Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-Dichloropyrazine, 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 4774-14-5, HPLC of Formula: C4H2Cl2N2

To a -20 C. solution of n-butyllithium (2.5 M in hexane, Aldrich, 26.5 mmol) in dry tetrahydrofuran (200 mL) under argon was added 2,2,6,6-tetramethylpiperidine (Aldrich, 11.5 mL, 66.5 mmol, 1.22 eq). The resulting solution was warmed to 0 C. over 0.5 hour period. The solution was then cooled to -78 C., and a solution of 2,6-dichloropyrazine (Aldrich, 8.24 g, 55.3 mmol, 1.0 eq) in tetrahydrofuran was slowly added via a syringe. After addition was complete, the resulting mixture was stirred at -78 C. for an additional 1 hour after which 2-chlorobenzaldehyde (Aldrich, 9.3 mL, 83 mmole, 1.5 eq) was added drop wise via a syringe. The reaction mixture was stirred for an additional 1 hour, quenched with hydrochloric acid (18 mL, 220 mmol, 4 eq)/ethanol (75 mL)/tetrahydrofuran (90 mL) mixture, and then warmed to room temperature. The reaction mixture was diluted with aqueous saturated sodium bicarbonate solution and extracted with ether. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered, and concentrated to give a crude oil which was purified via chromatography using dichloromethane/hexanes (1:1) as the eluent to give (2-chlorophenyl)-(3,5-dichloropyrazin-2-yl)methanol (12.8 g, 44 mmol, 80% yield). Mass spec, M+1=290.

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Reference:
Patent; Roche Palo Alto LLC; US2005/203091; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-29-5, 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. 33332-29-5, name is 2-Amino-5-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step A: 2-Chloro-5-isothiocyanatopyrazine CINSA solution of 5-chloropyrazin-2-amine (13.0 g, 100 mmol) and 1,1?- thiocarbonyldipyridin-2(1H)-one (27.9 g, 120 mmol) was stirred in DCM (200 mL)at room temperature for 1 h. The reaction was concentrated to ca. 100 mL volume and filtered through a pad of silica gel (1 L), washing with ethyl acetate in hexanes (10%). The filtrate was concentrated and dried to afford 2-chloro-5- isothiocyanatopyrazine (14.3 g, 83.0 mmol, 83 % yield). ?H NMR (400 MHz, chloroform-cl) 5 ppm 8.38 (d, J=1.26 Hz, 1 H) 8.18 (d, 1=1.26 Hz, 1 H). MS(LC/MS) R.T. = 1.84; [M+H] = 172.09.

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-Amino-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HILL, Matthew D.; FANG, Haiquan; WO2013/177024; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 19745-07-4,Some common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

Preparation of 4-benzyl- 1 -(5-chloropyrazin-2-yl)piperidin-4-amine. To a solution of 2,5-dichloropyrazine (0.1316 mL, 0.7243 mmol) in DMSO (10 mL) were added K2CO3 (300.3 mg, 2.173 mmol) followed by 4-benzylpiperidin-4-amine bis(2,2,2- trifluoroacetate) (303 mg, 0.72 mmol). The reaction was sealed and heated at 75 °C overnight. After cooling to RT, the reaction was diluted with EtOAc (10 mL) and water (20 mL). After phase-separation, the aqueous was extracted with EtOAc (2x). The combined organic extracts were concentrated and used directly in the next step. MS (apci) m/z = 303.1 (M+H).

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

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 89180-45-0,Some common heterocyclic compound, 89180-45-0, name is 5-Chloro-2-hydroxypyrazine, molecular formula is C4H3ClN2O, 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 50 mL round bottom flask equipped with a stir bar was added 5- chloropyrazin-2-ol (250 mg, 1.9 15 mmol), 2-(4-fluorophenyl)ethanol (268 mg, 1.9 15 mmol), triphenylphosphine (603 mg, 2.298 mmol) and THF (10 mL). To the stirred solution was added DIAD (0.447 mL, 2.298 mmol). The solution had a mild exotherm, then cooled within 5 minutes. The solution was stirred at RT for 2 hrs. The reactionsolution was concentrated in vacuo and the resulting oil was purified via silica gel chromatography (40 g column, 5-40% EtOAc:Hex) to afford the product 2-chloro-5-(4-fluorophenethoxy)pyrazine (330 mg, 1.306 mmol, 68.2 % yield) as a white solid. ?H NMR (500 MHz, CDC13) 8.10 (d,J=1.3 Hz, 1H), 8.01 (d,J=1.3 Hz, 1H), 7.25 (dd, J=8.6, 5.4 Hz, 2H), 7.03 (t, J=8.7 Hz, 2H), 4.52 (t, J=6.9 Hz, 2H), 3.09 (t, J=6.9 Hz, 2H). LCMS (M+1) = 253.0.

The synthetic route of 89180-45-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 27398-39-6

To a suspension of 3-chloropyrazine-2-carboxylic acid (5.46 g) in THF (100 mL) was added CDI (6.14 g) at room temperature, and the mixture was stirred at room temperature for 30 min and heated to 50 °C. After stirring at 50 °C for 1 h, the mixture was cooled to room temperature. To the mixture were added N, O-dimethylhydroxylamine hydrochloride (5.04 g) and DIPEA (9.02 mL) at room temperature, and the mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (3.05 g) .MS (API+) : [M+H]+ 202.1.H NMR (300 MHz, CDC13) delta 3.43 (3H, s) , 3.58 (3H, s), 8.44 (1H, d, J = 2.3 Hz>, 8.52 (1H, d, J = ‘2.3 Hz).

The synthetic route of 27398-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RAKER, Joseph; TANIGUCHI, Takahiko; YOSHIKAWA, Masato; HASUI, Tomoaki; KUNITOMO, Jun; WO2012/18909; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid, 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 1174321-06-2, Safety of 5-(Difluoromethyl)pyrazine-2-carboxylic acid

Step 9: tert- Butyl ((4aS,5SJaS)-7a-(5-(5-(difluoromethyl)pyrazine-2-carboxamido)-2- fluorophenyl)-3-methyl-4-oxo-5-(trifluoromethyl)-3,4,4a,5J,7a-hexahydrofuror3,4- dlpyrimidin-2-yl)carbamate N- Ethyl-N-(propan-2-yl)propan-2- amine (300 muL, 1.7 mmol) was added to a stirred mixture of tert-butyl ((4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-3-methyl-4-oxo-5- (trifluoromethyl)-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate amine (150 mg, 0.34 mmol), 5-(difluoromethyl)pyrazine-2-carboxylic acid (90 mg, 0.50 mmol) and (lH-benzotriazol-l-yloxy)(tripyrrolidin-l-yl)phosphoniumhexafluorophosphate (265 mg, 0.50 mmol) in dry DCM (2 mL) at RT under nitrogen. The reaction was stirred at this temperature for 16 h, then partitioned between DCM and NaHCO3 (aq). The aqueous layer was extracted with DCM (x2). The combined extracts were dried by passing through a hydrophobic frit and then evaporated. The residue was purified by column chromatography (normal phase, 25 g, Biotage SNAP cartridge KP-SiI, 25mL per min, gradient 5% to 30% EtOAc in n-hexane) to give the title compound (92 mg, light yellow solid). 1H NMR (400 MHz, CDCl3) delta ppm 1.58 (s, 9H) 3.36 (s, 3H) 4.06 (d, J=7.83 Hz, IH) 4.40 (d, J=9.85 Hz, IH) 4.50 (dd, J=9.73, 2.91 Hz, IH) 4.57 – 4.65 (m, IH) 6.81 (t, J=54.60 Hz, IH) 7.22 (dd, J=10.86, 9.09 Hz, IH) 7.74 (dd, J=6.69, 2.65 Hz, IH) 7.84 (ddd, J=8.84, 4.17, 2.65 Hz, IH) 8.93 (s, IH) 9.52 (s, IH) 9.65 (s, IH) 10.64 (s, IH)

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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

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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromopyrazine

A solution of 1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1H-pyrazol-4-ylboronic acid (50 mg, 0.10 mmol), 2- bromopyrazine (20 mg, 0.12 mmol), Pd(PPh3)4 (12 mg, 0.10 mmol), Na2CO3 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H2O (4:1, 2.1 mL) was heated at 85 C for 18 hours. LiOH (12.4 mg, 0.52 mmol) was added and the reaction was heated at 90 oC under microwave radiation for 15 minutes.1 N HCl (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by reverse chromatography on C-18 column using a solution of MeCN in water (containing 10 mM of NH4CO2H) (30 to 70%). The product was lyophylised and afforded the title compound (10 mg, 0.020 mmol, 20%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) delta 8.97 (s, 1H), 8.71 (s, 1H), 8.58 (s, 1H), 8.23 (d, J = 1.9 Hz, 1H), 8.04 (dd, J = 8.4, 2.0 Hz, 1H), 7.76 (d, J = 8.5 Hz, 1H), 3.36 (hept, J = 6.7 Hz, 1H), 2.47 (s, 3H), 1.24 (d, J = 6.7 Hz, 6H); MS (m/z): 505.9 [M+H]+.

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M., Arshad; CIBLAT, Stephane; DERY, Martin; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu; SRIVASTAVA, Sanjay; SHIPPS, Gerald, W.; COOPER, Alan, B.; BRUNEAU-LATOUR, Nicolas; LY, Vu, Linh; (314 pag.)WO2016/196644; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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 mixture of 2-chloropyrazine (4.00 g) and hydrazine hydrate was heated at 110 C. for 1 h, and then cooled to room temperature. The mixture was filtered to give the title compound as a solid (2.30 g, 60.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 111.0 (M+1).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 109838-85-9, 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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step A – Preparation of Compound Int- 13cA 5 L- 3 necked round bottomed flask, equipped with a mechanical stirrer, temperature probe, addition funnel and N2 inlet, was charged with the Schollkopf chiral auxiliary-(Int-13a, 200 g, 1.09 mol, 1.0 eq), bis(chloromethyl) dimethylsilane (Int-13b, 256 g, 1.63 mol, 1.5 eq), and THF (2 L, Aldrich anhydrous). The flask was cooled in a dry ice/ 2- propanol bath until the internal temperature reached -75 °C. n-Butyllithium (Aldrich 2.5 M in hexanes , 478 mL, 1.19 mol, 1.09 eq) was added via a dropping funnel over 1 hour while maintaining the internal reaction temperature between -67 °C and -76 °C. The resulting orange-red solution was allowed to gradually warm to room temperature for about 15 hours. The reaction mixture was then re-cooled to 0 °C and quenched with 500 mL of water.Diethyl ether (2L) was added and the layers were separated. The aqueous layer was extracted with 1 L of diethyl ether. The combined organic layers was washed with water and brine, dried with MgS04, filtered, and concentrated in vacuo to dryness, giving 480 g of orange oil. This material was left in vacuo for about 15 hours to provide 420 g of oil. The crude product was split into two batches and purified via silica gel chromatography on a 1.6 kg flash column. The column was eluted with gradient of 0-4percent Et20 in hexanes. The product fractions were concentrated in vacuo at a bath temperature at or below 40 °C giving 190 grams of Int-13c-(60percentyield).

The synthetic route of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DWYER, Michael P; KEERTIKAR, Kartik M; COBURN, Craig A; WU, Hao; HU, Bin; ZHONG, Bin; ZHANG, Chengren; DAN, Zhigang; TONG, Ling; YU, Wensheng; WO2012/41227; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 98-97-5, The chemical industry reduces the impact on the environment during synthesis 98-97-5, name is Pyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a solution of pyrazine-2-carboxylic acid (1.36 g, 10.9 mmol, 1 eq.) in SOCl2 (20 mL) was added DMF (2 drops). The mixture was stirred at 60 C. for 20 min. The volatiles were removed in vacuo to give crude pyrazine-2-carbonyl chloride, which was used in the next step directly. To a suspension of 2-amino-5-nitrobenzoic acid (2.00 g, 10.9 mmol, 1.0 eq.) in THF (50 mL) was added Et3N (1.09 g) and pyrazine-2-carbonyl chloride in anhydrous THF (50 mL) dropwise. The resulting mixture was stirred at room temperature for 18 h. After the reaction was completed, the volatiles were removed. The residue was suspended in H2O (10 mL) and the pH was adjusted to 5 by slow addition of 2N HCl in water. The resulting solid was collected and dried in vacuo to give 3.12 g of 5-nitro-2-(pyrazine-2-carboxamido)benzoic acid as a brown solid (99%). LCMS m/z=289.0 (M+1) (Method B) (retention time=1.24 min)

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

Reference:
Patent; Suzuki, Masaki; Kondo, Kazumi; Kurimura, Muneaki; Valluru, Krishna Reddy; Takahashi, Akira; Kuroda, Takeshi; Takahashi, Haruka; Fukushima, Tae; Miyamura, Shin; Ghosh, Indranath; Dogra, Abhishek; Harriman, Geraldine; Elder, Amy; Shimizu, Satoshi; Hodgetts, Kevin J.; Newcom, Jason S.; US2015/307477; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem