Tag: M.W:200-300

Synthetic Route of 595610-50-7, 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. 595610-50-7, name is 5-(3-Chlorophenyl)-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To amixture of 3-(3-chlorophenyl)-1H-pyrazole-5-carboxylic acid (14a, 133 mg, 0.60 mmol) inDMF(4 mL)was added (S)-methyl-4-(2-amino-3-phenylpropanamido)benzoate hydrochloride (12, 200 mg,0.60 mmol), N,N-diisopropyl-ethylamine (232 mg, 1.80 mmol), 1-hydroxybenzotriazole(161 mg,1.20 mmol) and N-(3-dimethylaminopropyl)-N0-ethylcarbodiimide hydrochloride (229 mg, 1.20 mmol)and the reaction mixture was stirred at room temperature overnight.Then TLC analysis indicatedreaction was complete, and H2O (40 mL) was added.The mixture was stirred for 10 min and filtered toget crude product 13a as a yellow solid, which was used for next step without further purification.

The synthetic route of 5-(3-Chlorophenyl)-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Qunchao; Zheng, Zhichao; Zhang, Shijun; Zheng, Xuemin; Meng, Fancui; Yuan, Jing; Xu, Yongnan; Huang, Changjiang; Molecules; vol. 23; 8; (2018);,
Pyrazole – Wikipedia,
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Application of 199678-06-3,Some common heterocyclic compound, 199678-06-3, name is 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, molecular formula is C11H10N2O2, 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 4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (3.5 g, 17.3 mmol) in DCM (100 mL) was added N,O-dimethylhydroxylamine hydrochloride (2.0 g, 20.8 mmol),(dimethylamino)-N,N-dimethyl(3H- [1,2,3 ]triazolo[4, 5 -b]pyridin-3 -yloxy)-methaniminium hexafluorophosphate (7.9 g, 20.8 mmol) and N,N-diisopropylethylamine (8.58 mL, 51.9 mmol). The mixture was stirred at room temperature for 8 h. The reaction mixture was washed with 1 N HC1 (100 mL x 2), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 3 : 1) to give thetitle compound (3.2 g, 75%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 754219-01-7, name is Ethyl 5-iodo-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H9IN2O2, 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. category: pyrazoles-derivatives

A mixture of ethyl 5-iodo-1-methyl-pyrazole-4-carboxylate (7.5 g, 26.8 mmol) and lithium hydroxide (6.4 g, 268.0 mmol) in tetrahydrofuran (100 mL) and water (100 mL) was stirred at 25 C. for 15 h and concentrated under reduced pressure. The residue was adjusted to pH=5 by additional of hydrochloric acid (2 N). The formed solid was collected by filtration, washed with water (20 mL) and dried in vacuo to afford crude 5-iodo-1-methyl-1H-pyrazole-4-carboxylic acid (6.0 g, 89%) as a white solid, used as is in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 754219-01-7, its application will become more common.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); 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. 1269293-48-2, name is Ethyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1269293-48-2

STEP A: 5-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid [0180] Lithium hydroxide (8.58 mL, 17.16 mmol) was added to a mixture of ethyl 5- bromo-1 -methyl- lH-pyrazole-3-carboxylate (1 g, 4.29 mmol) in THF (10 mL) and water (2 mL). The reaction mixture was stirred for 5 hours at room temperature and was subsequently concentrated, acidified with concentrated HC1, and extracted into EtOAc. The organic layer was dried over Na2S04 and concentrated to give the title compound as a white solid (0.72 g, 82%).

The synthetic route of 1269293-48-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; TANG, Mingnam; WO2014/39831; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 59074-26-9,Some common heterocyclic compound, 59074-26-9, name is 3-(4-Chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole, molecular formula is C15H13ClN2, 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 A: A stirred solution of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (5.00 gram, 19.5 mmol) and N-(tert-butoxycarbonyl)aziridine (2.00 gram, 14.0 mmol) in toluene (100 ml) was heated at reflux temperature for 16 hours. After concentration in vacuo the residue was purified by flash chromatography (petroleum ether/diethyl ether=3/1 (v/v)), followed by petroleum ether/diethyl ether=1/1 (v/v)). After concentration in vacuo the remaining oily residue was crystallized from diisopropyl ether to afford 1-[2-((tert-butoxycarbonyl)amino)ethyl]-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (1.91 gram, 34%). Repeated crystallisations from the mother liquor afforded an additional amount of crystalline 1-[2-((tert-butoxycarbonyl)amino)ethyl]-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (1.19 gram).

The synthetic route of 59074-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Solvay Pharmaceuticals B.V.; US2001/53788; (2001); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1239363-40-6,Some common heterocyclic compound, 1239363-40-6, name is 1-Cyclopropyl-4-iodo-1H-pyrazole, molecular formula is C6H7IN2, 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 potassium phosphate tribasic (792 mg, 3.73 mmol) and l-cyclopropyl-4-iodo-lH- pyrazole (437 mg, 1.866 mmol) in DMSO (10 mL) were added intermediate 41.4 (530 mg, 1.244 mmol), Irans-N 1.N2-dimethylcycloheane- 1.2-diamine (35.4 mg, 0.249 mmol) and copper(I) iodide (237 mg, 1.244 mmol) at room temperature. The mixture was stirred for 36 h at 90C under N2 atmosphere. 16% NEL aqueous (20 mL) was added to the mixture and this mixture was extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (20 mL), dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to give intermediate 41.5, 6-(l-(4-(benzyloxy)-3-methyltetrahydrofuran-3-yl)piperidin-4-yl)-5-chloro-l-(l-cyclopropyl- lH-pyrazol-4-yl)-lH-indazole. MS (ESI) m/z calc?d for C30H35CIN5O2 [M+H] + 532 found 532.

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-4-iodo-1H-pyrazole, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 199678-06-3, name is 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, 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 199678-06-3, name: 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid

EXAMPLE 55 [4-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepin-10-yl)-methanone oxalyl chloride (0.30 g) was added to a suspension of 4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid (0.46 g) in dichloromethane (25 ml).. Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature.. The resultant solution was evaporated to dryness to yield the crude acid chloride (0.57 g), which was utilized without further purification. The acid chloride was added to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine (0.37 g) and diisopropylethylamine (0.58 g) in dichloromethane (50 ml).. After 18 hours at room temperature, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate.. The dichloromethane solution was dried over anhydrous sodium sulfate and littered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane.. The combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred.. After cooling, the crystals were collected by filtration to yield the tide compound (0.38 g), m.p. 200-201 C; MS m/z: 368 (M)+.

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Reference:
Patent; Wyeth; EP1000062; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 75092-30-7, name is 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H5IN2O2, 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. Formula: C5H5IN2O2

Step 1. 1-Methyl-4-[(4-methylphenyl)amino]-1H-pyrazole-5-carboxylic acid A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Y. A. Manaev et al., J. Gen. Chem. USSR. (Engl. Transl.), 1982, 52, 2291), 2.92 g, 11.6 mmol), p-toluidine (6.20 g, 57.9 mmol), and copper powder (1.17 g, 18.4 mmol) in 5% aqueous sodium carbonate (60 ml) was stirring at 100 C. for 5 h. After cooling to room temperature, diethyl ether (100 ml) and 2N aqueous sodium hydroxide (100 ml) were added. This mixture was filtered through a pad of Celite, which was washed with 2N sodium hydroxide (200 ml) and ether (100 ml). The separated aqueous layer was washed with ether (100 ml), filtered through a pad of Celite again, and acidified with concentrated hydrochloric acid. The precipitate was collected by filtration, and washed with water to give 1.77 g (76.6 mmol, 66%) of the title compound as a gray powder. MS (EI) m/z: 231 (M+). 1H-NMR (DMSO-d6) delta: 7.61 (1 H, s), 7.05 (2 H, d, J=8.6 Hz), 6.98 (2 H, d, J=8.9 Hz), 4.00 (3 H, s), 2.22 (3 H, s). Two signals due to NH and CO2H were not observed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 75092-30-7, its application will become more common.

Reference:
Patent; Kawamura, Kiyoshi; Mihara, Sachiko; Nukui, Seiji; Uchida, Chikara; US2003/130277; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 51516-68-8, name is 5-Amino-1-(3-chlorophenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C10H7ClN4, 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. name: 5-Amino-1-(3-chlorophenyl)-1H-pyrazole-4-carbonitrile

General procedure: 5-amino-1-aryl-1H-pyrazole-4-carbonitriles 4(aei) (0.001 mol),2.0 mL of 1,2-diaminoethane (ethylenediamine) and carbon disulfide(0.004 mol) were added into a 50 mL round-bottom flaskadapted with a glass condenser. The mixture was kept at 110-115oCfor 12-14 hours. After that, the productwas poured into cold water,the precipitate was filtered out and washed with cold water. Thereactions were accompanied by means of TLC and dichloromethaneas eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51516-68-8, its application will become more common.

Reference:
Article; Monteiro; Lechuga; Lara; Souto; Vigano; Bourguignon; Calvet; Oliveira; Alves; Souza-Silva; Santos; Pereira; European Journal of Medicinal Chemistry; vol. 182; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 93608-11-8, 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. 93608-11-8, name is 3-Bromo-5-(trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3-Bromo-l-(4-nitrophenyl)-5-(trifluoromethyl)-l /-pyrazole 23b: To a stirred suspension of 22b (5.0 g, 23.3 mmol, 1.0 equiv) and anhydrous potassium carbonate (3.9 g, 27.9 mmol, 1.2 equiv) in DMF (116 mL), l-fluoro-4-nitrobenzene (2.5 mL, 23.5 mmol, 1.01 equiv) was added at 25 C, and the reaction mixture was heated to 80 C for 12 h. After cooling to 25 C, the reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (20 mL), and the two phases were separated. The aqueous layer was extracted with ethyl acetate (3 chi 15 mL), and the combined organic layers were backwashed with water (2 chi 15 mL) and brine (15 mL), dried with anhydrous magnesium sulfate, and concentrated in vacuo. Flash column chromatography (silica gel, 8% to 20% ethyl acetate in hexanes) with a slow gradient to separate the undesired regioisomer afforded 23b (1.57 g, 4.66 mmol, 20%) as a white amorphous solid. 23b: Ri = 0.61 (silica gel, 20% ethyl acetate in hexanes); FT-IR (neat) V 3149, 2923, 2853, 1598, 1527, 1502, 1454, 1347, 1288, 1216, 1180, 1141, 1112, 1076, 986, 963, 854, 812, 757, 689 cm 1; NMR (600 MHz, CDC13) delta = 8.37 (d, J = 9.0 Hz, 2 H), 7.71 (d, J = 9.0 Hz, 2 H), 6.93 (s, 1 H) ppm; 13C NMR (151 MHz, CDC13) 5 = 148.1, 143.1, 134.3 (q, J = 40.4 Hz), 128.6, 125.9, 124.9, 116.1 (q, J= 270.0 Hz), 113.3 (q, J= 2.6 Hz) ppm; HRMS (ESI) calcd for Ci0H5BrF3N3O2 [M+H]+ 335.9590 found 335.9588.

The synthetic route of 3-Bromo-5-(trifluoromethyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WILLIAM MARSH RICE UNIVERSITY; NICOLAOU, Kyriacos, C.; RHOADES, Derek; WANG, Yanping; TOTOKOTSOPOULOS, Sotirios; (191 pag.)WO2017/66606; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics