Tag: M.W:100-200

Application of 25016-12-0, 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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[0242] Bis(2-methoxyethyl)aminosulfurtrifluoride (3.71 ml, 20.14 mmol)was added to a stirred solution of l,3-dimethyl-lH-pyrazole-4-carbaldehyde (500 mg, 4.03 mmol) in DCM (6 ml) at 0 C. Then the mixture was stirred at room temperature for overnight. The reaction was quenched by NaHC03 solution (20 ml), extracted with dichloromethane (3 x lOmL). The combined organic fractions were washed with brine (3 x 10 ml), dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC reverse phase (C-8), eluting with (MeCN/H20=2/l), to give 4-(difluoromethyl)-l,3-dimethyl-lH- pyrazole as an oil. LC/MS = 147 [M+l].

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, 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUANG, Rongze; TING, Pauline; ALI, Amjad; WU, Heping; BERLIN, Michael; STAMFORD, Andrew; WANG, Hongwu; ZHOU, Gang; KIM, David; DENG, Qiaolin; LIM, Yeon-Hee; YU, Younong; (201 pag.)WO2016/81290; (2016); A1;,
Pyrazole – Wikipedia,
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Application of 92933-47-6, These common heterocyclic compound, 92933-47-6, name is 5-Isopropyl-1H-pyrazole-3-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.

General procedure: To a solution of HATU (104 mg, 0.27 mmol) and 3-isopropylpyrazole-5-carboxylic acid (36 mg, 0.22 mmol) in DMF (14 mL) was then added diisopropylethylamine (0.055 mL, 0.31 mmol). The reaction solution was stirred at room temperature for 2 h. 2-(Benzylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carbonitrile (75 mg, 0.21 mmol) was added in one portion. The solution was then stirred at room temperature overnight. The reaction was diluted with methylene chloride and washed. The aqueous layer was extracted with methylene chloride twice, the combined organic phases were dried over anhydrous MgSO4. The resulting residue was purified by column chromatography on silica gel (EtOAc/hexane = 2:1) to give title compound as a white solid (33 mg, 37%).

Statistics shows that 5-Isopropyl-1H-pyrazole-3-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 92933-47-6.

Reference:
Article; Nam, Mina; Kim, TaeHun; Kwak, Jinsook; Seo, Seon Hee; Ko, Min Kyung; Lim, Eun Jeong; Min, Sun-Joon; Cho, Yong Seo; Keum, Gyochang; Baek, Du-Jong; Lee, Jiyoun; Pae, Ae Nim; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 245 – 258;,
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Electric Literature of 112029-98-8,Some common heterocyclic compound, 112029-98-8, name is (1-Methyl-1H-pyrazol-4-yl)methanol, molecular formula is C5H8N2O, 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.

Step B 4-(methoxymethyl)-1-methyl-1,1-pyrazole To a suspension of sodium hydride (0.128 g, 3.21 mmol) in tetrahydrofuran (5 mL, 60 mmol) at 0° C. was added (1-methyl-1H-pyrazol-4-yl)methanol (0.300 g, 2.68 mmol) in tetrahydrofuran (2 mL, 20 mmol). The reaction was stirred at room temperature for 1 h, and then cooled down with ice bath. Methyl iodide (0.83 mL, 13 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was quenched with brine and extracted with EtOAc (3*). The combined organic phases were washed with water, brine, then dried over Na2SO4, and concentrated under reduced pressure to give 261 mg (77.2percent yield) of the desired product as colorless oil, which was directly used for the next reaction. LC/MS found: 127.2 (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 (1-Methyl-1H-pyrazol-4-yl)methanol, its application will become more common.

Reference:
Patent; Incyte Corporation; Huang, Taisheng; Feng, Hao; Kong, Lingquan; Wang, Anlai; Ye, Hai Fen; US2013/96144; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 49633-25-2,Some common heterocyclic compound, 49633-25-2, name is 3-Isopropylpyrazole, molecular formula is C6H10N2, 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 mixture of3-isopropyl-lH-pyrazole (3.74 g), 2- chloro-5-trifluoromethylpyridine (6.17 g) and N- methylpyrrolidone (18.7 ml) was addedNaOH (trademark: Tosoh pearl, 2.03 g) while stirring the mixture at room temperature. After reaction as it was for 9 hours, water (38 ml) and 6N hydrochloric acid (85 ml) were added, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane and then with toluene to give2- (3-isopropyl-lH-pyrazol-1-yl)-5- (trifluoromethyl) pyridine (6.94 g, yield 80%) as a colorless oil. H-NMR (CDC13)8 : 1.33 (6H, d, J=7.0 Hz), 3.0-3. 2(1H, m), 6.34(1H, d, J=2.5 Hz), 7.97(1H, dd, J=8.7, 2.1 Hz), 8.05(1H, d, J=8.7 Hz), 8.47(1H, d, J=2.5 Hz), 8.6-8. 7(1H, m).

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

Reference:
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2003/99793; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 612511-81-6,Some common heterocyclic compound, 612511-81-6, name is (1-Methyl-1H-pyrazol-3-yl)methanamine, 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.

To a solution of Oxirane intermediate (16.0 g, 52.56 mmol) in iPrOH (200 ml), was added (1-methyl-1 H-pyrazol-3-yl)methanamine (8.76 g, 78.84 mmol). The reaction mixture was stirred under 50°C for 16 h, after that RM was concentrated under reduced pressure and purified by silica column chromatography using 100percent ethyl acetate as eluent to give (8.8 g, 40 percent) as a thick liquid.

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

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; SHAMLOO, Mehrdad; JAHANGIR, Alam; YI, Bitna; EVANS, Andrew Kelley; GREEN, Michael John; (178 pag.)WO2017/197324; (2017); A1;,
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Application of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.

4.2.6 3,3′,5,5′-Tetrakis[(4-brom-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,2′,4,4′,6,6′-hexamethyldiphenylmethane (35) To a suspension of NaOH (192 mg, 4.81 mmol) in DMF (20 mL), 4-bromo-3,5-dimethyl-1H-pyrazole (841 mg, 4.81 mmol) (37) was added and stirred at room temperature for 20 min. After the addition of compound 20 (500 mg, 0.80 mmol) the reaction mixture was stirred for 72 h at room temperature. Afterwards, the mixture was poured into ice water (200 mL), the formed precipitate filtered off, washed thoroughly with distilled water and dried to constant mass in the desiccator. The desired compound 35 was obtained as a snow-white solid (750 mg, 94percent), mp 216 °C. 1H NMR (500 MHz, CDCl3): delta 5.17 (s, 8H), 4.18 (s, 2H), 2.19 (s, 6H), 2.12 (s, 12H), 2.05 (s, 12H), 2.01 (s, 12H) ppm. 13C NMR (CDCl3, 125 MHz): delta 145.52, 137.86, 137.12, 136.80, 135.81, 130.51, 94.17, 49.69, 33.36, 17.35, 16.53, 12.40, 10.35 ppm. MS (ESI): m/z 1000.8, 827.2, 681.0, 507.0, 333.0. Anal. Calcd for C43H52Br4N8: C, 51.62; H, 5.24; N, 11.20. Found: C, 51.39; H, 5.49; N, 11.38.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Koch, Niklas; Rosien, Jan-Ruven; Mazik, Monika; Tetrahedron; vol. 70; 45; (2014); p. 8758 – 8767;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, 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 5932-27-4, Product Details of 5932-27-4

To a solution of K2CO3 (94 mg, 0.66mmol) in DMF (8 mL) was added ethyl 1H-pyrazole-3-carboxylate (158 mg, 1.12 mmol). The mixture was stirred at 20 oC for 0.5 h under N2. Then to mixture was added a solution of A33 (100 mg, 0.22 mmol) in DMF (4 mL), and stirred at 20oC for 3 h. The mixture was diluted with EtOAc (50 mL), washed with brine (50mL*3) and the organic layer was dried over anhydrous Na2SO4, and then concentrated to give crude product. It was purification by column chromatography (petroleum ether: ethyl acetate = 4:1) to give the 40 (45 mg) as a yellow solid. 1H NMR (40): (400 MHz, CDCl3) delta 7.44 (d, J = 2 Hz, 1H), 6.87 (d, J = 2.4 Hz, 1H), 5.30 (s, 3H), 4.40 (dd, J =7.6 Hz, J =14.8 Hz, 2H), 3.96-3.91 (m, 1H), 3.60-3.53 (m, 1H), 3.47-3.38 (m , 2H), 2.60-2.52 (m, 1H), 2.21-2.11 (m, 1H), 2.07-2.00 (m, 1H), 1.90 -1.61 (m, 6H), 1.52-1.15 (m, 17H), 1.03 -0.92 (m, 4H), 0.82-0.72 (m, 1H), 0.66 (s, 3H)

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

Reference:
Patent; SAGE THERAPEUTICS, INC.; MARTINEZ BOTELLA, Gabriel; SALITURO, Francesco, G.; ROBICHAUD, Albert, Jean; HARRISON, Boyd, L.; (275 pag.)WO2016/61527; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 112029-98-8, name is (1-Methyl-1H-pyrazol-4-yl)methanol, 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: 112029-98-8

To a cooled solution of (1-methyl-1H-pyrazol-4-yl)-methanol (8.61 g, 0.076 mole) in DCM (100 mL) under N2 atmosphere, thionyl chloride (8.7 mL, 0.12 mole) was added drop wise. The reaction mixture was warmed to RT and stirred for 2 hours. The reaction mixture was concentrated under vacuum at 23 ? 25 °C to obtain the titlecompound.Yield: 12.77 g (99 percent); ?H – NMR (DMSO-d6, 400 MHz) oe ppm: 3.85 (s, 3H), 4.67 (s, 2H), 4.76 – 4.79 (t, 1H), 4.88 (bs, 1H), 7.47 (s, 1H), 7.78 (s, 1H).

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

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; SUBRAMANIAN, Ramkumar; BENADE, Vijay Sidram; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (89 pag.)WO2017/42643; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 127107-23-7,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.

General procedure: To 8a (0.25 g, 0.95 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloridesalt (0.14 g, 1.1 mmol) in n-butanol (5 mL) was added trifluoroaceticacid (0.27 g, 2.4 mmol), and the mixture was stirredovernight at 120 C. The mixture was then concentrated, neutralizedwith ammonia in methanol, and purified by column chromatography(dichloromethane: methanol=60:1) to yield 0.26 g (86.7%) of 9a as apale-yellow solid. MS (ESI) m/z 326 [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 1-Methyl-1H-pyrazol-4-amine hydrochloride, its application will become more common.

Reference:
Article; Yu, Ru-Nan; Chen, Cheng-Juan; Shu, Lei; Yin, Yuan; Wang, Zhi-Jian; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1646 – 1657;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 400755-44-4, name is 1-Ethylpyrazole-3-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. Safety of 1-Ethylpyrazole-3-carboxylic Acid

A mixture of 5-(3,5-difluorobenzyl)pyridin-2-amine (0.100 g, 0.45 mmol), 1 -ethyl- 7/-/-pyrazole-3-carboxylic acid (0.053 g, 0.38 mmol), 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (0.1 73 g, 0.45 mmol) and A/,A/-diisopropylethylamine (0.147 g, 1 .14 mmol) in anhydrous A/,A/-dimethylformamide (4.00 mL) was stirred at 20 C for 2 h. The reaction solution was extracted with ethyl acetate (20 ml_ x 20). The combined organic layers were washed with water (50 mL) and brine (50 mL) were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified via prep-HPLC (Boston C1 8 21 *250 mm 10 pm column; acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3,5-difluorobenzyl)pyridin-2-yl)-1 -ethyl- 7/-/-pyrazole-3-carboxamide (0.0304 g, 0.09 mmol, 23%) as a white solid. 1 H NMR (400 MHz, Dimethylsulfoxide-c/6) d 9.68 (s, 1 H), 8.32 (d, J = 1 .8 Hz, 1 H), 8.10 (d, J = 8.5 Hz, 1 H), 7.94 (s, 1 H), 7.79 (dd, J = 8.5, 2.2 Hz, 1 H), 7.13 – 6.95 (m, 3H), 6.85 (d, J = 2.3 Hz, 1 H), 4.26 (q, J = 7.3 Hz, 2H), 3.98 (s, 2H), 1 .44 (t, J = 7.3 Hz, 3H); LCMS (ESI) m/z: 343.1 [M+H]+.

The synthetic route of 1-Ethylpyrazole-3-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics