Day: August 26, 2021

Some common heterocyclic compound, 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. Quality Control of 1-Methyl-1H-pyrazole-3-sulfonyl chloride

Ui) l-Methyl-lH-pyrazole-3-sulfonic acid benzyl-(l-oxo-l,2,3,4-tetrahydro- isoquinolin-6-yl)-amideTo a stirred solution of 6-benzylamino-3,4-dihydro-2H-isoquinolin-l-one (45 mg, 0.18 mmol) and pyridine (31 mul, 0.39 mmol) in anhydrous acetonitrile (1 ml) was added 1- methyl-lH-pyrazole-3-sulfonyl chloride (70 mg, 0.39 mmol) and the reaction heated to 1500C in a microwave for 0.5 hrs. The solvent was evaporated in vacuo and the crude residue purified by preparative tic (5% methanol in dichloromethane) to afford the title compound as a yellow solid (10 mg, 14%). HPLC retention time 3.83 min. Mass spectrum (ES+) m/z 397 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 89501-90-6, its application will become more common.

Reference:
Patent; XENTION LIMITED; HAMLYN, Richard, John; MADGE, David; MULLA, Mushtaq; WO2010/139953; (2010); 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 139756-02-8

To a 250 ml three-mouth bottle by adding 2 – ethoxy formaldehyde 7.63 g, 1 – methyl -3 – propyl -4 – amino pyrazole -5 – carboxamide 9.6 g and isopropyl alcohol 150 ml, stir at room temperature 3 hours; adding 8.56 g anhydrous ferric trichloride, stirring which separate the reaction system access oxygen, temperature 60 C reaction 3 hours; boil off isopropanol about 100 ml, adding 180 ml purified water, filtered, drying to obtain the solid 14.8 g. Yield: 92.8%.

The synthetic route of 139756-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Tongjuan Pharmaceutical Technology Co., Ltd.; Zheng Qingquan; Huang Shifu; Cao Xutao; Li Yongjian; (10 pag.)CN104804003; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 52222-73-8, 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. 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a room temperature solution of C5 (100 mg, 0.208 mmol) in N,N-dimethylformamide (2 mL) was added cesium carbonate (170 mg, 0.522 mmol), followed by 4-(trifluoromethyl)-1H-pyrazole (42.5 mg, 0.312 mmol), and the reaction mixture was stirred at 80 C. overnight. It was then partitioned between water and ethyl acetate, and the aqueous layer was extracted with ethyl acetate (3*15 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 25% ethyl acetate in heptane) provided the product as an oil. Yield: 71 mg, 0.13 mmol, 62%. LCMS m/z 536.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.74 (s, 1H), 7.69 (s, 1H), 7.25 (br d, J=8.6 Hz, 2H), 6.88 (br d, J=8.6 Hz, 2H), 5.54-5.44 (m, 1H), 4.78 (quint, J=8.4 Hz, 1H), 4.51 (AB quartet, JAB=11.7 Hz, DeltanuAB=28.5 Hz, 2H), 3.81 (s, 3H), 3.76 (dd, half of ABX pattern, J=11.3, 3.9 Hz, 1H), 3.69 (br dd, half of ABX pattern, J=10.9, 7.0 Hz, 1H), 3.55-3.47 (br m, 2H), 3.47-3.38 (br m, 2H), 2.52-2.42 (m, 2H), 2.38 (dd, half of ABX pattern, J=12.5, 8.6 Hz, 2H), 1.76-1.62 (br m, 4H).

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-(Trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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 152120-54-2, Safety of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

To a solution of 2-(benzyloxycarbonylamino)ethoxyamine (780 mg, 3.7 mmol), as prepared in the preceding step, in N,N-dimethylformamide (20 mL) was added [N,N’-di(tert-butoxycarbonyl)]amidinopyrazole (1.25 g, 4.0 mmol). The mixture was stirred at room temperature overnight, and the solvent evaporated under high vacuum. The residue was purified by flash column chromatography (0-5% ethyl acetate in methylene chloride) to give the title compound as a colorless oil (1.55 g, 93%). 1H-NMR (300 MHz, CDCl3) delta 9.08 (s, 1H), 7.67 (s, 1H), 7.33 (m, 5H), 6.21 (br s, 1H), 5.21 (br s, 1H), 5.11 (s, 2H), 4.12 (t, J=4.8 Hz, 2H), 3.54 (q, J=4.9 Hz, 2H), 1.49 (s, 9H), 1.46 (s, 9H).

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:
Patent; Kreutter, Kevin D.; Lee, Lily; Lu, Tianbao; Mohan, Venkatraman; Patel, Sharmila; Huang, Hui; Xu, Guozhang; Fitzgerald, Mark; US2004/254166; (2004); A1;,
Pyrazole – Wikipedia,
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. 50877-42-4, name is 1-Benzyl-4-iodo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 50877-42-4

b) 1 -Benzyl- 1 H -pyrazole-4 -carbaldehyde (A 148) 1-Benzyl-4-iodo-1 H-pyrazole A147 (859 mg, 3.02 mmol) in THF (5 mL) was cooled to 0 C under nitrogen before a 2.0 M solution of isopropylmagnesium chloride in THF (1.66 mL, 3.33 mmol) was added. After 1 hour, DMF (0.5 mL) was added. The mixture was stirred for 30 minutes at 0 C then a further 30 minutes at room temperature. The mixture was quenched with a saturated aqueous solution of ammonium chloride (10 mL), diluted with water (20 mL) and extracted with CHCI3 (3 chi 25 mL). The pooled organics were washed with brine (50 mL), dried with sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography (12 g Si02 cartridge, 0-50% EtOAc in hexanes) to give the title compound as a colourless oil (170 mg, 30%). H NMR (400 MHz, CDCI3) delta 9.83 (s, 1 H), 8.00 (s, 1 H), 7.88 (s, 1 H), 7.42-7.33 (m, 3H), 7.29-7.25 (m, 2H), 5.33 (s, 2H). LCMS-B: rt 3.10 min, m/z (positive ion) 187.1 [M+H]+.

According to the analysis of related databases, 50877-42-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; STUPPLE, Paul Anthony; WALKER, Scott Raymond; PINSON, Jo-Anne; LAGIAKOS, Helen Rachel; LUNNISS, Gillian Elizabeth; HOLMES, Ian Peter; STUPPLE, Alexandra Elizabeth; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; KERSTEN, Wilhelmus Johannes Antonius; CAMERINO, Michelle Ang; WO2014/128465; (2014); A1;,
Pyrazole – Wikipedia,
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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1192-21-8

A magnetically stirred solution of amine 5 (10.0 g, 103 mmol) inTHF (250 mL) was treated with potassium tert-butoxide (23.0 g,205 mmol) at 0 C. The resultant suspension was brought to roomtemperature and stirred for 1 h before the dropwise addition of ofluoronitrobenzene(12 mL, 113 mmol). The reaction mixture wasstirred for 3 h, quenched with water (300 mL) and extracted withEtOAc (3 150 mL). The combined organic extracts were dried(MgSO4), filtered and concentrated under reduced pressure. Thecrude oil was purified by flash column chromatography (silica, 3:5v/v EtOAc:hexanes) and concentration of the relevant fractions(Rf 0.42 in 1:1 v/v EtOAc:hexanes) afforded the title compound(16.9 g, 77percent) as yellow crystals.1H NMR (300 MHz, Chloroform-d): d 9.11 (s, 1H, NH), 8.25 (d,J 8.1 Hz, 1H), 7.56e7.54 (m, 1H), 7.52e7.38 (m, 1H), 6.96e6.84 (m,1H), 6.78e6.74 (m, 1H), 6.20 (d, J 2.5 Hz, 1H), 3.76 (s, 3H). 13C NMR(75 MHz, Chloroform-d): d 142.7, 139.0, 136.8, 136.3, 133.4, 126.6,118.7, 115.8, 101.8, 35.2. IR (diamond cell, neat) nmax: 3297, 3094,1609, 1572, 1509, 1490, 1340, 1221, 1145, 1075, 1043, 927, 750 cm1.LRMS (ESI) m/z: 219 ([MH], 100percent). HRMS (ESI) Found:(MNa), 241.0697. C10H10N4O2 requires (MNa), 241.0696. MP:133e135 C.

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 1192-21-8.

Reference:
Article; Jorgensen, William T.; Gulliver, Damien W.; Katte, Timothy A.; Werry, Eryn L.; Reekie, Tristan A.; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1644 – 1656;,
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. 478968-48-8, name is Ethyl 3-methoxy-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C7H10N2O3

(6-{3-Azabicyclo[3. 1 .0]hexan-3-yl}-2-methylpyridin-3-yl)methanol (410 mg), tributylphosphine (595 pL) and ethyl 3- methoxy-1H-pyrazole-4-carboxylate (340 mg) are dissolved in tetrahydrofuran (10 mL), cooled to -10 00 and treated with di-tert.-butyl azodicarboxylate (DBAD, 510 mg). Then the mixture is stirred for 30 minutes at room temperature. The mixture is purified by HPLC on reversed phase (acetonitrile, water, ammonia) to give the title compound.LC (Method 8): tR = 1.09 mm; Mass spectrum (ESIj: mlz = 357 [M+H].

The synthetic route of 478968-48-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; LINGARD, Iain; HAMPRECHT, Dieter, Wolfgang; BAKKER, Remko, Alexander; ECKHARDT, Matthias; GOLLNER, Andreas; HEHN, Joerg, P.; LANGKOPF, Elke; WAGNER, Holger; WELLENZOHN, Bernd; WIEDENMAYER, Dieter; (90 pag.)WO2018/192866; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 35100-92-6,Some common heterocyclic compound, 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, molecular formula is C5H9N3, 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 benzoic acid which was obtained by hydrolysis of methyl esters 8 or 12A-E (0.22 mmol, 1.0 equiv), aminothiazole or imidazo[1,2-a]pyrazin-8-amine or aminopyrazole (0.33 mmol, 1.5 equiv), HATU (0.33 mmol, 1.5 equiv) and HOAt (0.33 mmol, 1.5 equiv) in DMF (2 mL) was added dropwise di(isopropyl)ethylamine (DIPEA) (0.12 mL, 0.67 mmol, 3 equiv). The reaction was run under microwave at 60 C (40 W) for 30 min, and then cooled to room temperature and poured into brine. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous NaSO4 and concentrated. The residue was purified by chromatography (SiO2, petroleum ether/EtOAc = 4:1-1:1) to yield corresponding amides as white or yellow powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Dimethyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Article; Mao, Weiwei; Ning, Mengmeng; Liu, Zhiqing; Zhu, Qingzhang; Leng, Ying; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2982 – 2991;,
Pyrazole – Wikipedia,
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. 706819-66-1, name is 2-Bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H7BrN2O

2-bromo-1-(1-methyl-1H-pyrazol-4-yl)-ethanone (0.5 g; 2.46 mmol) in DMF (10 mL) were added to potassium phtalimide (0.46 g; 2.46 mmol). The reaction mixture wasstirred at RT for 5h, poured into water-ice and EtOAc was added. The organic layer was separated, washed with water, brine, dried over Mg504, filtered and evaporated till dryness. The residue was purified by chromatography over silica gel (irregular SiOH 15-40.im, 24g; mobile phase: 97% DCM, 3% MeOH (+10% NH4OH)). The pure fractions were collected and evaporated to dryness yielding 460 mg (69%) of intermediate 86.

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 706819-66-1.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82560-12-1, These common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, 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.

3-(tert-butyl)-lH-pyrazole-5-amine (503 mg, 3.61 mmol), Intermediate 30b (915 mg, 3.44 mmol), copper (I) iodide (32.8 mg, 0.172 mmol), trans- N,N’-dimethylcyclohexane- l ,2-diamine (97.8 mg, 0.688 mmol) and K2CO3 (998 mg, 7.22 mmol) were weighed in a round bottom flask, sealed with a septum and evacuated and purged with Ar 3 times. Xylene (4 ml, sparged with Ar for 45 min), was then introduced to the flask and the brown suspension was heated to 150C for 90 min. The reaction was cooled, diluted with EtOAc (10 mL), water (10 mL) and saturated aqueous NH4OH solution (5 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL), and the combined organics washed with brine (15 mL), dried over Na2SO4, filtered, concentrated in vacuo and subjected to FCC eluting with 0 – 4% MeOH/EtOAc to afford the title compound as a pale yellow solid (457 mg, 48%). LCMS (Method 4): Rt 2.81 min, m/z 278 [MH+].

Statistics shows that 3-Amino-5-tert-butylpyrazole is playing an increasingly important role. we look forward to future research findings about 82560-12-1.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; PANCHAL, Terry Aaron; JENNINGS, Andrew Stephen Robert; CRIDLAND, Andrew Peter; HURLEY, Christopher; WO2014/194956; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics