Tag: M.W=100-200

Electric Literature of 33332-25-1, A common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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.

This compound was prepared by following Suzuki coupling mechanism where methyl 5-(chloropyrazine)-2-carboxylate, a commercially available starting material 36 7 (2g, 0.0115mmol) was reacted with 44 phenyl boronic acid (1.4g, 0.0115mmol) using 45 bis(triphenylphosphine) palladium(II)dichloride (0.163g, 0.0002mmol) as catalyst, 146 potassium carbonate (2.4g, 0.01737mmol) as base and 1,4-dioxane as solvent for 12h at 100C. After completion of the reaction, the solvent was evaporated and crude was extracted in 106 ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and crude was purified by column chromatography (hexane: EtOAc; 9:1) to get 1g of pure white crystalline solid intermediate 47 19 (yield 40.16%). 1H NMR (400MHz, DMSO-d6) delta 9.42 (d, J=1.4Hz, 1H), 9.25 (d, J=1.4Hz, 1H), 8.27-8.23 (m, 2H), 7.62-7.57 (m, 3H), 3.95 (s, 3H). C12H12N2O2 [M]: 214.22; MS (ESI) m/z: [M+H]+: 215.10.

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Trivedi, Prakruti; Adhikari, Nilanjan; Amin, Sk. Abdul; Jha, Tarun; Ghosh, Balaram; European Journal of Pharmaceutical Sciences; vol. 124; (2018); p. 165 – 181;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

2-Amino 5-cyano pyrazine (0.25 g, 2.08 mmol) was dissolved in THF and DCM (3:1 , 40 ml_) and pyridine (0.49 g, 6.2 mmol) was added. The mixture was stirred for 15 minutes. Phenylchloroformate (0.97 g, 6.2 mmol) was added and the reaction mixture was heated at 50C for 2 hours. The reaction mixture was cooled to RT and DCM (40 mL) and water (25 mL) were added. The separated organic layer was washed with water (2 x 25 mL), brine (25 mL), dried (Na2S04) and the solvents evaporated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 15-20% EtOAc in hexane to give the title compound (0.29g, 54%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminopyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert George; WALKER, David Winter; BOYCE, Richard Justin; WO2011/141716; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

54608-52-5, name is 2-Hydrazinopyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C4H6N4

In a 8 mL vial with magnetic stirrer and screw cap, ethyl 4-chloro-7- methoxyquinoline-3-carboxylate (70 mg, 0.26 mmol, 1 equiv.) and 2-hydrazinopyrazine (32 mg, 0.29 mmol, 1.1 equiv.) were dispersed in 1.5 mL ethanol, triethylamine (40 muL, 0.29 mmol, 1.1 eq.) was added and the reaction mixture was heated to reflux under argon atmosphere. After 20 h the reaction mixture was rinsed with 4 mL water, filtered and the precipitate was washed with 15 mL EtOAc/PE (1/1). The yellow solid was dried under reduced pressure to give the desired product. Yield: 58% (0.15 mmol, 45 mg), Appearance: yellow solid, TLC: 0.38 (10% MeOH in CH2Cl2), M.p.: >300 C, 1H NMR (400 MHz, DMSO- d6) delta 3.88 (s, 3H), 7.16- 7.23 (m, 2H), 8.13 (dd, J = 8.5, 0.8 Hz, 1H), 8.44 (d, J = 2.5 Hz, 1H), 8.56 (dd, J = 2.5, 1.5 Hz, 1H), 8.75 (s, 1H), 9.51 (d, J = 1.4 Hz, 1H), 12.74 (br s, 1H).13C NMR (101 MHz, DMSO-d6) delta 55.6 (q), 102.1 (d), 105.0 (s), 112.2 (s), 115.5 (d), 123.9 (d), 136.6 (d), 137.3 (s), 140.0 (d), 140.1 (d), 142.8 (d), 144.9 (s), 148.0 (s), 160.8 (s), 162.4 (s). HR-MS: Calc.[M+H]+ m/z (predicted) = 294.0992, m/z (measured) = 294.0992, difference = 0.00 ppm.

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UWM RESEARCH FOUNDATION, INC.; MEDICAL UNIVERSITY OF VIENNA; NATIONAL TAIWAN UNIVERSITY; UNIVERSITY OF BELGRADE-FACULTY OF PHARMACY; CHIOU, Lih-Chu; COOK, James; ERNST, Margot; FAN, Pi-Chuan; KNUTSON, Daniel; MEIRELLES, Matheus; MIHOVILOVIC, Marko; SIEGHART, Werner; VARAGIC, Zdravko; VERMA, Ranjit; WIMMER, Laurin; WITZIGMANN, Christopher; SIEBERT, David, Chan Bodin; SAVIC, Miroslav, M.; (170 pag.)WO2016/196961; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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. Safety of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

To a solution of 2-bromo-5H-pyrrolo[3,2-Z?]pyrazine (0.68 g, 3.4 mmol) in acetone (17 mL) was added N-iodosuccinimide (0.82 g, 3.6 mmol) and the resulting mixture was stirred for 4 h at rt. The mixture was evaporated in vacuo to yield a residue that was purified via silica gel chromatography eluting with 40% THF in hexanes to give the title compound as a yellow solid (0.99 g, 89%). NMR (DMSO-i , 300 MHz): delta 12.82 (s, 1H), 8.42 (s, 1 H), 8.20 (s, 1 H). HPLC retention time: 2.23 minutes. MS ESI (m/z): 324.0, 326.0 (M+H)+, calc. 323.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF ROCHESTER; BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA; GELBARD, Harris A.; DEWHURST, Stephen; GENDELMAN, Howard E.; WO2014/85795; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1174321-06-2, A common heterocyclic compound, 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid, molecular formula is C6H4F2N2O2, 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 an ice-water cooled mixture of tert-butyl[(4’R)-6′-amino-2′,2′-dimethyldispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl]carbamate (430 mg, 1.15 mmol), 5-(difluoromethyl)pyrazine-2-carboxylic acid (221 mg, 1.27mmol) and lH-benzotriazol-1-ol (170 mg, 1.26 mmol) in chloroform (8.6 ml) was addedN-[3-(dimethylamino)propyl]-N’-ethylcarbodiimide hydrochloride (244 mg, 1.28 mmol). Themixture was stirred at room temperature overnight and directly purified by silica gel columnchromatography (precolumn: basic silica gel, main column: neutral silica gel, hexane/ethylacetate= 2:1- 1:1- 0:100) to afford tert-butyl[ ( 4’R)-6′-( { [5-( difluoromethyl)pyrazin-2-yl]carbonyl }amino )-2′ ,2′-dimethyldispiro[ cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl]carbamate (373 mg).

The synthetic route of 1174321-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTELLAS PHARMA INC.; COMENTIS, INC.; MUNAKATA, Ryosuke; INOUE, Makoto; TOMINAGA, Hiroaki; YAMASAKI, Shingo; SHIINA, Yasuhiro; SAMIZU, Kiyohiro; HAMAGUCHI, Hisao; HONG, Lin; WO2013/181202; (2013); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 108-50-9, name is 2,6-Dimethylpyrazine, 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 108-50-9, Recommanded Product: 108-50-9

Example 12 [00659] Preparation of Cpd 88 H2 N 150 C / 3 days N [00660] Part 1, Step A: To a cooled solution of 2,6-dimethylpyrazine (108 g, 1.0 mol) in DMF (260 mL) on an ice/H20 bath, while stirring vigorously, was added sulfuryl chloride (270 mL, 3.3 mol). The rate of addition was controlled to maintain the reaction temperature between 40-60 C for about 2 hours. After the addition, the cooling bath was removed and the mixture was stirred for an additional 0.5 hours. LC/MS analysis of an aliquot showed <5% starting material remained. The reaction mixture was then cooled in an ice/water bath and, while maintaining the temperature below 35 C, quenched carefully with 10 M NaOH (1 L), followed by the addition of Na2C03 (solid) to pH 6. After the addition of water (800 mL), the mixture was distilled. The distillate was collected and the organics were separated. The aqueous layer was extracted with ethyl ether (100 mL x 3) and the ether extracts were combined with the organics separated previously. The combined extracts were washed with water (30 mL x 3), then brine and dried over Na2S04. After the extracts were concentrated, the residue was distilled and the product was collected as a colorless liquid, approximate boiling point: 127 C at 154 mmHg (99.1 g, 69%). 1H NMR (500 MHz, CHLOROFORM- ) delta ppm 8.05 (1H, s), 2.61 (3H, d, J=0.63 Hz), 2.50 (3H, s). 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, 2,6-Dimethylpyrazine, other downstream synthetic routes, hurry up and to see. Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; DAKKA, Amal; KARP, Gary Mitchell; LI, Chunshi; NARASIMHAN, Jana; NARYSHKIN, Nikolai; WEETALL, Maria L.; WELCH, Ellen; ZHAO, Xin; WO2013/112788; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid, 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. category: Pyrazines

Step 12: (+/-)-N-(3-((4aS*,7aS*)-2-amino-3-methyl-4-oxo-3,4,4a,5,7,7a-hexahydrofuro r3,4-dlpyrimidin-7a-yl)-4-fluorophenyl)-5-(difluoromethyl)picolinamide.(+/-)-tert-Butyl ((4aS*,7aS*)-7a-(5-amino-2-fluorophenyl)-3-methyl-4-oxo-3,4,4a,5,7,7a- hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (11 mg , 0.03 mmol) was dissolved in DCM (2 mL). 5-(difluoromethyl)pyrazine-2-carboxylic acid (8 mg , 0.04 mmol) was transferred into the reaction vessel. N-ethyl-N-(propan-2-yl)propan-2-amine (7.5 mg, 0.06 mmol) was transferred in to the reaction vessel. N-[3-(dimethylamino)propyl]- N’-ethylcarbodiimide (7 mg, 0.04 mmol) was transferred into the reaction vessel.After 15 mins the reaction mixture was washed with HCl (IM, 2 x 2 mL) then with saturated aqueous NaHCO3 (2 x 2 mL). The organic phase was then concentrated and the crude mixture was taken directly to the next reaction. LCMS (Method A) Rt 5.44 min; ESI-MS: m/z 535 [M+H]+.

The synthetic route of 5-(Difluoromethyl)pyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD; CASTRO PINEIRO, Jose, Luis; HALL, Adrian; MADIN, Andrew; VO, Ngoc-Tri; WO2011/9897; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6863-73-6, name is 3-Chloropyrazin-2-amine, 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 6863-73-6, Recommanded Product: 3-Chloropyrazin-2-amine

Step B: Preparation of 8-chloro-imidazo[ 1 ,2-a]pyrazine To a stirred suspension of 3-chloropyrazin-2-amine (107.5 g, 129.6mmol) in water (2500 mL) and THF (236 mL) at rt was added ethyl 2-bromo-1 ,1 -diethoxyethane (375 mL, 197 mmol) in one portion. After stirring at reflux for 4 h and 5 h at rt, the solution was adjusted to pH 8 by potassium carbonate, extracted with DCM (4 x 1000 mL9, dried over sodium sulphate, filtered and evaporated. Yield 132.9 g (104 %) 8-chloro-imidazo[1 ,2-a]pyrazine: 1H-NMR (300 MHz, d6-DMSO): delta =8.62 (d, 1 H), 8.24 (d, 1 H), 7.82 (d, 1 H), 7.69 (d, 1 H) ppm.

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, 3-Chloropyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80229; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 875781-43-4, 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2-Bromo-5H-pyrrolo[3,2-b]pyrazine(4; 0.471 g,2.39 mmol), 4-pyridylboronic acid (0.58 g, 4.72 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloromethane adduct (0.097 g, 0.12 mmol), acetonitrile(3 mL) and 1M sodium carbonate (3 mL) were placed in a 10 mL CEM microwavevial. The vial was capped and irradiated in a CEM microwave reactor for 30minutes at 150 C.Water (3 mL) and ethyl acetate (9 mL) were added the layers were partitioned. Theaqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organicextracts were washed with saturated sodium chloride (5 mL), dried over MgSO4and concentrated under reduced pressure. The residue was purified by preparativereverse phase HPLC to give 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine(14; 0.28 g,60%) as an off white solid: 1H NMR (400 MHz, DMSO-d6) delta 12.24 (s, 1H), 9.00(s, 1H), 8.69 (dd, J = 4.5, 1.6 Hz, 2H), 8.12 (dd, J = 4.5, 1.6Hz, 2H), 7.98 (d, J = 3.6 Hz, 1H), 6.74 (d, J = 3.6 Hz, 1H); ESMSm/z 197.1 (M+1).

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Burdick, Daniel J.; Wang, Shumei; Heise, Christopher; Pan, Borlan; Drummond, Jake; Yin, Jianping; Goeser, Lauren; Magnuson, Steven; Blaney, Jeff; Moffat, John; Wang, Weiru; Chen, Huifen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 21; (2015); p. 4728 – 4732;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 23688-89-3, The chemical industry reduces the impact on the environment during synthesis 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

Step 1: tert-Butyl ((trans)-3-(6-chloropyrazine-2-carboxamido)cyclobutyl)carbamate A stirred solution of 6-chloropyrazine-2-carboxylic acid (0.25 g, 1.58 mmol) in DMF (3 mL) was added with DIPEA (0.42 mL, 2.37 mmol) and HATU (0.72 g, 1.9 mmol). The reaction mixture was stirred at room temperature for 20 minutes. A solution of tert-butyl (trans-3-aminocyclobutyl)carbamate (0.32 g, 1.74 mmol) in DMF (3 mL) was added and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and was washed sequentially with saturated aqueous sodium hydrogen carbonate (*2) and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford the title compound (0.530 g, 93%). 1H NMR (400 MHz, DMSO-d6); delta 9.18 (d, J=7.5 Hz, 1H), 9.11 (s, 1H), 9.01 (s, 1H), 7.30 (d, J=7.0 Hz, 1H), 4.54-4.49 (m, 1H), 4.08-4.01 (m, 1H), 2.70 (s, 1H), 2.48-2.39 (m, 2H), 2.27-2.19 (m, 2H), 1.40 (s, 9H).

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, 6-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; Rizzi, Andrea; Carzaniga, Laura; Linney, Ian; Knight, Chris; Schmidt, Wolfgang; (120 pag.)US2018/16267; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem