Tag: M.W=100-200

Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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: 3,5-Dichloropyrazine-2-carbonitrile

11010] To a solution of 3,5-dichloropyrazine-2-carbonitrile(500 mg, 2.87 mmol) in DMF (10 mE) was added (R)-(3-130C-amino)piperidine (690 mg, 3.45 mmol) and then DIEA(1.0 mE, 5.74 mmol) in a dropwise manner. The mixture wasstirred at RT for 90 mm. The mixture was diluted with EtOAc(200 mE), washed with water x2, dried, and concentrated invacuo. The residue was subjected to flash column chromatog-continued raphy with 0 to 25% EtOAc in DCM to isolate (R)-tert-butyl 1 -(6-chloro-5-cyanopyrazin-2-yl)piperidin-3-ylcarbamate (87) (940 mg, 97% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 313339-92-3, its application will become more common.

Reference:
Patent; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 27398-39-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 27398-39-6 name is 3-Chloropyrazine-2-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a suspension of sodium hydride (278 mg, 6.95 mmol, 60percent in oil) in DMF (10 mL) was added 1H-pyrazole (279 mg, 4.11 mmol) at RT and the resulting mixture stirred at room temperature for 30 mins. 3-Chloropyrazine-2-carboxylic acid (500 mg, 3.16 mmol) was added and the mixture heated to 60 oC for 2 h. After cooling to RT, water (20 mL) was added and the mixture extracted with 4.7percent MeOH in DCM (20 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a solid. LRMS m/z (M+H) 191.0 found, 191.0 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloropyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (68 pag.)WO2016/89721; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 16298-03-6,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.

Reference Example 15 3-Iodopyrazine-2-carboxylic acid methyl ester (Reference compound No.15-1) Isoamyl nitrite (5.2 mL, 39 mmol) was added to a suspension of 3-aminopyrazine-2-carboxylic acid methyl ester (1.9 g, 12 mmol) in diiodomethane (20 mL) at 85°C, then the mixture was stirred at 100°C for 15 hours. The reaction mixture was allowed to stand and purified by silica gel column chromatography to give 1.4 g of the title reference compound as a pale yellow solid. (Yield 44percent) 1H-NMR(500MHz,CDCl3) delta 4.04(s,3H),8.47(d,J = 2.1 Hz,1H),8.56(d,J = 2.1 Hz,1H)

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANTEN PHARMACEUTICAL CO., LTD.; EP1602647; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, 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 63286-28-2, Safety of 2-Chloro-3-hydrazinylpyrazine

It was stirred for 4 hours at reflux mixture of the compound obtained in Step 1 (8 g) and triethyl orthoformate (32 mL). The reaction solution was cooled to room temperature, the precipitated solid was washed after filtration, with ethanol, To give the title compound followed by drying under reduced pressure (8.10g, 95%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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

Application of 313339-92-3, The chemical industry reduces the impact on the environment during synthesis 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

11501] Commercial (4aR,8aR)-decahydro-1 ,5-naphthyri- dine (423, 120 mg, 0.86 mmol) was dissolved in 2 mE NMP. To it were added DIEA (150 pL, 0.86 mmol) and then 3,5- dichioropyrazine-2-cabonitrile (150 mg, 0.86 mmol). The mixture was stirred at RT for 1 .5 hour, and to it were added DIEA (450 pL, 2.58 mmol) and dimethylcarbamoyl chloride (240 pL, 2.58 mmol). The mixture was stirred at RT for overnight. It was diluted with 100 mE EtOAc, washed with water x2, dried, concentrated in vacuo, and subjected to silica flash column using 0 to 3% MeOR in DCM to isolate (4aR, 8aR)-5-(6-chioro-5-cyanopyrazin-2-yl)-N,N-dimethyloc- tahydro- 1 ,5-naphthyridine- 1 (2H)-carboxamide (424, 56 mg, 19%). It was mixed with 4-(1 -cyclopentylpiperidin-4-yl) aniline hydrochloride (304) (90 mg, 0.32 mmol), fine-powder cesium carbonate (210 mg, 0.64 mmol), Pd(OAc)2(11 mg, 0.05 mmol), I3INAP (31 mg, 0.05 mmol) in 15 mE dioxane. The mixture was degas sed with nitrogen stream for 3 mM It was then stirred in 115C. bath in nitrogen atmosphere for 1.5 hout The mixture was cooled to RT, diluted with 100 mE EtOAc, and filtered. The filtrate was concentrated in vacuo and subjected to silica flash column using 0 to 11% MeOR in DCM to isolate (4aR,8aR)-5-(5-cyano-6-(4-(1 -cyclopentylpiperidin-4-yl)phenylamino)pyrazin-2-yl)-N,N-dimethy- loctahydro-1 ,5-naphthyridine- 1 (2H)-carboxamide (425). It was dissolved in 10 mE MeOR and 2 mE DM50. To it were added one NaOH solid bead (about 100 mg), Et3N (60 IL) and then 0.5 mE 30% H202. The mixture was stirred at RT for 30 mM, diluted with 10 mE MeCN, stirred for 5 mM, and concentrated, acidified with 0.3 mE TFA, and subjected to reverse phase prep HPEC using 5 mM HC1 (aq) and neat MeCN as mobile phases to isolate (4aR,8aR)-5-(5-carbam- oyl-6-(4-(1 -cyclopentylpiperidin-4-yl)phenylamino)pyrazin-2-yl)-N,N-dimethyloctahydro-1 ,5-naphthyridine-1 (2H)-carboxamide (426) as HC1 salt (23 mg). EC-MS (ESI):mlz (M+1) 575.8. UV: X=269, 276, 305, 335, 372 nm.

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-Dichloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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: C5H7N3

a) 2-Bromo-N-(5-methyl-pyrazin-2-yl)-acetamide To a mixture of 5-methyl-pyrazin-2-ylamine and cesium carbonate (11.2 g) dissolved in dry DMF (30 mL) was added by dropwise addition bromoacetylbromide (2.89 g) and the mixture stirred at rt for 2 hours. Water (200 mL) was added and the mixture extracted with ethyl acetate (2*100 mL) and dried over magnesium sulfate. Concentration of the extract to ~50 mL and addition of isohexane (100 mL) gave the sub-titled compound as a solid (1.64 g). 1H NMR (400 MHz, DMSO-D6) delta 11.06 (1H, s), 9.17 (1H, s), 8.31 (1H, d), 4.16 (2H, s), 2.46 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5521-58-4, its application will become more common.

Reference:
Patent; Bull, Richard James; Skidmore, Elizabeth Anne; Ford, Rhonan Lee; Mather, Andrew Nigel; Mete, Antonio; US2011/172237; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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 1; 5-Isothiocyanatopyrazine-2-carbonitrile; A solution of thiophosgene (1.86 g, 15 mmol) in THF (4 mL) is added dropwise to a solution of 5-aminopyrazine-2-carbonitrile (1.20 g, 10 mmol) and pyridine (2 mL) in CH2CI2 (200 mL) and THF (25 mL) at room temperature. The reaction mixture is stirred at room temperature for 3 h. The mixture is concentrated and the crude product is diluted with ethyl acetate, filtered and concentrated to give the title compound.

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

Reference:
Patent; ELI LILLY AND COMPANY; FAROUZ, Francine, S.; HOLCOMB, Ryan, Coatsworth; KASAR, Ramesh; MYERS, Steven, Scott; WO2010/77758; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 912773-24-1, 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 912773-24-1 as follows.

General procedure: In a 1000ml three-necked flask, equipped with mechanical stirring, Ar gas protection, adding 3-phenyl-6-chloroimidazo [1,2-a] pyrimidine (7.16 g (molecular weight: 229, 0.030 mol), p-bromophenyl boronic acid pinacol ester 9.1 g (molecular weight: 282, 0.032 mol), catalyst Pd (PPh3) 4 was used in an amount of 1.8 g (molecular weight 1154, 0.001556 mol), 120 ml of a sodium carbonate aqueous solution (2M), 300 ml of toluene and 150 ml of ethanol. Stirring reflux, with TLC monitoring reaction, reaction 3.5hs after the reaction is complete. Cooled, separated, evaporated to dryness, using column chromatography The eluent was eluted with 1: 3 ethyl acetate: petroleum ether to give 9.0 g of a pale yellow solid having a purity of 97.0% and a yield of 83.2%. The synthesis step was the same as the fourth step in Example 1,Except that 3-phenyl-6-chloroimidazo[1,2, a]pyrimidine was added Substituted with 6-bromoimidazo [1,2-A]pyrazine,(3-phenylcarbazole-9-yl) -6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b ] Fluorene-2-boronic acid pinacol ester instead of raw materials, other raw materials and process unchanged, Compound 29 was obtained.

According to the analysis of related databases, 912773-24-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gu’an Dingcai Technology Co., Ltd.; Li Yinkui; Tang Jinming; Fan Hongtao; (40 pag.)CN104650089; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 69214-33-1, name is 8-Chloroimidazo[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. Recommanded Product: 69214-33-1

A cooled (0C) suspension of 8-chloroimidazo [1, 2-A] PYRAZINE (18.6 g, 0.12 mol) and sodium acetate (29.8 g, 0.36 mol) in methanol (125 ml, pre-saturated with solid potassium bromide) was treated with bromine (6.5 ml, 0.13 mol) added dropwise over 5 min. After stirring for 10 min thin-layer chromatography indicated no starting material. Solid sodium sulphite (15.3 g, 0.12 mol) was then added to the slurry and stirring continued for 10 min. The mixture was then treated with saturated aqueous sodium hydrogencarbonate (650 ml) added in portions. This mixture was extracted with dichloromethane (2 x 350 ml). The organics were combined, dried over anhydrous magnesium sulphate, filtered and concentrated to afford 3-bromo-8-chloroimidazo [1, 2-A] PYRAZINE as a cream- coloured solid:

The synthetic route of 8-Chloroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/41826; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridine-7- carboxylic acid (1.63 g, 6.93 mmol) in THF (35 mL) was added dropwise (COCl)2 (4.4 g, 34.66 mmol) and 0.1 mL of DMF at 0 C, the mixture was stirred at this temperature for 1 hours and then the solvent was removed. The resulting residue was dissolved in THF (35 mL), (3-chloropyrazin-2-yl)methanamine hydrochloride (1.37 g, 7.63 mmol) and DIEA(2.68 g, 20.79 mmol) was added, the mixture was stirred at 60 C for 1 h. Remove the solvent in vacuo and the residue was extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2S04. The organic layer was concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/THF= 100/20) to afford N-((3-chloropyrazin-2- yl)methyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo [4,3-a]pyridine-7- carboxamide (0.8 g, yield 32%). MS-ESI (m/z): 361 (M+l) + (Acq Method: 10-80AB_2min;Rt: 0.81 min)

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/113942; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem