Category: 96450-53-2

Electric Literature of 96450-53-2,Some common heterocyclic compound, 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole, molecular formula is C5H7ClN2, 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 methyl 2,6-dioxo-l,2,3,6-tetrahydropyrimidine-4-carboxylate (900 mg, 5.29 mmol) was added DMF (17 mL). The mixture was cooled with an ice bath and lithium hydride (66.4 mg, 7.94 mmol) was then added in portions. The mixture was stirred for 20 minutes and ((chloromethoxy)methyl)benzene (0.899 mL, 5.82 mmol) in DMF (3 mL) was then added slowly via syringe. The mixture was stirred a 00C for 30 minutes. Lithium hydride (66.4 mg, 7.94 mmol) was then added in portions and stirred for 10 minutes. Sodium iodide (793 mg, 5.29 mmol) and l-(2-chloroethyl)-l/f-pyrazole (829 mg, 6.35 mmol) were added in portions and then stirred at 00C for 30 minutes. The ice bath was removed. The mixture was stirred at room temperature for 4 hours and then heated to 500C with stirring for 3 days. The reaction mixture was cooled to room temperature. Water (25 mL) and methanol (25 mL) were added and the solvents were evaporated under vacuum at 65C to give a residue, which was partitioned between IN NaOH (75 mL) and diethyl ether (50 mL). The organic layer was separated and the aqueous layer was washed with diethyl ether (2 x 50 mL). The aqueous layer was then acidified to pH=3 with IN HCl and then extracted with n-BuOH (5 x 100 mL). The organic layers from the n-BuOH extraction were combined and the solvent was evaporated under vacuum to give a residue which was purified by HPLC (40% ACN in water containing 0.05% TFA) to give the title compound. MS [M+H] found 371.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Chloroethyl)-1H-pyrazole, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FENG, Jun; KEUNG, Walter; LARDY, Matthew; WO2010/129848; (2010); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 96450-53-2, 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. 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

As shown in step 20-i of Scheme 20, 2-(5,6-dimethoxypyridin-3-yl)-6-(lH- pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-¾]pyridin-5-one [Compound 70, 100 mg, 0.2964 mmol, prepared from 2-chloro-6-(lH-pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-¾]pyridin-5- one and 2,3-dimethoxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (Compound 2021) in a manner similar to the preparation of compound 135 as shown in Example 12], and cesium carbonate (193 mg, 0.593 mmol), were weighed into a conical microwave vial equipped with a stir bar. DMF (1.05 mL) was added followed by the addition of l-(2- chloroethyl)pyrazole ( 77 mg, 0.593 mmols). The vial was sealed and heated at 120C for 15 minutes. Water (3 mL) was added and the resulting precipitate collected by filtration and washed with 5 mL of water. The filtrate was concentrated under reduced pressure. Each of the collected solid and the residue from concentration of the filtrate was diluted with DMSO until solubilized and purified by reversed-phase HPLC to give 6-(l-(2-(lH-pyrazol-l- yl)ethyl)-lH-pyrazol-4-yl)-2-(5,6-dimethoxypyridin-3-yl)-6,7-dihydro-5H-pyrrolo[3,4- 6]pyridin-5-one (Compound 171, 22 mg, 0.05 mmol, 17% yield): ESMS (Mu+Eta) 432.0; 1H NMR (DMSO-de, 300 MHz) delta 8.47 (d, J = 2.0 Hz, 1H), 8.10 (s, 2H), 7.95-7.87 (m, 2H), 7.75 (s, 1H), 7.45 (d, J = 2.2Hz, 1H), 7.40 (d, J = 1.3 Hz, 1H), 6.12 (t, J = 2.0 Hz, 1H), 4.84 (s, 2H), 4.50 (s, 4H), 3.88 (s, 3H), 3.85 (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, 1-(2-Chloroethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 96450-53-2, These common heterocyclic compound, 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole, 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.

A solution of Boc methylenedioxybenzenesulfonamide free phenol (0.010 g, 0.020 mmol) in acetone (1 ML) was combined with cesium carbonate (0.015 g, 0.047 mmol), 1-(2-chloroethyl)pyrazole (0.004 9, 0.031 mmol) and sodium iodide (~1 mg, 0.007 mmol).The solution was heated to 55 C. with stirring for 60 hours, and was cooled and dried in vacuo to give a yellow oil.Flash column chromatography (1:3 ethyl acetate/hexane) gave Boc methylenedioxybenzenesulfonamide ethylpyrazole tethered product (0.0015 g, 13%) as a colourless oil: Rf=0.20 (1:1 ethyl acetate/hexane); coupled LCMS showed the product as a single major peak with m/z 631 [M+H]+ at RT of 1.65 min.

The synthetic route of 96450-53-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated.; US2004/122000; (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. 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H7ClN2

1 -(2-Chloroethyl)-1 1H-pyrazole was prepared by reacting pyrazole with 1 – bromo-2-chloroethane. Lambda/-[1 -(Fluoromethyl)cyclopropyl]-3-[(1 -methylpyrazol-4-yl)methyl]- 2,4-dioxo-1 H-quinazoline-6-sulfonamide (100 mg, 0.260 mmol), 1 -(2-chloroethyl)-1 H- pyrazole (37 mg, 0.286 mmol) and potassium carbonate (43 mg, 0.312 mmol) in DMF was conventionally heated to 70 C for 4 h. Usual work-up afforded the desired product (7 mg, 0.014 mmol, 5.4%) as a white powder.

According to the analysis of related databases, 96450-53-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole, molecular formula is C5H7ClN2, 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: 1-(2-Chloroethyl)-1H-pyrazole

A mixture of 13.02 g (0.1 mol) of 1-(2-chloroethyl)pyrazole 1, 11.2 g (0.2 mol) of KOH, and 50 mL of 50 wt% aqueous solution of MMO was vigorously stirred during 2 h at 80C. After cooling to ambient, the reaction mixture was extracted with chloroform. The solvent was removed, and the residue was distilled in vacuum. Yield 7.0 g (75%), bp 63C(50 mmHg), nD20 1.5160 [16]. IR spectrum, nu, cm-1:1520 (ring), 1640 (C=C). 1H NMR spectrum, delta, ppm(J, Hz): 5.00 d.d (1H, =CH2, J = 9.0, 1.5), 5.52 d.d(1H, =CH2, J = 15.8, 1.5), 6.26 t (1H, 4-H, J = 2.2),7.12 d.d (1H, NC=H, J = 15.8, 9.0), 7.50 d (1H, 3-H,J = 2.4), 7.58 d (1H, 5-H, J = 2.0).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 96450-53-2, its application will become more common.