), 566 (w), 497 (w), 428 (w).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 92933-47-6, its application will become more common.

Reference:
Article; Dhankhar, Priyanka; Bedi, Manisha; Khanagwal, Jyoti; Taxak, Vinod B.; Khatkar, Satyender P.; Doon, Priti Boora; Spectroscopy Letters; vol. 53; 4; (2020); p. 256 – 269;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 4058-91-7, These common heterocyclic compound, 4058-91-7, name is 5-Amino-1-methyl-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.

0.47g first After completion of the reaction, first substitution reaction 3h; after completion 0 C of the dropwise addition, 10 ml cooling, circulating water, and vacuum distillation, to obtain a yellow viscous solid, namely second intermediate (1 – methyl -5 – amino – 111H-pyraz -4 -benzoyl chloride); after completion of the dropwise addition reaction, is carried out under stirring.

Statistics shows that 5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 4058-91-7.

Reference:
Patent; Nankai University; Li Huabin; Li Luyang; Gu Jian; Kuang Xinyi; Xia Zhe; Zhang Shangzhong; Guo Lihui; Chen Rui; (16 pag.)CN110066282; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 14521-81-4, The chemical industry reduces the impact on the environment during synthesis 14521-81-4, name is 3-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A mixture of (5)-S -chloro-N-( 1 -cyclopropyl-2,2,2-trifluoroethyl)-7-methylpyrazolo[ 1,5 -aj pyrimidine-3 -carboxamide (70 mg, 0.21 mmol), 3-fluoro- 1H-pyrazole(18 mg, 0.21 mmol), and K2C03 (58 mg, 0.42 mmol) in DMF (2 mL) was stirred at 60 C for 2 h, poured into H20 (10 mL), and extracted with EA (30 mL x 3). The combined organic phases were washed with H20 (50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel columnchromatography (PE/EA = 2/1) and preparative HPLC (10 mM NH4HCO3/MeCN) to afford thetitle compound (14 mg, 24%) as a white solid. ?H NMR (400 MHz, MeOD-d4): 5 8.59 (s, 1H),8.55 (t, J= 2.4 Hz, 1H), 7.65 (s, 1H), 7.44 (q, J= 2.8 Hz, 1H), 4.36-4.30 (m, 1H), 2.92 (s, 3H),1.40-1.34 (m, 1H), 0. 82-0.75 (m, 1H), 0.70-0.58 (m, 2H), 0.52-0.46 (m, 1H). LC-MS m/z:383.1 [M+Hj. HPLC: Purity (214 nm): 93%; tR= 8.83 min.

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-Fluoro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GOOD, Andrew, C.; (391 pag.)WO2017/176960; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-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. SDS of cas: 39806-90-1

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

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

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 181585-93-3, The chemical industry reduces the impact on the environment during synthesis 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

5-Nitro-3-pyrazole-carboxylic acid methyl ester (22.35 g, 130.61 mmol) is dissolved in each 160 mL THF und glacial acetic acid. Then, Pd-C (10%, 4.36 g) are added and the reaction is stirred for 6 days under hydrogen atmosphere at RT. Then, the mixture is filtered over celite and the solvent is removed under vacuum. The crude material is dissolved in methylene chloride (800 mL) and sodium hydrogen carbonate (200 g) are added, filtered and the solvent is again removed under vacuum. This procedure is repeated until the acetic acid smell is lost. 5-Amino-3-pyrazole-carboxylic acid methyl ester is isolated in high yields (16.91 g, 91.7%).

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

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; US2008/32998; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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. COA of Formula: C3H3IN2

INTERMEDIATE 18 3 -Fluoro-4-(3 -iodo- 1 H-pyrazol- 1 – vDpyridine To a solution of 3-iodopyrazole (0.70 g, 3.61 mmol) in DMSO (15.1 mL) was added sodium hydride (60% in oil, 0.159 g, 3.97 mmol) and stirred for 0.5 h before 3,4- difluoro pyridine (0.415 g, 3.61 mmol) was added. The reaction mixture was stirred at 90 C for 2.5 h. The reaction was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 40 g, 0-20 % EtOAc in hexanes) to give 3- fluoro-4-(3-iodo-lH-pyrazol-l-yl)pyridine, as a white solid. LCMS calc. = 289.95; found = 289.92 (M+H)+. NMR (500 MHz, CDC13): delta 8.61 (d, J= 3.8 Hz, 1 H); 8.48 (d, J= 5.4 Hz, 1 H); 8.02 (d, J= 2.4 Hz, 1 H); 8.00 (d, J= 5.4 Hz, 1 H); 6.70 (d, J= 2.5 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4522-35-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 368870-03-5, 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. 368870-03-5, name is (4-(1H-Pyrazol-1-yl)phenyl)methanamine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-(Pyrazol-1-yl)benzylamine (12.2 g, 0.07 mol) was dissolved in 50 mL of 2-methoxyethanol (75 mL) and 3-isopropyl-pyrimidine-5,7-dithiol (2) (13.3 g, 0.059 mol) was added under an atmosphere of nitrogen. The reaction mixture was heated at 120 C for 12 hours. The reaction product crystallized upon cooling to 10-15 C and was filtered off. After washing with 2-methoxyethanol, then THF, and drying in vacuo at 75 C, 13.7 g of product are obtained in 62% yield. The analytical sample was recrystallized from DMS0/H20, dried at 75 C under vacuum; m.p. 268-270 C (decomposition), UV (nm): 268 l, 288 l, 300 l, 336 l?. MS ESI+ 366.1 (M+H)+, ESI- 364.1 (M-H) . NMR (500 MHz; DMSO-d6): 1.23 (d, / = 7.03 Hz, 6H, -CH(C//3)2); 3.44 (bs, 1H, -C//(CH3)2); 4.75 (d, J = 6.11 Hz, 2H, -NH-G-); 6.50-6.51 (m, 1H, HAT); 7.46 (d, / = 7.95 Hz, 2H, HAT); 7.71 (d, / = 1.53 Hz, 1H, HAT); 7.79 (d, J = 8.25 Hz, 2H, HAT) ; 8.45 (d, J = 2.45 Hz, 1H, HAT) ; 9.17 (bs, 1H, -NH-); l2.23(bs, 1H, -NH); 13.74 (bs, 1H, -SH). 13C (125 MHz; DMSO-d6): 21.8; 42.4; 107.7; 118.3; 127.6; 128.7; 138.7; 140.8. Anal. (CI8H19N7S) C, H, N, S.

The synthetic route of (4-(1H-Pyrazol-1-yl)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERZITA PALACKEHO V OLOMOUCI; USTAV EXPERIMENTALNI BOTANIKY AV CR, V.V.I.; HAVLICEK, Libor; STURC, Antonin; REZNICKOVA, Eva; JORDA, Radek; KRYSTOF, Vladimir; STRNAD, Miroslav; (66 pag.)WO2019/149295; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 82668-50-6, 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. 82668-50-6, name is Ethyl 2-(3-Pyrazolyl)acetate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(1H-pyrazol-3-yl)acetate (180 mg, 1.17 mmol), caesium carbonate (762 mg, 2.34 mmol) and N,N-dimethylformamide (2 mL) were added in a 25 mL single-neck flask. After cooling in an ice bath, methyl iodide (332 mg, 2.34 mmol) was added dropwise, and the reaction was continued for 2 hours in an ice bath. After completion of the reaction monitored by TLC, water (20 mL) was added. Then mixture was extracted with ethyl acetate (3?10 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. Solvent was removed in vacuo to afford a mixture of ethyl 2-(1-methyl-1H-pyrazol-3-yl)acetate and ethyl 2-(1-methyl-1H-pyrazol-5-yl)acetate (yellow oil, 136 mg). Step 5: 2-(1-Methyl-1H-pyrazol-5-yl)acetic acid and 2-(1-methyl-1H-pyrazol-3-yl)acetic acid (0079) The mixture of ethyl 2-(1-methyl-1H-pyrazol-3-yl)acetate and ethyl 2-(1-methyl-1H-pyrazol-5-yl)acetate (136 mg, 0.81 mmol), lithium hydroxide monohydrate (102 mg, 2.43 mmol) and ethanol/H2O (2 mL/0.5 mL) were added in a 25 mL single-neck flask, and the mixture was reacted at room temperature for 0.5 hour. After completion of the reaction, ethanol was removed under reduced pressure, then water (2 mL) was added. The mixture was adjusted to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate (3 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to remove the solvent to give a product (yellow oil, 100 mg). Step 6: Synthesis of N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-3-yl)acetami de (9A) and N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)acetami de (9B) (0080) 4′-Amino-2′,6′-dichloro-4-isobutyl-[1,1′-biphenyl]-3-carbonitrile (40 mg, 0.13 mmol), the mixture of 2-(1-methyl-1H-pyrazol-5-yl)acetic acid and 2-(1-methyl-1H-pyrazol-3-yl)acetic acid (44 mg, 0.32 mmol), HATU (118 mg, 0.38 mmol), N,N-diisopropylethylamine (50 mg, 0.39 mmol) and dichloromethane (2 mL) were added in a 25 mL single-neck flask, and the mixture was reacted at room temperature for 4 hours. The resulting crude product was separated by preparative thin layer chromatography (petroleum ether: ethyl acetate = 1:1) to give N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-3-yl)acetami de (white aolid, 26 mg), 1H NMR (400 MHz, CDCl3) delta 9.23 (s, 1H), 7.66 (s, 2H), 7.47 (s, 1H), 7.33 (t, J = 7.4 Hz, 4H), 6.19 (s, 1H), 3.93 (s, 3H), 3.75 (s, 2H), 2.75 (d, J = 7.3 Hz, 2H), 2.02 – 1.97 (m, 1H), 0.97 (d, J = 6.6 Hz, 6H). MS (ESI) m/z: 441.0 (M+1) and N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)acetami de (white aolid, 27 mg), 1H NMR (400 MHz, CDCl3) delta 8.26 (s, 1H), 7.63 (s, 2H), 7.47 (d, J = 3.3 Hz, 2H), 7.34 (s, 2H), 6.26 (s, 1H), 3.87 (s, 3H), 3.80 (s, 2H), 2.75 (d, J = 7.3 Hz, 2H), 1.97 – 1.88 (m, 1H), 0.97 (d, J = 6.6 Hz, 6H). MS (ESI) m/z: 440.9 (M+1).

The synthetic route of Ethyl 2-(3-Pyrazolyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); 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. 180207-57-2, name is 2-(1H-Pyrazol-4-yl)ethanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H8N2O

General procedure: To a mixture of 3,6-dichloropyridazine (3.73 g, 25 mmol), 4(5)-Hydroxymethylimidazole (1.96 g, 20 mmol), and Cs2CO3 (8.14 g, 25 mmol) was added acetonitrile (80 mL). The mixture was refluxed for 3 h and was poured into H2O (200 mL). 1N HCl(aq) was added slowly until the pH is ca. 7-8. Then the aqueous layer was extracted with EtOAc (150 mL) and then CH2Cl2 (100 mL x 5). The combined organic layer was dried (Na2SO4) and filtered. After removal of solvent, the product was triturated with 10% CH2Cl2/Et2O (30 mL x 3) to give 1.74 g of product. The filtrate was concentrated and was purified by column using 60-70-80% EtOAc/(CH2Cl2/hexane=1/1) as the eluent to give 629 mg of prouct. Total 2.36g of D (53%) was obtained.

The synthetic route of 180207-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Shyh-Ming; Tang, Yuting; Rano, Thomas; Lu, Huajun; Kuo, Gee-Hong; Gaul, Michael D.; Li, Yaxin; Ho, George; Lang, Wensheng; Conway, James G.; Liang, Yin; Lenhard, James M.; Demarest, Keith T.; Murray, William V.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 5; (2014); p. 1437 – 1441;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics