Tag: M.W:100-200

Related Products of 5744-40-1, A common heterocyclic compound, 5744-40-1, name is Ethyl 1,3-dimethyl-1H-pyrazole-5-carboxylate, molecular formula is C8H12N2O2, 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.

Lithium aluminum hydride(l.OM in tetrahydrofuran, 1.78 mL) solution was added to commercially available ethyl 1,3-dimethyl-l//-pyrazole-5-carboxylate (Jl, 300 mg, 1.78 mmol) in tetrahydrofuran over 5 minat room temperature. The reaction stirred overnight. In succession water (67 |j,L), 15%aqueous sodium hydroxide (202 uL), water (67 |aL) were added. The resulting solid wasfiltered and dried in vacua, then purified by chromatography (3% to 7% methanol indichloromethane) to yield 175 mg of a colorless solid, J2.

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; AMGEN INC.; WO2006/4915; (2006); 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. 25252-46-4, name is 1,3-Dimethyl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 25252-46-4

N-methoxy-N,1,3-trimethyl-1H-thieno[2,3-c]pyrazole-5-carboxamide A solution of 1,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (2 g, 10.19 mmol, 1.00 equiv) methoxy(methyl)amine hydrochloride (1.06 g, 10.87 mmol, 1.10 equiv), DIEA (4 g, 30.95 mmol, 3.00 equiv), and HATU (5.8 g, 15.26 mmol, 1.50 equiv) in DMF (30 mL) was stirred for 2 h at rt, diluted with 100 mL of water, and extracted with 2×100 mL of EtOAc. The combined organic layers were washed with 100 mL brine, dried over Na2SO4, concentrated under vacuum, and purified with silica gel chromatography using EtOAc/petroleum ether (1:3) to afford 2.2 g (90%) of the title compound as a yellow solid. LC-MS: (ES, m/z): 240

According to the analysis of related databases, 25252-46-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vettore, LLC; PARNELL, Kenneth Mark; MCCALL, John; ROMERO, Donna; (172 pag.)US2018/162822; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 138786-86-4, These common heterocyclic compound, 138786-86-4, name is Methyl 4-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.

PART I: Synthesis Scheme I, shows that 4-nitro-1H-pyrazole-3-carboxylic acid (compound 12) was alkylated with methyl iodide in the presence of potassium carbonate in DMF. After flash chromatography on silica gel, two regioisomers, alkyl 1-alkyl-4-nitro-1H-pyrazole-3-carboxylate (compound 13a, 1,3-isomer) and alkyl 1-alkyl-4-nitro-1H-pyrazole-5-carboxylate (compound 13b, 1,5-isomer) were obtained in 26% and 74% yield, respectively. The structures of the isomers (compounds 13a, 13b) were determined by NOESY analysis: a NOESY correlation was observed between H-5 and alkyl protons in compound 13a.16 The nitro group of compounds 13a and 13b was reduced by hydrogenation in the presence of a catalytic amount of catalytic amount of 10% Pd/C to produce amines compounds 14a and 14b, respectively. Cyclization of compound 14b with urea afforded compound 15. Chlorination of compound 15 with POCl3 and DIPEA in toluene afforded compound 16 in 68% yield. Treatment with appropriate substituted anilines in isopropanol with 1 drop of conc. HCl with compound 16, provided the instant compounds 4-11 of this invention (65-78% yields).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duquesne University of the Holy Spirit; Gangjee, Aleem; (26 pag.)US2019/276457; (2019); 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. 15754-60-6, name is 1-(tert-Butyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(tert-Butyl)-1H-pyrazole

0481-1 Iodine (1.59 g) and ammonium cerium nitrate (3.45 g) were added to a solution of 1-(tert-butyl)-1H-pyrazole (1.30 g) in acetonitrile (6 mL), followed by stirring at room temperature for 2 hours. After ethyl acetate and water were added to the reaction mixture, the organic layer was collected by separation, washed sequentially with a 10% sodium hydrogen sulfite aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 1-(tert-butyl)-4-iodo-1H-pyrazole (487 mg). MS m/z (M+H): 251.

The synthetic route of 15754-60-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 64517-88-0, name is 1,3-Dimethyl-1H-pyrazol-4-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. Quality Control of 1,3-Dimethyl-1H-pyrazol-4-amine

Example 4.28 7- [ [2- [(1 ,3-Dimethylpyrazol-4-yl)aminol -5-fluor o-4-pyridvH aminol -4-(4- isopropylpiperazin-l-yl)-2-methyl-isoindolin-l-one A mixture of 7-[(2-chloro-5-fluoropyridin-4-yl)amino]-2-methyl-4-(4-propan-2- ylpiperazin-l-yl)-3H-isoindol-l-one (150 mg, 0.36 mmol), l,3-dimethylpyrazol-4-amine (80 mg, 0.72 mmol), cesium carbonate (234 mg, 0.72 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (24.92 mg, 0.04 mmol) and palladium(II) acetate (6.45 mg, 0.03 mmol) was suspended in DMA (2 mL) under an atmosphere of nitrogen. The mixture was heated at 1500C for 60 minutes in a microwave reactor and then allowed to cool to room temperature. The mixture was filtered and the filtrate evaporated. The residue was dissolved in MeOH (20 mL) and the solution made acidic (pH6) by the addition of 2M HCl. The mixture was loaded onto an SCX column and the product eluted first wit MeOH and then with a 0.7M solution OfNH3 in MeOH. Fractions containing product were combined and evaporated and the residue was then purified by preparative HPLC. Fractions containing product were combined and evaporated to afford example 4.28 (45.4 mg, 26% yield); 1H NMR spectrum (300 MHz, DMSO): delta 1.02 (6H, d), 2.11 (3H, s), 2.60 (4H, t), 2.70 (IH, m), 2.99 (4H,m), 3.06 (3H, s), 3.70 (3H, s), 4.48 (2H, s), 6.92 (IH, d), 7.15 (IH, d), 7.39 (IH, d), 7.86 – 7.93 (3H, m), 9.26 (IH, d); Mass spectrum: m/z (ESI+) (M+H)+ = 493.44.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64517-88-0, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/153589; (2009); 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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H7N3O4

B) Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate To a solution of methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate (10 g) in methanol (200 mL), palladium-carbon (10%) (2 g) was added, and the mixture was stirred at room temperature for 6 hours in a hydrogen atmosphere (45 psi). Palladium-carbon was filtered off, and then, the filtrate was concentrated to obtain the title compound (8.57 g). 1H NMR (400 MHz, CDCl3) delta 3.86 (3H, s), 3.92 (3H, s), 4.08 (2H, brs), 6.96 (1H, s).

The synthetic route of 400877-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; ASANO, Yasutomi; KOJIMA, Takuto; KURASAWA, Osamu; WONG, Tzu-Tshin; HIRATA, Yasuhiro; IWAMURA, Naoki; SAITO, Bunnai; TANAKA, Yuta; ARAI Ryosuke; IMAMURA, Shinichi; YONEMORI, Kazuko; MIYAMOTO, Yasufumi; KITAMURA, Shuji; SANO, Osamu; (222 pag.)EP3287441; (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. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C5H7N3O2

To an ice cold suspension of 0.92 g (23 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) (previously washed with hexane and dried under vacuum) in 25 mL of 1,2- dimethoxyethane (DME) was added 0.9 g (5.76 mmol) of [METHYL CYCLOHEXYLACETATE,] and the resulting mixture was stirred at [0 C] for 20 min. Then 1.2 g (8.56 mmol) [OF ETHYL 2-FUROATE] was added, and the reaction mixture was heated at reflux overnight. The mixture was then cooled to [0C,] quenched by the addition of 1 M [HC1] solution to pH=3, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to give a brown oil which was chromatographed on silica gel [(BIOTAGE ;] 10% hexane in dichloromethane) to afford 1.1 g (76% yield) of desired 2-cyclohexyl-3-furan-2-yl-3- [OXO-PROPIONIC ACID METHYL ESTER] as indicated by 1H NMR. A mixture of 1.1 g (4.4 mmol) [OF 2-CYCLOHEXYL-3-FURAN-2-YL-3-OXO-P7 OPIONIC ACID] [METHYL ESTER,] 0.592 g (4.2 mmol) of 5-amino-1H-pyrazole-3-carboxylic acid methyl ester, 76 mg (0.4 mmol, 10 mol%) of p-toluenesulfonic acid monohydrate (PTSA), and 50 mL of chlorobenzene was heated at 120 [C] overnight. The reaction mixture was then concentrated to a residue which was chromatographed on silica gel (7% methanol in dichloromethane) to afford 0.46 g (32% yield) of desired 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro- pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester as indicated [BY IH] NMR; LC-MS- calcd for [C18HL9N304] [[M++H] +] : 342.14, found: 342.3. Conversion of 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine- 2-carboxylic acid methyl ester to 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro-pyrazolo[1,5- [AJPYYIMIDINE-2-CARBOXYLIC ACID] (595) was accomplished via the well known LiOH saponification protocol where the yield was 77%. [LC-MS-CALCD] for [CI7HI7N304] [M++H]+: 328.13, found : 328. 1. 1H NMR [(DMSO-D6)] [8] 8.06-8. 05 (d, J= 2 Hz, 1H), 6.99-6. 98 (d, J= 3.6 Hz, 1H), 6.80-6. 78 (d [OF D,] J= 3.6 Hz, J= 2 Hz, [1H),] 6.39 (s, [1H),] 2.79-2. 71 [(M,] 1H), 2.25-2. 16 [(M,] 2H), 1.77-1. 75 [(M,] [2H),] 1.66-1. 65 [(M,] 1H), 1.59-1. 55 [(M,] 2H), 1.25-1. 20 [(M,] 3H). Note that the same synthetic scheme was carried out for [3-FLUORO-BENZOIC ACID METHYL] ester as depicted above to afford [6-CYCLOHEXYL-5-(3-FLUORO-PHENYL)-7-OXO-4, 7-DISLYDRO-] pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (598); the cyclization yield was slightly improved (54%).

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; NEOGENESIS PHARMACEUTICALS, INC.; WO2003/101993; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 52222-73-8, 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. 52222-73-8 name is 4-(Trifluoromethyl)-1H-pyrazole, 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.

[00564] Intermediate 57a: ethyl 2-[4-(trifluoromethyl)pyrazol-1 -yI]acetate [00565] 4-(Trifluoromethyl)-1 H-pyrazole (100mg, 0.73mmol) and potassium carbonate (305mg, 2.2Ommol) were left to stir in MeCN (2mL) for 30 minutes at room temperature before the addition of ethyl bromoacetate (0.l2mL, 1.lOmmol). The reaction mixture was then heated to 60C and left to stir at this temperature for 2 hours. The reaction was allowed to cool to room temperature andquenched by the addition of water (2OmL) and this solution was extracted with EtOAc (3 x 2OmL).The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to giveethyl 2-[4-(trifluoromethyl)pyrazol-1-yl]acetate (1 60mg, 0.72mmol, 100% yield) as a yellow oil.1H NMR (CDCI3,400MHZ) O/ppm: 7.82 (1H, 5), 7.77 (1H, 5), 4.95 (2H, 5), 4.29 (2H, q, J= 7.1Hz),1.32 (3H, t, J= 7.1Hz).MS Method 2: RT: 1.54 mi mlz 222.9 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethyl)-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25016-11-9, These common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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 solution of 1-(methylsulfonyl)-5,6-dihydropyridin-2(11])-one (200 mg, 1.14 mmol, 1.0 eq), diethyl phosphorochloridate (197 mg, 1.14 mmol, 1 eq) and 1-methyl-1H-pyrazole-4- carbaldehyde (100 mg, 0.91 mmol, 0.8 eq) in THF (10 mL) at 0C was added LiHIVIDS 1M in THF (2.5 mL, 2.50 mmol, 2.0 eq). The reaction mixture was stirred at 0C for lh. Progress ofreaction was monitored by TLC. Reaction mixture was quenched by saturated ammonium chloride solution 20 mL and extracted with ethyl acetate (3 x 50 mL). Combined organic layer was washed with brine solution (50 mL) and dried over anhydrous Na2SO4. Removal of solvent under reduced pressure gave the crude which was purified by flash column chromatograpy (0-70% EtOAc-hexane) as eluent to 1- { [(E)-2-( 1-methyl- 1H-pyrazol-4-yl)ethenyl] sulfonyl } -5,6-dihydropyridin-2(11])-one (90 mg, 29.50%).LCMS: 268[M+1]1H NMR (400IVIHz, CDC13) (57.69 (s, 1 H), 7.59 (s, 1 H), 7.55 (d, 1 H), 6.91 (d, 1 H), 6.81 -6.86 (m, 1H), 5.97 (d, 1 H), 3.96 (t, 2 H), 3.92 (s, 3 H), 2.51 – 2.57 (m, 2 H),

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1151814-36-6,Some common heterocyclic compound, 1151814-36-6, name is 1-Cyclopropyl-1H-pyrazole, molecular formula is C6H8N2, 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 1 1-cyclopropyl-4-iodo -1H- pyrazole-pyrazole 100 mg, cyclopropyl boronic acid 253 mg, sodium carbonate 312 mg 1,2-dichloroethane in addition to 2.5 ml, was added dropwise 1,2-dichloroethane 5ml with copper acetate 267mg and 2,2-bipyridine 230mg was suspended and stirred for 4 hours at 70 C..After dilution with ethyl acetate, saturated aqueous ammonium chloride solution, washed successively with water and saturated brine, and dried over magnesium sulfate.Under reduced pressure, after the evaporation of the solvent gave 148mg as a yellow oil.

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

Reference:
Patent; NIPPON SHINYAKU COMPANY LIMITED; FUJIHARA, HIDETAKA; ASAKI, TETSUO; HORI, KATSUTOSHI; NAITO, HARUNA; (146 pag.)JP5668756; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics