Tag: M.W=100-200

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

Oxalyl chloride (2.1 mL, 24.0 mmol) was added to a solution of 3-[(l-methylethyl)oxy]-5- [(phenylmethyl)oxy]benzoic acid (5.72 g, 20.0 mmol) in DCM (100 mL) and the mixture stirred at ambient RT for 4 hours. The mixture was evaporated in vacuo to a residue, which was taken up in DCM (25 mL) and added to a stirred mixture of 2-amino-5-methylpyrazine (2.29 g, 21.0 mmol) and pyridine (1.94 mL, 24.0 mmol) in DCM (100 mL) at 50C – 1O0C. The mixture was stirred at RT for 18 hours, the DCM evaporated in vacuo to a residue, which was partitioned between water (50 mL) and ethyl acetate (150 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 30% ethyl acetate in isohexane, and crystallised from ethyl acetate / isohexane to give the desired compound (5.52 g). 1R NuMR delta (CDCl3): 1.3 (d, 6H), 2.5 (s, 3H), 4.5 (m, IH), 5.0 (s, 2H), 6.6 (s, IH), 6.95 (s, IH), 7.0 (s, IH), 7.35 (m, 5H), 8.05 (s, IH), 8.3 (s, IH) and 9.5 (s, IH). m/z 378 (M+H)+.

The synthetic route of 5-Methylpyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-25-1, The chemical industry reduces the impact on the environment during synthesis 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Example 24 5-{[3-(Cyclopropylmethyl)-2,3,4,5-tetrahydro-1 H-3-benzazepin-7-yl]oxy)-N-methyl-2- pyrazinecarboxamide (E24) Step 1: 1,1-Dimethylethyl 7-({5-[(methyloxy)carbonyl]-2-pyrazinyl}oxy)-1,2,4,5- tetrahydro-3H-3-benzazepine-3-carboxylate; 1,1-Dimethylethyl 7-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Description 3 of WO 02/40471) (40 g, 0.15 mole) was dissolved in dry dimethylformamide (200 ml) and treated with sodium hydride (60% in mineral oil, 6.4 g, 0.16 mole). The mixture was stirred at room temperature for 1 hour and then cooled in ice. Methyl 5-chloro- 2-pyrazinecarboxylate (31.2 g, 0.18 mole) was added and the mixture stirred at room temperature for 18 hours. The mixture was poured into ice/water and the resulting solid collected by filtration. This was dissolved in ethyl acetate, dried (sodium sulphate) and evaporated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate/pentane (1:2) to afford the title compound ?H NMR (CDCl3) No. 8.84 (H, s), 8.48 (H, s), 7.18 (H, m), 6.94 (2H, m), 4.01 (3H, s), 3.58 (4H, m), 2.92 (4H, m), 1.49 (9H, s)..

The chemical industry reduces the impact on the environment during synthesis Methyl 5-chloropyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/97778; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 33332-25-1

Step 1Compound (67) (10 g) was suspended in water (35 ml) and 2 mol/L-aqueous solution of sodium hydroxide (34.8 ml) was added and the mixture was stirred at room temperature for 4.5 hours. 2 mol/L-hydrochloric acid (34.8 ml) was added to neutralize and stirred at room temperature overnight. The precipitated insoluble material was collected by filtration, washed with water and dried under reduced pressure to afford Compound (68) (3.47 g).1H-NMR (DMSO-d6) delta 8.93 (1H, s), 9.03 (1H, s).

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, 33332-25-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIONOGI & CO., LTD.; US2012/15961; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3, The chemical industry reduces the impact on the environment during synthesis 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

Into a vessel containing 50 mL ethanol was added 1.0 g of 3-chloropyrazine-2- carbonitrile (Exp-5-g22, 7.2 mmol), 1.1 g PMBNHNH2 (7.3 mmol) and 1.9 g K2C03 (14.2 mmol). The reaction mixture thus provided was heated to reflux and refluxing was continued for 6 hours, then the mixture was cooled to ambient temperature, filtered and the solid was washed sequentially with 10 mL H20 and 10 mL of methanol and dried yielding 1.0 g Exp-5-g23 (calculated yield 56%).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; JONES, Philip; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/63100; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

875781-43-4, These common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]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.

Step 1 To a partial suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g, 25.2 mmol) in 1,4-dioxane (100 mL) was added 2.0 M aqueous NaOH (25 mL, 50.0 mmol) and 37% aqueous formaldehyde (19 mL, 252 mmol). The dark homogenous reaction mixture was stirred at room temperature overnight. The organics were evaporated under reduced pressure. The aqueous layer was neutralized with 1.0 M HCl and extracted with EtOAc (2*). The combined organics were concentrated to afford 2.6 g of an orange solid. Upon standing, a thick brown precipitate formed in the aqueous layer. The precipitate was collected by filtration and dried. The brown solid was extracted with hot 10% MeOH/EtOAC (3*200 mL). The extracts were combined and evaporated to provide an additional 3.05 g of orange solid. Overall yield was 5.65 g (87%) of (2-bromo-7-hydroxymethyl-pyrrolo[2,3-b]pyrazin-5-yl)-methanol.

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 875781-43-4.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, molecular formula is C6H6N2O3, 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. 27825-20-3

EXAMPLE 19 In 5 mL of dimethyl sulfoxide is dissolved 0.42 g of L-alanyl-L-alanine trifluoroacetate. Then, 1.07 mL of triethylamine and 0.71 g of methyl 3-hydroxy-2-pyrazinecarboxylate are successively added to the solution, which is then stirred at 40 C. for 17 hours. The solvent is distilled off under reduced pressure, and 2 mL of water was added to the residue thus obtained. The deposited product is collected by filtration and purified by column chromatography [eluent: chloroform:methanol =30:1) to obtain 0.035 g of (2S)-2-[((2S)-2-{[(3-oxo-3,4-dihydro-2-pyrazinyl)carbonyl]amino}-propanoyl)amino]propanoic acid. IR(KBr) cm-1: 1665, 1675, 1655 NMR(DMSO-d6) delta value: 1.28(3H,d,J=7 Hz), 1.32(3H,d,J=7 Hz), 3.95-4.95(2H,m), 5.1(2H,brs), 7.71(1H,d,J=3 Hz), 7.87(1H,d,J=3 Hz), 8.32(1H,d,J=7 Hz), 9.9(1H,brs)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27825-20-3, its application will become more common.

Reference:
Patent; Furuta, Yousuke; Egawa, Hiroyuki; Nomura, Nobuhiko; US2002/13316; (2002); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

122-05-4,Some common heterocyclic compound, 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, molecular formula is C6H4N2O4, 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.

Pyrazine-2,5-dicarboxylic acid (900 mg, 5.35 mmol) was dissolved in MeOH (9 mL) and Hydrogen chloride ~1.25M solution in Methanol (9 mL) was added. Then the mixture was heated to 50 C and stirred at that temperature for 8 hrs. Then it was left stirring at RT overnight. The day after 2 mL more of HCI ~1.25 M in MeOH was added and the mixture heated to 50 C and stirred at that temperaure for further 1 h. The mixture was cooled down to RT and concentrated under reduced pressure affording 2,5-dimethyl pyrazine-2,5- dicarboxylate (p139, 949 mg, y= 90%). MS (m/z): 197.1 [MH]+.

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

Reference:
Patent; INDIVIOR UK LIMITED; CREMONESI, Susanna; MICHELI, Fabrizio; SEMERARO, Teresa; TARSI, Luca; (364 pag.)WO2016/67043; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6705-33-5, name is Pyrazin-2-ylmethanol, A new synthetic method of this compound is introduced below., 6705-33-5

Step 1: Intermediate 40-a [0220] To a solution of intermediate 29-g (4.62 g, 19.1 mmol) and pyrazin-2-ylmethanol (2.10 g, 19.1 mmol) in THF (38 mL) were sequentially added triphenylphosphine (7.50 g, 28.6 mmol) and DIAD (5.19 ml, 26.7 mmol) at room temperature and the reaction was then stirred at room temperature overnight. Volatiles were removed under reduced pressure. Purification by silica gel chromatography provided intermediate 40-a as a colorless oil.

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; Pharmascience, Inc.; Laurent, Alain; Rose, Yannick; Jaquith, James B.; US2015/191473; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 486460-20-2

3-(Trifluoromethyl)-l,2,4-triazolo[4,3-a] pyrazine (540 mg, 2.87 mmol, from Step A)was hydrogenated under atmospheric hydrogen with 10% Pd/C (200 mg) as a catalyst in ethanol (10 mL)at ambient temperature for 18 h. Filtration through Celite followed by concentration gave a dark coloredoil. Dichloromethane was added to the above oil and the insoluble black precipitate was filtered off.Concentration of the filtrate gave the title compound as an oil.’H NMR (500 MHz, CDC13) 5 2.21 (br, 1H), 3.29 (t, 2H, J = 5.5 Hz), 4.09 (t, 2H, J = 5.5 Hz), 4.24 (s,2H); LC-MS 193 (M+l).

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, 486460-20-2, other downstream synthetic routes, hurry up and to see.

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

A common compound: 19745-07-4, name is 2,5-Dichloropyrazine, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 19745-07-4

Step G: To a solution of (3S)-l-(3,3-dimethylpiperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (0.010 g, 0.026 mmol) in DMF (1 mL) was added 2,5-dichloropyrazine (0.0078 g, 0.052 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.018 mL, 0.10 mmol) and the reaction was stirred for 3 hours at 100 ¡ãC. The reaction was cooled, poured into brine and extracted into EtOAc. The organic layer was washed with water and brine, dried over MgS04, filtered and concentrated under vacuum. Reverse phase HPLC purification of the crude material gave (3S)-l-(l-(5-chloropyrazin-2-yl)-3,3- dimethylpiperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (0.0023 g, 0.0046 mmol, 18percent yield) as a white solid. XH NMR (CDC13, 400 MHz) delta 1.02 (s, 3H), 1.03 (s, 3H), 1.81 – 1.91 (m 1H), 2.12 – 2.21 (m, 1H), 2.71 – 2.81 (m, 2H), 2.95 – 3.05 (m, 2H), 3.03 (m, 3H), 3.52 (dd, 2H), 3.97 (d, 1H), 4.15 – 4.23 (m, 2H), 4.47 – 4.51 (m, 1H), 5.12 (bs, 1H), 6.80 (t, 1H), 7.55 (d, 1H), 7.61 (d, 1H), 7.90 (s, 1H), 8.05 (s, 1H).

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, 19745-07-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem