Tag: M.W=300-400

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 87597-21-5 as follows. Safety of Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate

To a stirred solution of ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate (13.95 g, 40 mmol) in toluene (558 mL) at 0 C. was added 80 mL DIBAH (120 mmol, 3 eq, 1.5M in toluene) dropwise. After stirring overnight at rt, the solution was poured on 1M HCl, extracted with ethyl acetate and the organic phase was washed with water, sole, dried over sodium sulphate and filtered. Removal of the solvent and recrystallyzation from DCM yielded 5.55 g (45.2%) (6,8-dibromoimidazo[1,2-a]pyrazin-2-yl)methanol: 1H-NMR (300 MHz, d6-DMSO): delta=8.93 (s, 1H), 8.05 (s, 1H), 5.46 (bs, 1H), 4.63 (s, 2H) ppm. UPLC-MS: RT=0.73 min; m/z 308.0 [MH+]; required MW=307.0.

According to the analysis of related databases, 87597-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Koppitz, Marcus; Klar, Ulrich; Jautelat, Rolf; Kosemund, Dirk; Bohlmann, Rolf; Bader, Benjamin; Lienau, Philip; Siemeister, Gerhard; US2013/281460; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 243472-70-0,Some common heterocyclic compound, 243472-70-0, name is 5-Bromo-2,3-diphenylpyrazine, molecular formula is C16H11BrN2, 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 mixture of 5- bromo-2,3-diphenylpyrazine (1 g, 3.21 mmol) and 4-(isopropylamino)butan-1 -ol (2.32 g, 17.7 mmol) was added potassium iodide (266 mg, 1 .6 mmol). The mixture was stirred in a pressure vessel at 140C for 2 days. The reaction mixture was cooled to room temp and diluted with water. The mixture was extracted with EtOAc (x4) and the combined organic layers washed with brine, dried over Na2S04, filtered and concentrated. The crude residue was purified with column chromatography eluting with 0-2% MeOH in DCM. The fractions of the desired product were combined, concentrated, and dried under reduced pressure to obtain a brown oil (0.82 g, 71 %). 1 H NMR (400 MHz, Chloroform-d) d 8.02 (s, 1 H), 7.49 – 7.42 (m, 2H), 7.39 – 7.33 (m, 2H), 7.29 – 7.21 (m, 6H), 4.78 (p, J = 6.7 Hz, 1 H), 3.68 (t, J = 6.4 Hz, 2H), 3.43 (dd, J = 9.2, 6.7 Hz, 2H), 1.76 (qd, J = 7.8, 7.1 , 3.9 Hz, 2H), 1.65 (q, J = (0159) 6.8 Hz, 2H), 1.28 (d, J = 6.7 Hz, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2,3-diphenylpyrazine, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; HOLINSTAT, Michael; ADILI, Reheman; WHITE, Andrew; (43 pag.)WO2019/204447; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1209646-17-2, A common heterocyclic compound, 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, molecular formula is C14H20N4O4, 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 suspension of I-77 (3.0 g, 9.71 mmol) in THF (40 ml) is added 1,1?-carbonyldiimidazole (1.6 g, 9.71 mmol) at room temperature. The mixture is stirred at 50 C. for 30 minutes. After this time I-16 (2.5 g, 8.83 mmol) is added and the resulting mixture is heated at 80 C. for 3 hours. The mixture is cooled down and treated with AcOH (8 ml). The mixture is warmed to 80 C. and stirred over night. Upon cooling to room temperature, the reaction is concentrated and diluted with water. The product is extracted into DCM (2×). The combined organics are washed with brine and dried over anhydrous MgSO4. The mixture is filtered and concentrated. The remaining crude is purified via flash chromatography (silica gel, 0-5% MeOH/DCM) to afford I-78 (2.2 g). In a microwave reaction vessel is added I-78 (0.50 g, 0.90 mmol) in 15 ml of DMF, followed by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (0.30 g, 1.35 mmol), tetrakis(triphenylphosphine)palladium(0) (105 mg, 0.09 mmol) and aq. Na2CO3 (2.0M, 1.8 ml). The reaction mixture is stirred at 85 C. for 16 hours. After this time the reaction mixture is poured into brine and extracted with EtOAc (3×). The combined organic fractions are dried over anhydrous MgSO4, filtered, then concentrated in vacuo to give the crude material. Purification via flash chromatography (silica gel, 0-5% MeOH/DCM) affords the title intermediate (150 mg); m/z 570.4 [M+H]

The synthetic route of 1209646-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1209646-17-2,Some common heterocyclic compound, 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, molecular formula is C14H20N4O4, 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 suspension of 1-77 (3.0 g, 9.71 mmol) in THF (40 ml) is added 1,1′- carbonyldiimidazole (1.6 g, 9.71 mmol) at room temperature. The mixture is stirred at 50 C for 30 minutes. After this time 1-16 (2.5 g, 8.83 mmol) is added and the resulting mixture is heated at 80C for 3 hours. The mixture is cooled down and treated with AcOH (8ml). The mixture is warmed to 80C and stirred over night. Upon cooling toroom temperature, the reaction is concentrated and diluted with water. The product is extracted into DCM (2x). The combined organics are washed with brine and dried over anhydrous MgS04. The mixture is filtered and concentrated. The remaining crude is purified via flash chromatography (silica gel, 0-5% MeOH/DCM) to afford 1-78 (2.2 g).

The synthetic route of 1209646-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John; LO, Ho Yin; LOKE, Pui Leng; LIU, Weimin; MORWICK, Tina Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee; WO2012/24150; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4, The chemical industry reduces the impact on the environment during synthesis 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, I believe this compound will play a more active role in future production and life.

The compound obtained in Step 4 (53 mg) was dissolved in chloroform (2 mL), trifluoroacetic acid (0.2 mL) was added and stirred overnight at room temperature. The oil obtained reaction solution by concentration under reduced pressure was dissolved in N, N- dimethylformamide (1.5 mL), Was stirred for 2 hours at 200 C. was added cesium carbonate (111 mg) and 4-fluoro-2- (trifluoromethyl) benzonitrile (64 mg). To the reaction solution was extracted 3 times with ethyl acetate after addition of water, The organic layer was washed with water and saturated brine, Dried and concentrated with sodium sulfate. The resulting residue to give the title compound purified by silica gel column chromatography (19mg, 30%). LRMS (ESI) m / z 372 [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, tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 243472-70-0, A common heterocyclic compound, 243472-70-0, name is 5-Bromo-2,3-diphenylpyrazine, molecular formula is C16H11BrN2, 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.

The reaction flask was charged with 5-bromo-2,3-diphenylpyrazine (100 g, 0.32 mol)4-Isopropylamino-1-butanol (127 g, 0.96 mol) andPotassium iodide (15.9 g, 0.096 mol) was added and the mixture was heated to 150 C for 16 hours.After the system was cooled to room temperature, ethyl acetate (800 mL)Washed with water (800 mL × 2), dried over anhydrous sodium sulfate, filtered,The filtrate was concentrated under reduced pressure and the residue treated with dichloromethane / heptane (1.2 L, v / v = 1: 5)Recrystallization, get4 – ((5,6-diphenylpyrazin-2-yl) – (isopropyl) amino) -1-butanol(75.5 g, yield: 65.3%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Zhang Qianqian; Qu Xiaoxia; (14 pag.)CN107365275; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

58138-79-7, name is 2,6-Diiodopyrazine, 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: C4H2I2N2

1. 2-Iodo-6-allyloxypyrazine This was prepared from 2,6-diiodopyrazine (5.5 g, 16.6 mmol) and allyl alcohol by the procedure described for Example 31 part 1. Chromatography through silica gel using dichloromethane as eluant gave the pure product (2 g), delta (250 MHz, CDCl3) 4.83-4.86 (2H, m, CH2 O); 5.29-5.35 (1H, m, cis-vinyl-H); 5.39-5.48 (1H, m, trans-vinyl-H); 5.98-6.13 (1H, m, vinyl-H); 8.16 (1H, s, pyrazine-H); 8.40 (1H, s, pyrazine-H).

The synthetic route of 58138-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US5260293; (1993); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 87597-21-5, 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 87597-21-5 as follows.

Preparation of Intermediate I-36. Intermediate I-07 (0.50 g, 1.40 mmol) was suspended in DCE (8 mL) and piperidine (0.18 mL, 1.7 mmol) was added dropwise. The reaction mixture was heated at 60 C. for 16 h. Additional piperidine (0.05 mL) was added and heating continued for 2 h. The suspension at RT was filtered affording a solid (impurities) and the filtrate that was concentrated. The resulting residue was triturated with Et2O to render another solid (impurities) and the filtrate that was concentrated to afford the required intermediate I-36 as light orange solid (400 mg, Y: 80%).

According to the analysis of related databases, 87597-21-5, the application of this compound in the production field has become more and more popular.

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

Synthetic Route of 1245644-42-1, A common heterocyclic compound, 1245644-42-1, name is 6-Bromo-3-iodoimidazo[1,2-a]pyrazine, molecular formula is C6H3BrIN3, 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.

Step 1 : To a solution of 6-bromo-3-iodoimidazo[l ,2-a]pyrazine (3.00 g, 9.26 mmol) in DMF (20 mL), was added Na2C03 (2.46 g, 23.2 mmol), 4-chlorophenylboronic acid (1.60 g, 10.2 mmol) and Pd(PPh3)4 (214 mg, 0.18 mmol). The resulting mixture was stirred at 80 C for 18 h under inert atmosphere and was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent Hex/EtOAc 3:2) to afford 6-bromo-3- (4-chlorophenyl)imidazo[l,2-a]pyrazine (930 mg, 32%) as a yellow solid. 1H NMR (400 MHz, CDC13) delta 9.03 (d, J= 1.2 Hz, 1H), 8.36 (d, J= 1.2 Hz, 1H), 7.91 (s, 1H), 7.54 (q, J =12.3 Hz, 4H); MS (ESI) m/z 308 [C13H7BrN4 + H]+.

The synthetic route of 1245644-42-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1245644-42-1, name is 6-Bromo-3-iodoimidazo[1,2-a]pyrazine, molecular formula is C6H3BrIN3, 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. Recommanded Product: 6-Bromo-3-iodoimidazo[1,2-a]pyrazine

General procedure: 6-Bromo-3-thiophen-2-yl-imidazo[1,2- a]pyrazine 18*c Note: An additional 1 mol% of Palladium Acetate and triphenylphosphine was added after 12 hours to increase the yield of the reaction. 1H-NMR (400 MHz, CDCl3): delta = 8.94 (s, 1 H), 8.49 (s, 1 H), 7.95 (s, 1 H), 7.55 (d, J =5.2Hz, 1 H), 7.38 (d, J =3.2Hz, 1 H), 7.27 (s, 1H). Yield: 42.3%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1245644-42-1, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem