Tag: M.W=300-400

Some common heterocyclic compound, 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate, molecular formula is C9H7Br2N3O2, 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. SDS of cas: 87597-21-5

Step B: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2-yl)methanolTo a stirred solution of ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxyiate (13.95 g, 40mmol) 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: 1 H-NMR (300 MHz, d6-DMSO): delta =8.93 (s, 1 H), 8.05 (s, 1 H), 5.46 (bs, 1 H), 4.63 (s, 2H) ppm. UPLC-MS: RT = 0.73 min; m/z 308.0 [MH+]; required MW = 307.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87597-21-5, its application will become more common.

243472-70-0, name is 5-Bromo-2,3-diphenylpyrazine, 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. Formula: C16H11BrN2

[00130] To 50 g (0.161 mol) of 5-bromo-2,3-diphenylpyrazine, 116 g (0.884 mol, 5.5 eq/mol) of 4-(isopropylamino)-butan-l-ol and 13.33 g of KI (0.080 mol, 0.5 Eq/mol) were added. The reaction mixture was stirred, warmed and then heated up to 140C for about 18- 20 hrs. The reaction was monitored by TLC up to completion (starting material about 1% by TLC). The reaction mixture was cooled down to room temperature. After the reaction was completed, the following work up step was performed: (0208) [00131] Option 1 : Ethyl acetate was added (500 mL, 10 vol) and the organic phase was washed with water (150 mL, 3 vol). The organic phase was separated and aqueous phase was extracted with ethyl acetate (150 mL, 3 vol). The organic phases were joined and washed with water (200 mL, 2 vol) three times. (0209) [00132] The solvent was distilled off under vacuum at not more than (“NMT”) 40C until 1 vol (oil appearance). (0210) [00133] Option 2: The material (mixture) was dissolved in acetone (250 mL, 5 vol), the solution obtained was cooled down to 0C to 5C and anti-solvent / water was added (1000 mL, 20 vol) for 40 minutes, then the suspension was stirred for about 30 minutes at about 0C-5C. The solid material was filtered and washed with water (200 mL, 4 vol). Crude wet product was obtained as yellow solid yielding 101.8 % WY (87 % MY), HPLC purity 90.8% on area at this stage. (0211) [00134] The crude material, obtained in either of the above described options, was purified through crystallization from acetone :-heptane as follows: to a solution of 4-((5,6-diphenyl- pyrazin-2-yl)(isopropyl)amino)butan-l-ol crude in acetone (175 mL, 3.5 vol) at 0C – 5C, hexane (600 mL, 12 vol) dropwise in about 120 min was added, then the precipitated mixture was cooled down to about -10C and stirred for about 60 min. The product was filtered off and washed with hexane (250 mL, 5 vol) and dried under vacuum at 25C. Pure product was obtained as yellowish solid yielding overall 77.2%, (66.5% MY), HPLC purity 98.2% on area.

The synthetic route of 243472-70-0 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 1209646-17-2, These common heterocyclic compound, 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)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.

Example 214Step 1: Synthesis of 5′-(3-{ l-r4-(2-Amino-pyrimidin-5-yl)-phenyll-cyclobutyl|- r i,2,41oxadiazol-5-yl)-2,3,5,6-tetrahydro-r i,2’lbipyrazinyl-4-carboxylic acid tert-butyl ester (R81)To a suspension of R80 (490 mg, 1.59 mmol) in dioxane (10 ml) is added CDI (260 mg, 1.59 mmol) at room temperature. The mixture is stirred at 50 C for 30 minutes. After this time 1-2.5 (300 mg, 1.06 mmol) is added and the resulting mixture is heated at 80 C for 18 hours. After this time the reaction appears complete and is cooled and poured into NaHCC”3 (sat.) and EtOAc. The layers are separated and the aqueous phase is extracted with EtOAc (2x). The combined organics are dried (MgS04), filtered and concentrated to give the crude product which is purified via flash chromatography (25g silica gel, 0-8% MeOH/DCM). Product-containing fractions are combined and concentrated to give R81. (210 mg)

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

Synthetic Route of 866327-72-2, 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 866327-72-2 as follows.

A solution of 5-dibromomethyl-pyrazine-2-carboxylic acid methyl ester (1.00 g, 3.23 mmol) in a mixture of ethanol (20 mL) and THF (10 mL) was heated to 80 C. A solution of silver nitrate (2.20 g, 12.9 mmol) in H2O (4 mL) was added. The reaction mixture was heated at 80 C. for 1.25 h and was filtered while hot. The filtrate was concentrated to yield the title compound (1.36 g). This material was carried to the next step without purification.

According to the analysis of related databases, 866327-72-2, the application of this compound in the production field has become more and more popular.

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. 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

Method 19: Synthesis of 5-(5-{(R)-l-Cvclopropyl-l-r5-(3,4,5,6-tetrahvdro-2H- ri,2nbipyrazinyl-5′-yl)-ri,2,41oxadiazol-3-yll-ethyl}-pyridin-2-yl)-pyrimidin-2- ylamine (Example 134) Step 1: Synthesis of 1-25A suspension of 1- 18.3 (209 mg, 0.657 mmol) and CDI (102 mgs, 06328 mmol) in 1,4- dioxane (3 mL) in a sealed tube is stirred at 55 C for one hour. A solution of 1-8.10 (225 mg, 0.598 mmol) in dioxane (3ml) is added and the reaction mixture is stirred at 120 C for 18 hours. After cooling to room temperature, the reaction mixture is poured into brine and extracted with EtOAc (4x20ml). The combined organic fractions are dried with sodium sulfate, filtered, and is concentrated in vacuo. The resdiue is purified by flash chromatography (Si02, Biotage SNAP lOOg, 0-5 MeOH/DCM) to yield 1-25 (298 mg), m/z 649 [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; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John, D.; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40137; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

Step 4: synthesis of 5-[5-(l-{5-[5-(piperazin-l-yl)pyrazin-2-yl]-l,2,4-oxadiazol-3- yl}cyclobutyl)pyridin-2-yl]pyrimidin-2-amine (Example 60).Methanol (10.0 mL) is cooled to -5 C and treated with acetyl chloride (1.00 mL). To this mixture is added R51 (0.50 g, 0.90 mmol) and the resulting mixture is stirred for 16 hours. The resulting mixture is treated with 7N ammonia in methanol until basic by pH paper and concentrated in vacuo. The resulting solid is treated with acetonitrile and diluted with water. The mixture is filtered and the filtrate is treated with saturated NaHC03 (3 mL) and the solid is collected by filtration to afford the title compound (90.00 mg). m/z 457.3 [M+H].

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; DINES, Jonathon, Alan; HUBER, John, D.; LIU, Weimin; LOKE, Pui Leng; MORWICK, Tina, Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40139; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 723286-80-4, A common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H15BrN4O2, 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.

Preparation 154: 3-bromo-5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine To a solution of ie/i-butyl 3-bromo-5,6-dihydro-[1 ,2,4]triazolo[4,3-a]pyrazine- 7(8H)-carboxylate (52 mg, 0.172 mmol) in DCM (6 mL) at 0C was added TFA (0.26 mL). The reaction was stirred at room temperature for 16 hours before concentrating in vacuo. The residue was purified by elution through an SCX-2 column using 2M NHs/MeOH to give the title compound as yellow solid (29 mg, 83%). 1 H NMR (500 MHz, MeOD): delta 4.10 (s, 1 H), 3.93 (t, J = 5.63 Hz, 2H), 3.25 (t, J = 5.63 Hz, 2H). LCMS (ESI) Rt = 0.40 minutes MS m/z 203 [M79Br+H]+

The synthetic route of 723286-80-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4, 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 723286-80-4 as follows.

A mixture of tert-butyl 3-bromo-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate (1.65 mmol, 500 mg), 1-chloro-3-ethynyl-benzene ( 3.3 mmol, 450.5 mg, 0.406 mL), Pd tetrakis (0.083 mmol, 95.3 mg) and sodium acetate (3.3 mmol, 448.9 mg) in DMF anhydrous (10 mL) was stirred at 120C in a MW Biotage Robot 8 oven for 10 minutes, cooled to r.t., poured into water and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the crude residue was purified via automated flash chromatography (Biotage Isolera, SNAP25 cartridge) eluted with Petroleum ether/EtOAc gradient from 30% to 100% of EtOAc. (0197) The title product (280 mg, 47 % yield) was isolated as a pale yellow solid.

According to the analysis of related databases, 723286-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.P.A; GRAZIANI, Davide; RIVA, Carlo; MENEGON, Sergio; TAZZARI, Valerio; (98 pag.)WO2019/145214; (2019); A1;,
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 243472-70-0 as follows. Product Details of 243472-70-0

Add 3-methyl-2-bromo-quinoxaline (622 mg, 2.00 mmol) to cis-5-(isopropylamine) under nitrogen.a solution of methyl-)tetrahydrofuran-2-yl)methanol (1.04 g, 6.00 mmol) in N-methylpyrrolidone (20 mL)After refluxing at 170 C for 15 h, the reaction was monitored by LC-MS, the starting material was completely reacted, and the reaction was cooled and ice water was added to the reaction solution.The ethyl acetate (50 mL*3) was extracted, and the organic mixed phase was washed with water (50 mL) and saturated brine (50 mL*2).Filtration, decompression to solvent, purification by chromatography on silica gel column, and collected under reduced pressure.Drying in vacuo gave 673 mg of Compound VIII as a white solid.

According to the analysis of related databases, 243472-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Yuandong Bio-pharmaceutical Co., Ltd.; Zeng Yanqun; Yan Shengyong; Zhang Tao; Wang Ying; (17 pag.)CN108623541; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1245644-42-1,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.

General procedure: [0199] A suspension of tributyl(R2)stanne (3.11 mmol), 6-bromo-3-iodo-imidazo[1,2-a]pyrazine 17* (3.11 mmol) andPd(PPh3)4 (0.93 mmol) in dioxane (20 mL) was heated to 150 C in a microwave tube for 20 minutes. The resultingmixture was filtered through celite and evaporated under reduced pressure. If necessary, the reaction was then carriedout more times on the same scale. The crude products were combined and purified by flash chromatography to give theintermediate 18*.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-3-iodoimidazo[1,2-a]pyrazine, 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