Tag: M.W:100-200

Application of 38858-90-1, The chemical industry reduces the impact on the environment during synthesis 38858-90-1, name is 4-Methyl-3-nitro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A solution of 4-methyl-3-nitro-1H-pyrazole (500 mg, 3.93 mmol), iodomethane (837.9 mg, 5.9 mmol) and potassium tert-butoxide (484.6 mg, 4.33 mmol) in tetrahydrofuran (20 mL) was stirred at 25 C. for 1 hour. The solvent was concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with dichloromethane/methanol (10/1) to afford 1,4-dimethyl-3-nitro-pyrazole (450 mg, 3.18 mmol) as a white solid. LCMS (ESI) [M+H]+=142

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

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 137890-05-2, name is 1-(1-Methyl-1H-pyrazol-5-yl)ethanone, 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 137890-05-2, COA of Formula: C6H8N2O

Under N2, a mixture of intermediate 1 lb (1 g) and 5-acetyl-l-methylpyrazole (168mgl.35 mmol) in THF (15 mL) was stirred at rt overnight. Then, NaBH(OAc)3 (718 mg;3.4 mmol) was added portion wise. The reaction mixture was stirred at room temperature for 72h, poured into cold water, basified with K2C03 powder and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH, 12g; mobile phase:gradient from 100% DCM, 0% MeOH to 95% DCM, 5% MeOH, 0.3% NH4OH). The fractions were collected and evaporated to dryness. The residue (300 mg) was purified asecond time by reverse phase chromatography (YMC-actus Triart Cl 8 1 Ojim30*150mm; mobile phase: gradient from 65% NH4HCO3 0.2% aq, 35% ACN to 25%NH4HCO3 0.2% aq, 75% ACN). The pure fractions were collected, evaporated to drynessyielding 104 mg of compound 224.

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; 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

Synthetic Route of 2654-57-1, These common heterocyclic compound, 2654-57-1, name is 4-Methyl-1-phenylpyrazolidin-3-one, 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-Methyl-1-phenyl-1,2-dihydro-3H-pyrazol-3-one (5) was synthesized in a similar way from 0.17 g (1 mmol) of 4-methyl-1-phenylpyrazolidin-3-one (3) in 1 mL of methylene chloride and 0.19 g (1.01 mmol) of 1 in 1 mL of methylene chloride at room temperature. Yield 0.15 g (88%), yellow powder, mp 209 C [5, 6]. 1H NMR spectrum, delta, ppm: 1.90 s (3H, CH3), 7.12 t (1H, p-H, J = 7.3 Hz), 7.38 t (2H, m-H, J =8.1 Hz), 7.60 d (2H, o-H, J = 7.8 Hz), 8.01 s (1H,=CH), 10.14 (1H, NH). 13C NMR spectrum, deltaC, ppm:7.0, 103.3, 116.2, 123.9, 126.5, 129.3, 139.9, 161.4. The spectral parameters of 5 coincided with those given in [5, 6].

The synthetic route of 2654-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shainyan; Tolstikova; Russian Journal of Organic Chemistry; vol. 53; 4; (2017); p. 632 – 633; Zh. Org. Khim.; vol. 53; 4; (2017); p. 624 – 625,2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1001020-13-8,Some common heterocyclic compound, 1001020-13-8, name is (3-Trifluoromethyl-1H-pyrazol-4-yl)methanol, molecular formula is C5H5F3N2O, 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.

(S)-benzyl-5-(hydiOxymethyl)-2,3-dihydro-7 /-/-inden-2-ylcarbamate (7.13 mmol, 2.12g) was dissolved in DCM (20 ml_), thionyl chloride (14.26 mmol, 1.040 ml_, 1.696 g) added and the resultant solution stirred at room temperature for 45 min. The sample was concentrated and azeotroped with dichloromethane (x 4). Potassium carbonate (21.39 mmol, 2.96 g) was added followed by DMF (20 ml.) and (3-(trifluoromethyl)-1 H-pyrazol-4- yl)methanol (7.13 mmol, 1.184 g) and the mixture heated to 60 0C for 1 h. The mixture was concentrated and partitioned between ethylacetate/water. The aqueous layer was twice extracted with ethylacetate and combined organics dried, filtered and concentrated to give a yellow oil which was purified on silica eluting with 0 – 1 % MeOH/DCM to give (S)-benzyl-5-((4-(hydroxymethyl)-3-(trifluoromethyl)-7/-/-pyrazol-1-yl)methyl)-2,3-dihydro- 7H-inden-2-ylcarbamate as a light coloured oil (2.67 g, 84 %). 1H NMR (400 MHz, CDCI3) delta 1.83 (t, 1 H) 2.79 (m, 2H) 3.27 (m, 2H) 4.51 (bs, 1 H) 4.63 (d, 2H) 4.98 (bs, 1 H) 5.08 (bs, 2h) 5.24 (s, 2H) 7.05-7.1 1 (m, 2H) 7.18 (m, 1 H) 7.26-7.39 (m, 6H).

The synthetic route of 1001020-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 90253-21-7, name is 4-Cyclopropyl-1H-pyrazole, 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 90253-21-7, HPLC of Formula: C6H8N2

To a 20 ml vial, compound 211 I-135 (25.0 mg, 0.084 mmol) and 195 copper iodide (1.607 mg, 8.44 mumol) were added followed by 213 4-cyclopropyl-1H-pyrazole (9.13 mg, 0.084 mmol) and 196 trans-N,N?-dimethylcyclohexane-1,2-diamine (2.401 mg, 0.017 mmol). This mixture was then evacuated and backfilled with nitrogen (3 times). Then dry, degassed 214 1,2-dioxane (338 mul) was added. The mixture was heated at 110 C. for 24 h and cooled to RT. The crude material was purified by mass-directed reversed phase chromatography (ACN/water gradient with 0.1% 19 TFA modifier) to afford the 215 title compound. MS (ESI) [M+H]+: m/z 324. 1H NMR (600 MHz, DMSO-d6) delta 8.22 (s, 1H), 7.70 (d, J=8.4 Hz, 2H), 7.59 (q, J=6.1, 5.5 Hz, 1H), 7.51 (d, J=18.9 Hz, 1H), 7.39 (d, J=8.4 Hz, 2H), 2.96 (p, J=7.0 Hz, 2H), 2.77-2.62 (m, 2H), 2.33 (dq, J=19.2, 10.1, 9.3 Hz, 2H), 1.86-1.68 (m, 3H), 1.32 (p, J=7.1 Hz, 2H), 0.86 (t, J=6.2 Hz, 2H), 0.70 (t, J=7.3 Hz, 3H), 0.58 (d, J=4.0 Hz, 2H).

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

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 436096-96-7, 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 436096-96-7 as follows.

Preparation 68: [3′-(4-Fluorophenyl)-2,3,5,6-tetrahydro-[l,2′]bipyrazinyl-4-yl]-(l- isopropyl-lH-pyrazol-4-yl)-methanone Dissolve l-isopropyl-lH-pyrazole-4-carboxylic acid (0.120 g, 0.780 mmol) inDCM (5 mL). Add etaOBt (0.088 g, 0.650 mmol) followed by l-(3-dimethyl- aminopropyl)-3-ethylcarbodiimide hydrochloride (0.125 g, 0.650 mmol). Add 3′-(4- fluorophenyl)-3,4,5,6-tetrahydro-2eta-[l,2′]bipyrazinyl (0.168 g, 0.650 mmol) and stir at room temperature for 18 hr. Add DCM and water and separate layers. Extract aqueous layer 3 times with DCM, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 25:75 to 100:0 ethylacetate/hexanes), to give the title preparation (211 mg, 82%). MS (ES): m/z = 395 [M+H]+.

According to the analysis of related databases, 436096-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1904-24-1,Some common heterocyclic compound, 1904-24-1, name is 3-Amino-5-ethylpyrazole, 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.

Method 79; 6-Ethyl-2-chloro-4- (5-ethyl-lH-pvrazol-3-ylamino) pyrimidine 2,4-Dichloro-6-ethyl-pyrimidine (J. Am. Chem. Soc. 1936, 58, 78) (1.33g 7.53mmol) was stirred in ethanol (50ml) and 5-ethyl-lH-3-amino-pyrazole (Method 6 of WO 03/048133) (0. 836g, 7.53mmol) was added followed by sodium carbonate (1.25g) and the mixture stirred at 40C for 4 days then at 55C overnight. The insoluble inorganics were removed by filtration and solvent removed from the filtrate by evaporation. Water (100ml) was added and the mixture extracted with EtOAc (3 x 50ml). The extracts were combined and washed with water (50ml), brine (50ml), dried (MgS04) and solvent removed by evaporation. The residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (100: 0 increasing in polarity to 0: 100) to give the title compound (210mg, 11%) a white solid. NMR (DMSO-d6 at 100C) : 1.20 (m, 6H), 2.50-2. 70 (m, 4H), 6.05 (s, 1H), 7.05 (br s, 1H), 9.70 (br s, 1H), 11.85 (br s, 1H) ; m/z 252 [MH] +.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/40159; (2005); 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. 2654-57-1, name is 4-Methyl-1-phenylpyrazolidin-3-one, A new synthetic method of this compound is introduced below., Quality Control of 4-Methyl-1-phenylpyrazolidin-3-one

General procedure: 1a (0.5?mmol), Pd(OAc)2 (5?mol%), AMS (20?mol%), K2CO3 (0.4 equiv.), and dry chlorobenzene (1?mL) were added in a test tube. The reaction mixture was allowed to stir vigorously at 110?C for 6?h. After cooling at room temperature, the mixture was concentrated and the residue was purified by column chromatography on Al2O3 (mobile phase: dichloromethane/methanol or petroleum ether/ethyl acetate) to afford the pure product.

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; Zhu, Ye-Fu; Wei, Bo-Le; Wei, Jiao-Jiao; Wang, Wen-Qiong; Song, Wei-Bin; Xuan, Li-Jiang; Tetrahedron Letters; vol. 60; 17; (2019); p. 1202 – 1205;,
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. 3273-44-7, name is 5-Methyl-1H-pyrazole-3-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Methyl-1H-pyrazole-3-carbaldehyde

General procedure: To a suspension of 5-methyl-1H-pyrazole-3-carbaldehyde (18; 2-6 equiv) in anhydrous THF (10 mL) (in the case of the synthesis of 1) or MeOH (in the case of the synthesis of 2-5 and 11), the corresponding derivative bearing one to three amino groups (17,21 25-289d,11 or 36,4c see Scheme 1 and Scheme 2) (1 equiv), dissolved in anhydrous MeOH (5 mL), was added. The resulting mixture was heated at reflux until a clear solution resulted and then stirred at r.t. (up to 4 days, TLC analysis). The resulting imines were reduced without further purification by addition of NaBH4 (3-9 equiv) in portions. After complete addition of the reducing agent, the reaction mixture was stirred for 24 h at r.t. and then the solvent was removed under reduced pressure. The residue was suspended in CHCl3-H2O (1:1, 10 mL) and stirred for 12 h at r.t. The resulting suspension was extracted with CHCl3 (3 × 20 mL), dried over MgSO4, and the solvent was removed. The crude product was purified by column chromatography.

According to the analysis of related databases, 3273-44-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koch, Niklas; Seichter, Wilhelm; Mazik, Monika; Synthesis; vol. 48; 17; (2016); p. 2757 – 2767;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 25700-12-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 25700-12-3 name is 3-(1H-Pyrazol-1-yl)pyridine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a mixture of 3-(1H-pyrazol-1-yl)pyridine (5 g, 34.4 mmol), iodic acid (1.212 g, 6.89 mmol), and iodine (3.50 g, 13.78 mmol) in acetic acid (49.2 ml) was added sulfuric acid (0.918 ml, 17.22 mmol). The reaction mixture heated to 70 C. for 30 min. The reaction mixture was poured onto ice water, extracted with Et2O and then was washed with sodium thiosulfate solution. The organics were then dried with MgSO4, filtered and concentrated in vacuo. The residue purified by flash chromatography eluting with 0-50% acetone in dichloromethane to yielded a light tan solid (6.1 g, 21.38 mmol, 62.1% yield): mp 145-146 C.; 1H NMR (400 MHz, acetone-d6) delta 9.11 (d, J=2.3 Hz, 1H), 8.60 (d, J=0.5 Hz, 1H), 8.56 (dd, J=4.7, 1.4 Hz, 1H), 8.22 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.84 (s, 1H), 7.54 (ddd, J=8.3, 4.7, 0.7 Hz, 1H); EIMS m/z 271.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(1H-Pyrazol-1-yl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics