Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 144692-85-3, name is 2,3-Dichlorofuro[3,4-b]pyrazine-5,7-dione, belongs to Pyrazines 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 144692-85-3, Safety of 2,3-Dichlorofuro[3,4-b]pyrazine-5,7-dione

Under nitrogen, 25ml single neck flask was added 2,3-dichloro-o-pyrazine dicarboxylic anhydride 145 (2.8mmol), cyclohexylamine hydrochloride (4.8mmol), or n-butylamine hydrochloride (4.8mmol), and 5ml of acetic anhydride, the reaction at 120 1.5h, TLC showed the reaction was complete, the reaction was poured into water, solid precipitated, suction filtration, the solid was separated by column chromatography to give a white product.2,3-dichloro-6-cyclohexyl–5H- pyrrolo [3,4-b] pyrazine -5,7 (6H) – dione 146a, yield 67%.

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, 2,3-Dichlorofuro[3,4-b]pyrazine-5,7-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Capital Normal University; Liao, Yi; Zhu, Rui; Tong, Linlin; Guo, Zhangbin; (14 pag.)CN105669704; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 1196152-38-1 as follows. Application In Synthesis of 2-Bromo-5-(trifluoromethyl)pyrazine

example 3o (100 mg, 0.55 mmol), 2-Chloropyrimidine (76.3 mg, 0.67 mmol) and N,N- diisopropylethylamine (192 mu, 1.11 mmol) are dissolved in 1 ml of DMSO and the reaction mixture is heated in a microwave reactor 30 minutes at 120C. The crude product is partitioned between Et20 and water; the organic layer is then separated and concentrated under reduced pressure to obtain the title compound (158 mg). UPLC-MS (Method 2): Rt = 0.76 MS (ES+): m/z = 259 [M+H]+ . Example 30a is synthesized as described for example 28a using example 3o (600 mg, 3.3 mmol), 2-Bromo-5-(Trifluoromethyl)pyrazine (907 mg, 4.0 mmol) instead of 2- Chloropyrimidine, N,N-diisopropylethylamine (1.1 ml, 6.7 mmol) and 8 ml of DMSO. The mixture is heated in a microwave reactor at 100C during 2.5 hours. The crude product is partitioned between EtOAc and water then the organic layer is separated and concentrated under reduced pressure; the residue is purified by Silica gel flash chromatography, using EtOAc/Cyclohexane 1 : 1 to EtOAc 100% as eluent, to obtain the title compound (800 mg, 72 % yield). HPLC-MS (Method 5): Rt = 3.21 MS (APCI+): m/z = 327 [M+H]+ .

According to the analysis of related databases, 1196152-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, belongs to Pyrazines 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 41270-66-0, Recommanded Product: 5-Chloro-2,3-diphenylpyrazine

5 gm of 2-chloro-5,6-diphenylpyrazine (IV) in 25 ml N-Methyl-2-pyrrolidone (NMP) and 5.18 gm of K2CO3 were mixed with 9.92 gm of 4-(isopropylamino)-l-butanol (III), the reaction mixture was then heated with stirring at 150-155 C for 20-21 hrs. The reaction solution was air-cooled, poured into 25 ml water, extracted with 20 ml ethyl acetate. Aqueous layer washed with 10 ml ethyl acetate. Ethyl acetate layers are combined and washed with 15 ml of water, dried over anhydrous magnesium sulfate and then concentrated to obtain 6.3 gm of residue. 6 gm of the residue was purified by silica gel column chromatography by eluting with 2000 ml hexane and 550 ml ethyl acetate to obtain solid 3.2 gm of the desired compound. Yield: 49.41 %

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; LUPIN LIMITED; RAY, Purna, Chandra; KUMAR, Gaurav; SHABADE, Samir, Shanteshwar; RASHINKAR, Dattatray, Bajirao; ARORA, Surinder, Kumar; SINGH, Girij, Pal; (23 pag.)WO2017/60827; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 21943-17-9, A common heterocyclic compound, 21943-17-9, name is 5-Bromo-3-chloropyrazin-2(1H)-one, molecular formula is C4H2BrClN2O, 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: A solution of 56 (1.50 g, 7.16 mmol), the appropriate secondary amine (8.59 mmol, 1.20 equiv) and diisopropylethylamine (1.50 mL, 8.59 mmol) in n-butanol (15 mL)was heated in a microwave reactor using variable wattage to 140 C for 1 h. The mixture was concentrated and purified by flash column chromatography on silica, eluting with 9:1 dichloromethane/methanol, to give gave 58-63.

The synthetic route of 21943-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, belongs to Pyrazines 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 221136-66-9, Recommanded Product: 221136-66-9

STEP A: r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin- 1-yll-acetic acidA 4-neck round bottom flask, equipped with thermometer, and addition funnel, is charged with 3-bromo-6-methyl-2-oxo-2H-pyrazin-1-yl)-acetic acid ethyl ester (44.00 g, 160.0 mmol), anhydrous Na2HPO4 (31.8 g, 224 mmol), and n-butanol (210 g). 2,2-Difluoro-2-phenyl-ethylamine (30.15 g, 192 mmol) is then added in one portion. The resulting suspension is heated to reflux over 30 – 90 min and further stirred for 12 – 16 h. The suspension is cooled to 75- 9O0C over 30-60 min, and water (130 g) is added over 15-30 min, resulting in a clear 2-phasic reaction mixture. 30% NaOH(aq) ( 95.2 g, 714 mmol) is added and the reaction mixture is further stirred for 60 min at 75-850C. After completion of the hydrolysis, 32/34% HCI (aq) (85 g, 778 mmol) is added dropwise, resulting in the precipitation of the product. Complete precipitation is achieved by cooling the suspension to 0-100C and stirring at this temperature for additional 30 min. The product ([3-(2,2-Difluoro-2-phenyl-ethylamino)-6- methyl-2-oxo-2H-pyrazin-1 -yli-acetic acid) is centrifuged and washed with water (100 g) and then with a mixture of ethanol (40 g) and water (50 g). The isolated product is then vacuum dried at 40-600C.Note: Step A may alternatively be completed by reacting the 3-bromo-6- methyl-2-oxo-2H-pyrazin-1-yl)-acetic acid ethyl ester with the HCI salt of 2,2- difluoro-2-phenyl-ethylamine. In this case, an aqueous work-up with TBME and 30% NaOH(aq) is required to isolate the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 6966-01-4 as follows. category: Pyrazines

The compound 3-amino-6-bromopyrazine-2-carboxylic acid methyl ester 3a (20.0 g, 86.2 mmol) was added to a 500 mL three-necked flask, dioxane (40mL), HBr (200mL) and acetic acid (40mL), stirred and dissolved -5 C dropwise to the reaction system was added NaNO2 (19.6g, 285mmol), the solution was stirred at -5 C (20mL) acetic acid for 4 hours. The system was poured into a solution of Na2SO3 and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, and dried under reduced pressure using a rotary evaporator, purified by column to give the title compound 3b (12.0g, 40.8mmol), in a yield of 47.3%

According to the analysis of related databases, 6966-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 32111-21-0, 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. 32111-21-0, name is 2-Iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Pd2(dba)3 -CHCl3 (5 mg, 0.5 mol %), 2′-(dicyclohexylphosphino)biphenyl-2-amine (8 mg, 2 mol %) and sodium tert-butoxide (13 mg, 0.14 mmol) were weighed in air and transferred into flask, followed by dioxane (750 muL), 1 ‘-(piperidin-4- yl)spiro[benzo[d][l,3]oxazine-4,4’-piperidin]-2(lH)-one bis-hydrochloride (compound no. 49) (37 mg, 0.10 mmol) and iodopyrazine (viia). (20.6 mg, 0.10 mmol). The flask was flushed with nitrogen and stirred at 800C for 16 hours. The reaction mixture was diluted with methanol (500 muL), filtered (Whatman 0.45 mum PTFE) and subjected to reverse-phase HPLC purification (2-25% CH3CN gradient [w/ 0.1% TFA (aq)] over 10 minutes, 1.0 mL injected, 35 mL/min) to provide l’-(l-(pyrazin-2-yl)piperidin-4- yl)spiro[benzo[d][l,3]oxazine-4,4′-pirhoeridin]-2(lH)-one (compound no. 74). LC/MS m/z 380.2 [M+H]+, retention time 1.35 min (RP-Cl 8, 10-99% CH3CN/0.05% TFA).

The chemical industry reduces the impact on the environment during synthesis 2-Iodopyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/21375; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 61655-77-4, name is 2-Chloro-6-(4-methylpiperazin-1-yl)pyrazine, belongs to Pyrazines 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 61655-77-4, HPLC of Formula: C9H13ClN4

EXAMPLE 87: 5-(6-(4-methylpiperazin-l-yl)pyrazin-2-yl)-lH-pyrrolor2,3-b1pyridineThe starting material 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (124) (50 mg, 0.2 mmol, 1 eq) and 2-chloro-6-(4-methylpiperazin-l-yl)pyrazine (63) (44 mg, 0.2 mmol, 1 eq) in DMF (5 mL) was degassed and purged under argon atmosphere for 10 min. To this reaction mixture was charged Cs2C03 (133 mg, 0.4 mmol, 2 eq) followed by addition of Pd(PPh3)4 (0.01 mg, 0.04 mmol) and degassing and purging under argon for an additional 10 min. The reaction mixture was heated at 100C for 12 h in a sealed tube. After completion of the reaction, the reaction mixture was diluted with CHC13 and filtered through Celite. The solvents were distilled off and the crude material was submitted for flash column purification in neutral alumina using 2% MeOH/CHCl3 to obtain pale yellow solid compound 5-(6-(4- methylpiperazin-l-yl)pyrazin-2-yl)-lH-pyrrolo[2,3-b]pyridine 125 in 20 mg quantity. The compound 125 was confirmed by 1HNMR and LCMS. 1H NMR (400 MHz, CDC13) delta: 8.96 (d, J=1.5Hz 1H), 8.55 (d, J=1.70Hz, 1H), 8.30 (s, 1H), 8.08 (s,lH), 7.35 (m, J=3.04, 1H), 6.60(m, J=1.95 1H), 3.75 (m, J=5.00, 4H), 2.58 (m, J=5.12, 4H), 2.38 (s , 3H); MS m/z 294.9 (M+H)+.

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, 2-Chloro-6-(4-methylpiperazin-1-yl)pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Preparation of Intermediate I-02. A solution of intermediate I-01(15 g, 59.3 mmol) in morpholine (15 ml, 178 mmol) was heated at 120 C. in a Parr reactor for 48 h. A brown solid appears. The solid was suspended in DCM and washed with NaHCO3 aq. sat (twice). The organic phase was dried (NaSO4), filtered and evaporated to dryness to obtain 1-02, 14.8 g of a brown solid (Y: 96%)

The synthetic route of 2-Amino-3,5-dibromopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1458-16-8, 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. 1458-16-8, name is Methyl 3-amino-6-iodopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

30 ml of ammonia in water is added under magnetic stirring to 15 g (53.8 mmol) of a solution of methyl 3-amino-6-iodopyrazine-2-carboxylate in 150 ml of methanol. The reaction medium is stirred at 25C for 48 hours. After evaporation of the solvents, the precipitate obtained is filtered, rinsed with water and then dried at 50C to yield 12.50 g of 3-amino-6-iodopyrazine-2-carboxamide (88%) in the form of a beige solid. LCMS (EI, m/z): (M+1) 265.02 1H NMR: deltaH ppm (400 MHz, DMSO): 8.35 (1H, s, CHarom), 7.85 (1H, bs, NH), 7.60 (3H, bs, NH), 3.25 (3H, s, CH3)

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-6-iodopyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Sokoloff, Pierre; Cachoux, Frederic; EP2689778; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem