Month: April 2021

Related Products of 78342-42-4, 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. 78342-42-4, name is (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3,42 g (18.5 mmol) of commercially available (2S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine in 100 mL of tetrahydrofuran at -70 ¡ãC was added 12 mL (19 mmol) of a1.6M solution of butyllithium in hexanes. After stirring at this temperature for 20 min, 5 g (22.3 mmol)of 2,4,5-trifluorobenzyl bromide in 20 mL of tetrahydrofuran was added and stirring was continued for 3h before warming the reaction to ambient temperature. The reaction was quenched with water,concentrated in vacuo, and extracted with ethyl acetate. The combined organic phase was washed with brine, dried, and concentrated in vacuo. Purification by flash chromatography (silica gel, 0-5percent ethylacetate in hexanes) afforded the title compound.IHNMR (500 MHz, CDCls): 8 7.01 (m, 1H), 6.85 (m, 1H), 4.22 (m, 1H), 3.78 (m, 3H), 3.64 (m, 3H),3.61 (m, 1H), 3.20 (m, 1H), 2.98 (m, 1H), 2.20 (m, 1H), 0.99 (d, 3H, J = 8 Hz), 0.62 (d, 3H, J = 8 Hz).

The chemical industry reduces the impact on the environment during synthesis (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/23750; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, molecular formula is C6H7N3O2, 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. Product Details of 16298-03-6

Step 1 : Methyl 3-(4-fluorobenzamido)pyrazine-2-carboxylate[0164] To a solution of methyl 3-aminopyrazine-2-carboxylate (1.53 g, 10 mmol) in pyridine (50 mL), is added 4-fluorobenzoyl chloride (1.58g, 10 mmol). After 2 h at 70 C, the reaction mixture is cooled to rt, and the pyridine is removed by rotary evaporation. The crude residue is taken up in saturated sodium bicarbonate solution and extracted with DCM. Purification by silica gel chromatography (gradient: 25percent EtOAc/Hexane to 100percent EtOAc) gave methyl 3-(4- fluorobenzamido)pyrazine-2-carboxylate (0.8 g) as a white solid. 1H NMR (400 MHz, DMSO-d6) d 11.42 (s, IH), 8.71 (d, IH), 8.55 (d, IH), 8.08 (m, 2H), 7.38 (m, 2H), 3.73 (s, 3H). LCMS: 276 (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 16298-03-6, its application will become more common.

Reference:
Patent; KALYPSYS, INC.; SMITH, Nicholas, D.; PAYNE, Joseph, E.; HOFFMAN, Timothy, Z.; WO2010/14739; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 186534-02-1, The chemical industry reduces the impact on the environment during synthesis 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, I believe this compound will play a more active role in future production and life.

In 10 mL of methanol was dissolved 2,4-dimethylphenylhydrazide hydrochloride (1.72 g, 10 mmol). To the solution, 3,5,6-trimethylpyrazine-2-carbaldehyde (1.50 g, 12 mmol) was added with an ice-bath under the protection of N2. After the mixture was stirred for 10 min, a lot of brick red precipitate showed and the reaction was then complete. The mixture was filtered through a suction funnel, and the brick red solid was transferred to a vacuum oven to be dried for using directly in the next reaction step of the reaction. The red brick intermediate (3.04 g, 10 mmol) was dissolved in 25 mL of methanol, and 1.68 ml of anhydrous triethylamine and 1.7 ml of trifluoroacetic anhydride were added respectively with an ice-bath under the protection of N2, and the reaction was run for 30 minutes. The reaction was monitored by TLC till completion. The resulting material was extracted with Ethyl acetate, dried over anhydrous Na2SO4, separated by a silica gel column (ethyl acetate:petroleum ether=1: 3) to get T-006 as a light yellow solid (3.25 g, 89.3%). ESI-MS: [M+H]+ m/z 365.1. 1H-NMR (CDCl3, 300 MHz) delta: 2.1 (s, 3H), 2.42 (s, 3H), 2.46 (s, 3H), 2.54 (s, 3H), 2.85 (s, 3H), 7.08 (d, j=7.05 Hz, 1H), 7.24 (d, J=7.21 Hz, 1H), 7.25 (s, 1H), 7.55 (s, 1H); Anal. (C18H19F3N4O) C, H, C; found C, 59.44%, H, 5.319%, N, 15.23%; requires: C, 59.33%, H, 5.26%, N, 15.38%.

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, 3,5,6-Trimethylpyrazine-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GUANGZHOU MAGPIE PHARMACEUTICALS CO., LTD.; Wang, Yuqiang; Chen, Haiyun; Zhang, Zaijun; Zhang, Gaoxiao; Yu, Pei; Sun, Yewei; Shan, Luchen; Tao, Liang; (20 pag.)US2019/218192; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 22047-25-2, A common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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.

A stirred solution of 1-(pyrazin-2-yl)ethanone (1.24 g, 0.01 mol) in methanol (20 ml) was added dropwise to a solution of 4-chloro-6-hydrazinylpyrimidine (1.44 g,0.01 mol) in methanol (30 ml) plus three drops of glacial acetic acid. The mixture was refluxed for 4 h and then cooled to room temperature. The precipitated solid was filtered off and washed with cold methanol to obtain a white solid. Yield: 86.3 %. 1H NMR (400 MHz, DMSO) d ppm: 11.16 (s, 1H), 8.62-8.53 (m, 5H), 9.46 (s, 1H), 7.48(s, 1H), 2.40 (s, 3H). (Fig. S1). 13C NMR (100 MHz,DMSO) dppm: 162.94, 159.80, 158.21, 150.26, 148.14,143.83, 143.13, 142.63, 102.99, 11.91. (Fig. S2). ESI-MS (DMF, positive ion mode): m/z = 249.07([M + H]+), C10H9ClN6 theoretical mass: 248. (Fig. S3). IR/cm-1(KBr):1565 (s), 1369 (m), 3150 (m), 3438 (m).

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:
Article; Hasi, Qi-Meige; Fan, Yan; Feng, Xiao-Xia; Yao, Xiao-Qiang; Liu, Jia-Cheng; Transition Metal Chemistry; vol. 41; 6; (2016); p. 685 – 692;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 4774-14-5, name is 2,6-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. Formula: C4H2Cl2N2

STAGE 1: 2,6-Diiodopyrazine is prepared from 2,6-dichloropyrazine by the method of Example 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4774-14-5, its application will become more common.

Reference:
Patent; Imperial Chemical Industries, PLC; US4975112; (1990); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

889447-19-2, name is 2-Chloro-5H-pyrrolo[2,3-b]pyrazine, 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. name: 2-Chloro-5H-pyrrolo[2,3-b]pyrazine

To a solution of 2-chloro-5H-pyrrolo[2,3-b]pyrazine (80 mg, 1.82 mmol) in2-methyltetrahydrofuran (10 mL) was added NIS (451 mg, 2.00 mmol), and the reaction mixturewas stirred at rt overnight. Saturated aqueous sodium thiosulfate (50 mL) was added to quenchthe reaction, and the resulting mixture was partitioned. The aqueous layer was extracted withEtOAc (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL),dried over anhydrous Na2S04, filtered, and the filtrate was concentrated in vacuo. The residuewas purified by silica gel chromatograph (PE/EtOAc (v/v) = 20/1-4/1) to give the title compoundas a yellow solid ( 456 mg, 89 % ).MS (ESI, pos. ion) m/z: 280.00 [M+Ht;1H NMR (600 MHz, DMSO-d6) 8 (ppm): 12.81 (s, lH), 8.36 (s, lH), 8.21 (d, J = 2.7 Hz, lH).

The synthetic route of 889447-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 486424-37-7,Some common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, molecular formula is C5H4BrN3O2, 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.

CDI (2.23 g, 13.8 mmol) was added to a suspension of commercial 3-amino-6- bromopyrazine-2-carboxylic acid (2.00 g, 9.17 mmol) in DMF (20 ml). The reaction was stirred at RT for 16 h. The reaction mixture was cooled (0 C) then diluted with water (20 ml). The solid was collected by filtration then washed with the minimum volume of water and cooled (0 C) MeCN then dried under vacuum to afford the product as a yellow solid (2.23 g, 86%). 1H NMR (250 MHz, DMSO-cfe) delta 8.55 (s, 2H), 7.96 – 7.82 (m, 3H), 7.15 – 7.07 (dm, 1 H). LC/MS (System A, MeOH quench): m/z (ESI+) = 232 [Methyl ester M(79Br)H+], 234 [Methyl ester M(81Br)H+]), Rt = 0.87 min, UV purity = 95%.

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

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

Related Products of 143591-61-1, The chemical industry reduces the impact on the environment during synthesis 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Method B 3-Bromo-?/-(3′-(trifluoromethyl)phenyl)imidazori,2-alpyrazin-8-amine [00247] Sodium hydride (84 mg, 2.10 mmol – 60% in mineral oil) was dissolved in DMSO (2mL). 3-(Trifluoromethyl)aniline (340 mg, 0.263 mL, 2.11 mmol) was then added and the resulting mixture was stirred at room temperature under a nitrogen gas atmosphere for 10 minutes. A solution of 3-bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (245 mg, 1.05 mmol) in DMSO (2 mL) was then added and stirring at room temperature under a nitrogen gas atmosphere continued for another 2 hours. The reaction was quenched by the addition of saturated ammonium chloride solution (aq.) followed by extraction into EtOAc. The organic extracts were washed with brine, dried and concentrated in vacuo. Purification by flash column chromatography (gradient 7:1 to 6:1 40-60 petrol :EtO Ac) followed by trituration with 40-60 petrol gave the title compound (98 mg, 26%) as a white powder. 1H NMR (d6- DMSO): 10.12 (IH, s), 8.58 (IH, br s), 8.32 (IH, d, J 8.5 Hz), 7.88 (IH, d, J4.6), 7.85 (IH, s), 7.63 (IH, d, J4.7), 7.56 (IH, t, J7.9), 7.35 (IH, d, J7.8).

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-Bromo-8-chloroimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 2-aminomethyl-3-chloropyrazine hydrochloride (content 76%, 69.4 mmol, 16.43 g), cis-4- hydroxycyclohexanecarboxylic acid (69.4 mmol, 10 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (104 mmol, 19.95 g), 4-dimethylaminopyridine (6.94 mmol, 0.847 g) in dichloromethane (200 ml) was added N,N-diisopropylethylamine (173 mmol, 30.3 ml, 22.41 g) until pH became eight and the reaction mixture was stirred at room temperature for 18 hours. Then it was concentrated in vacuo, ethyl acetate and water were added and the organic layer separated. The water layer was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried (MgSC ) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient of 0% to 7% methanol). All fractions that contained product were combined and concentrated in vacuo. The residue was dissolved in dichloromethane (400 ml) and washed with 2 M sodium hydroxide (aq) (three times 100 ml), washed with brine, dried (MgSC ) and concentrated in vacuo to give (cis)-N-((3- chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (15.47 g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chloropyrazin-2-yl)methanamine hydrochloride, its application will become more common.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5049-61-6,Some common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, molecular formula is C4H5N3, 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.

Initial attempt showed that the reaction gave a lot of black polymers after a few min., with the main product being 3,5-dichloro-2-amino pyrazine. Only small amount of 5- chloro-2-aminopyrazine was isolated (eq 7). This reaction could not be scaled up because it was not reproducible.

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

Reference:
Patent; THE GOVERNMENT OF THE UNITED STATES, as represented by the secretary of HEALTH AND HUMAN SERVICES; WO2007/124345; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem