Tag: M.W=100-200

Reference of 136927-64-5, These common heterocyclic compound, 136927-64-5, name is 1-Chloropyrrolo[1,2-a]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.

To a solution of the product of Example 4 A in dioxane (lmL) were added 1- chloropyrrolo[l,2-a]pyrazine (64.3 mg, 0.421 mmol), palladium(II) acetate (7.89 mg, 0.035 mmol), xantphos (20.3 mg, 0.035 mmol), and potassium carbonate (146 mg, 1.05 mmol). The reaction mixture was heated at 80 C for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified with flash column chromatography (Si(, heptane:ethyl acetate 0-100%) followed by preparative HPLC [Waters XBridge C18 5 mupiiota OBD column, 30 x 100 mm, flow rate 40 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (8 mg, 0.020 mmol, 6% yield). JH NMR (400 MHz, DMSO-<) delta ppm 8.92 (s, 1H), 7.88 (d, J = 5.7 Hz, 1H), 7.86 - 7.82 (m, 1H), 7.52 (d, J = 4.3 Hz, 1H), 7.47 (t, J = 8.8 Hz, 1H), 7.05 (dd, J = 11.3, 2.9 Hz, 1H), 7.00 (d, J = 5.7 Hz, 1H), 6.87 - 6.81 (m, 2H), 4.51 (s, 2H), 2.57 (s, 6H); MS (ESI+) m/z 401 (M+H)+. Statistics shows that 1-Chloropyrrolo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 136927-64-5. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 87486-33-7, These common heterocyclic compound, 87486-33-7, name is 3,5-Dichloro-1-methylpyrazin-2(1H)-one, 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: 6?-Chloro-4?-methyl-4-(2-trifluoromethyl-benzoyl)-3,4,5,6-tetrahydro-2H,4?H-[1,2?]bipyrazinyl-3?-one (1)[0262][0263]Compound 1 is prepared according to synthesis method 1: 1.76 g (5.97 mmoles) of derivative 1 h and 1.13 g (6.31 mmoles) of pyrazinone 4c are placed in 3 ml of butanol-1 in the presence of 4 ml (27.9 mmoles) of NEt3. This mixture is stirred at 120 C. for 24 hours. After concentrating the reaction medium to dryness, the residue obtained is taken up with AcOEt and washed with water and with a saturated NaCl solution. After drying on MgSO4, the organic phase is concentrated to dryness. The residue obtained is purified by silica flash chromatography (CH2Cl2-AcOEt gradient: 100-0 to 90-10). 0.86 g of beige solid is isolated (yield: 36%).[0264]TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH: 95-5, Rf=0.71.[0265]F=162 C.[0266]1H NMR (CDCl3) ppm: 3.28 (t, 2H, J=5.18 Hz), 3.44 (s, 3H), 3.67-3.88 (m, 3H), 3.93-4.09 (m, 3H), 6.73 (s, 1H), 7.35 (d, 1H, J=7.6 Hz), 7.54 (t, 1H, J=7.6 Hz), 7.62 (t, 1H, J=7.6 Hz), 7.73 (d, 1H J=8 Hz).[0267]MS (+ESI) m/z 401 (MH+)

Statistics shows that 3,5-Dichloro-1-methylpyrazin-2(1H)-one is playing an increasingly important role. we look forward to future research findings about 87486-33-7.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Leroy, Isabelle; Dupont-Passelaigue, Elisabeth; Mialhe, Samuel; Junquero, Didier; Valeille, Karine; US2013/40928; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63286-28-2, These common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, 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 3-chloro-2-hydrazinopyrazine (3.0 g, 20.75 mmol), prepared from 2,3-dichloropyrazine and hydrazine using a procedure analogous to that described in the literature (Huynh-Dinh et al, J. Org. Chem. 1979, 44, 1028), was added 8 mL of triethyl orthopropionate. After refluxing for 10 h, the reaction was cooled down to ambient temperature and the precipitate was filtered. The solid was purified by flash chromatography (100% ethyl acetate, then 10% methanol in ethyl acetate) to give 2.73 g of the title compound as a solid. 1H NMR (500 MHz, CDCl3) delta 1.54 (t, 3H, J=7.6 Hz), 3.16 (q, 2H, J=7.8 Hz), 7.70 (d, 1H, J=4.5 Hz), 7.83 (d, 1H, J=4.8 Hz)

Statistics shows that 2-Chloro-3-hydrazinylpyrazine is playing an increasingly important role. we look forward to future research findings about 63286-28-2.

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 54608-52-5, 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. 54608-52-5, name is 2-Hydrazinopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To 2-hydrazinopyrazine (2 g, 18.16 mmol) was added isonicotinic acid (pyridine-4- carboxylic acid, 4.47 g, 36.3 mmol, commercially available e.g. from Sigma-Aldrich or Allichem LLC) followed by polyphosphoric acid (50 mL), and the reaction was stirred at 155 0C for 18 hours. The hot solution was added to ice and neutralised by addition of ammonia 0.88. The aqueous solution was then extracted with ethyl acetate (3 extractions), washed with brine, and dried. The yellow solid thus obtained was treated with Dichloromethane, and any remaining solid material was filtered off and put to one side. The filtrate was evaporated and the residue was purified by chromatography using 0-10% of methanol in Dichloromethane as eluent. The fractions containing the product were evaporated to give ~260mg of yellow solid which was combined with the material set aside earlier to give 0.538 g of 3-(4- pyridinyl)[1 ,2,4]triazolo[4,3-a]pyrazine. LCMS: [M+H]+ = 198 retention time = 0.35 minutes (2 minute method)

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

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 2727-13-1, 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. 2727-13-1, name is 3-Amino-6-chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

DIPEA (200 muIota, 1.15 mmol) was added to a solution of 3-amino-6-chloropyrazine-2- carboxylic acid (50 mg, 0.29 mmol), 2-(aminomethyl)-1-ethyl-6-methoxy-3-methyl-1H-1 ,3- benzodiazol-3-ium iodide, Intermediate 13 (100 mg, 0.29 mmol) and HBTU (142 mg, 0.37 mmol) in anhydrous DMF (1 ml). The resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated under a flow of nitrogen to afford the crude product as an oil. The crude material was purified by flash column chromatography on C18 (12 g). The column was eluted with MeCN:H20 + 0.1 % formic acid using the following gradient (%MeCN, column volumes): 10%, 2 CV; 10-100%, 20 CV; 100%, 2 CV. The desired fractions were combined and lyophilised to yield the product as an off-white solid (84 mg, 58%).1H NMR (250 MHz, DMSO-de) delta 9.57 (t, J = 5.3 Hz, 1 H), 8.38 (s, 1 H), 7.93 (d, J = 9.1 Hz, 1 H), 7.66 (s, 2H), 7.57 (d, J = 2.2 Hz, 1 H), 7.29 (dd, J = 9.1 , 2.3 Hz, 1 H), 4.99 (d, J = 5.3 Hz, 2H), 4.62 (q, J = 7.0 Hz, 2H), 4.09 (s, 3H), 3.91 (s, 3H), 1.38 (t, J = 7.1 Hz, 3H). LC/MS (System C): m/z (ESI+) = 375 [M(35CI)+], 377 [M(37CI)+]), R = 1.83 min, UV purity = 100%.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-6-chloropyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 136927-64-5

The mixture of 1-chloropyrrolo[1,2-a]pyrazine (200 mg, 1.31 mmol) and pivalohy-drazide (346.47 mg, 2.62 mmol) in MeCN (20 mL) was stirred at 80 C. for 24 h. The solvent was removed to give the crude product, the crude product was purified by FCC (petroleum ether/ethyl acetate=100:0 to 70:30).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 136927-64-5.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 723286-68-8, The chemical industry reduces the impact on the environment during synthesis 723286-68-8, name is Ethyl 5,6,7,8-Tetrahydro-1,2,4-triazolo[4,3-a]pyrazine-3-carboxylate, I believe this compound will play a more active role in future production and life.

Example 240: Preparation of 7-[(S)-4-(2,3-dihydro-[l,4]dioxino[2,3-b]pyridin-3-yl)- benzyl]-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyrazine-3-carboxylic acid ethyl ester (240) A solution of Intermediates C (4.88 g, 20.0 mmol) and X (4.76 g, 24.3 mmol) in dry DCE (145 mL) is stirred for 20 min. Sodium triacetoxyborohydride (8.58 g, 40.5 mmol) is added, and the reaction is stirred at rt overnight. The mixture is diluted with DCM and washed with sat. NaHCC>3 and brine, dried over Na2S04, filtered and concentrated. The residue is purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford the title product 240. (LC/MS method 16: ES+ m/z 422.3 [M+H]+, Rt = 2.81 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, Ethyl 5,6,7,8-Tetrahydro-1,2,4-triazolo[4,3-a]pyrazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRUNETTE, Steven, Richard; ABEYWARDANE, Asitha; BURKE, Michael, J.; KAPADIA, Suresh, R.; KIRRANE, Thomas, Martin, Jr.; NETHERTON, Matthew, Russell; RAZAVI, Hossein; RODRIGUEZ, Sonia; SAHA, Anjan; SIBLEY, Robert; SMITH KEENAN, Lana, Louise; TAKAHASHI, Hidenori; TURNER, Michael, Robert; WU, Jiang-Ping; YOUNG, Erick, Richard, Roush; ZHANG, Qiang; ZHANG, Qing; ZINDELL, Renee, M.; WO2013/134226; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1111638-10-8,Some common heterocyclic compound, 1111638-10-8, name is 3-Chloro-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4ClN3, 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 3-chloro-5H-pyrrolo[2,3-]pyrazine (1.00 g, 6.51 mmol) in DMF (33 mL) was added N-bromosuccinimide (1.159 g, 6.51 mmol). The reaction mixture was stirred at room temperature for 18 h. At completion, the reaction was concentrated and the resulting residue was treated with water (30 mL). The resulting slurry was stirred for 30 min, then filtered and washed with water (20 mL). The precipitate was dried for 3 h under vacuum at 70 C to afford crude 7-bromo-3-chloro-5H-pyrrolo[2,3-]pyrazine as brown solid (1.136 g, 48% yield). LCMS: m/z 232 (M+H)+, Rt= 0.80 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5H-pyrrolo[2,3-b]pyrazine, its application will become more common.

Reference:
Patent; NOVARTIS AG; BAGDANOFF, Jeffrey T.; CHEN, Zhuoliang; DORE, Michael; FORTANET, Jorge Garcia; KATO, Misunori; LAMARCHE, Matthew J.; SARVER, Patrick James; SHULTZ, Michael; SMITH, Troy Douglas; WILLIAMS, Sarah; (156 pag.)WO2016/203404; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

15707-23-0, name is 2-Ethyl-3-methylpyrazine, 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. Safety of 2-Ethyl-3-methylpyrazine

In an air atmosphere, a nitrogen-containing heterocyclic compound 2e (13.2 mg, 0.1 mmol),Pentamethylcyclopentadienyl iridium (III) chloride dimer (2.0mg), Bistrifluoromethanesulfonimide silver salt (5.8mg), Lithium carbonate (14.8mg) and silver acetate (33.4mg),Use a syringe to inject a 1,2-dichloroethane solution (1.0 mL) containing the alkyne compound 3c (85.6 mg, 0.2 mmol) into the reactor and place the reaction at 120 C for 24 hours.The end of the reaction was determined by thin layer chromatography,The reaction solution was filtered through diatomaceous earth, and then concentrated by spinning with 400 mesh silica gel to prepare a dry powder.The reaction product was separated by column chromatography, 5 g of 400 mesh silica gel,The developing agent is a petroleum ether and ethyl acetate with a volume ratio of 100: 1 to 20: 1 to obtain an alkynyl-containing nitrogen-containing heterocyclic derivative 2-methyl-3-(4-(triisopropylsilyl)-3-butyn-1-yl)pyrazine (1e), 22.0 mg, purity 95%, yield 73%

The synthetic route of 15707-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong University of Technology; Li Xianwei; Rao Jianxing; (22 pag.)CN110256480; (2019); 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 109838-85-9 as follows. Product Details of 109838-85-9

(a) (2R,5R)-2-[(Chloromethyl-dimethyl-silanyl)-methyl]-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine To a solution of (R)-2-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine (7.0 g, 38 mmol), bis(chloromethyl)dimethylsilane (6.0 g, 38 mmol) in THF (150 mL) was added n-butyl-lithium (20 mL, 50 mmol) at -65 to -75° C. dropwise. The mixture was allowed to gradually warm to RT overnight. An ammonium chloride solution at 0° C. was added and the reaction mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, concentrated, and purified by silica gel chromatography (2percent EtOAc in petroleum ether) to give the title intermediate (5 g, 44percent yield) as a clear oil 1H NMR: (MeOD, 400 MHz) delta(ppm): 4.15 (m, 1H), 3.99 (m, 1H), 3.72 (m, 6H), 2.95 (m, 2H), 2.30 (m, 1H), 1.45 (m, 1H), 1.08 (m, 4H), 0.75 (m, 3H), 0.26 (s, 6H).

According to the analysis of related databases, 109838-85-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; McKinnell, Robert Murray; Long, Daniel D.; US2013/287731; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem