Category: 153800-11-4

Related Products of 153800-11-4, 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. 153800-11-4 name is 2-Ethynylpyrazine, 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 stirred solution of alkyne precursor 8b-16b (1.2 equiv) in THF was added dropwise a 1.0 M solution of TBAF in THF (1.44 equiv). The reaction mixture was stirred at room temperature for about 15 min. TLC analysis showed complete conversion of starting material to a major product (the de-silylation intermediate was slightly more polar than the alkyne precursor). The glycosyl azide (1.0 equiv), and 1:1 tert-butyl alcohol-water were then added to the above solution. A solution of sodium ascorbate (0.4 equiv) in water, followed by CuSO4 (0.2 equiv) in water, was successively added. The bright-yellow suspension was stirred vigorously at room temperature overnight. TLC analysis showed complete conversion of the starting material to a major product. The mixture was evaporated under reduced pressure, and the resultant residue was purified by flash chromatography to yield pure material.

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

Reference:
Article; Li, Tiehai; Guo, Lina; Zhang, Yan; Wang, Jiajia; Li, Zhonghua; Lin, Lin; Zhang, Zhenxing; Li, Lei; Lin, Jianping; Zhao, Wei; Li, Jing; Wang, Peng George; Carbohydrate Research; vol. 346; 9; (2011); p. 1083 – 1092;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 153800-11-4, 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 153800-11-4 as follows.

(+)-((2R,3R,4S,5R,6S)-3-Acetoxy-6-(((3R,4R,5S)-5-azido-4-hydroxytetrahydro- 2//-pyran-3-yl)thio)-5-methoxy-4-(4-(3,4,5-trifluorophenyl)-li/-l,2,3-triazol-l- yl)tetrahydro-2 /-pyran-2-yl)methyl acetate (62 mg, 0.101 rnmol) and 2-ethynylpyrazine (16.75 mg, 0.161 mmol) were dissolved in a previously degassed solution of DMF (3 mL) and water (1.000 ml) and the mixture was placed under argon. Sodium ascorbate (23.90 mg, 0.121 mmol) and copper(II) sulfate pentahydrate (35.2 mg, 0.141 mmol) (predissolved in 0.5 rnL water) were added and the reaction mixture was stirred at room temperature for 14 h. The mixture and the solid clinging to the stir bar were dissolved by the addition of dichloromethane and methanol. Water (10 mL) and saturated aqueous sodium bicarbonate (10 mL) were added resulting in the formation of a precipitate. The mixture was filtered through a pad of Celite and the filter cake was rinsed with 5% methanol in dichoromethane. The filtrate was transferred to a separatory funnel . Brine (1(3 mL) was added and the aqueous layer was extracted (with gentle shaking) with 5% methanol in dichloromethane (4 x 15 mL). The combined organic layers were washed with brine (15 mL). The organic layer was dried over MgS04, filtered, and concentrated. The product was purified by column chromatography on silica gel (30% ethyl acetate containing 5% methanol/ hexanes 100% ethyl acetate containing 5% methanol/hexanes; 24 g column) to afford ((2R,3R,4S,5R,6S)-3-acetoxy-6-(((3R,4R,5S)-4-hydroxy-5-(4-(pyrazin-2-yl)-l /7-l ,2,3-triazol-l-yl)tetrahydro-2i7-pyran-3-yl)thio)-5- methoxy-4-(4~(3,4,5-trifluorophenyl)-li/-L2,3~triazoi-l-yl)tetrahydro-2/f-pyran~2- yl)m ethyl acetate (65 mg, (3 09(3 mmol, 90% yield) as a white solid. 41 NMR (4(30 MHz, CHLOROFORMS) d 9.44 (d, 7=0.8 Hz, 1H), 8.55 (s, 2H), 8.35 (s, 1H), 7.83 (s, 1H), 7.47 (dd, .7=8.0, 6 5 Hz, 2H), 5.51 (d, 7=2.8 Hz, H I ), 4.74 – 4.64 (m, 2H), 4 62 – 4 52 (m, 1H), 4.40 (dd, 7=11.5, 5.0 Hz, 1H), 4.32 (dd, 7=11.8, 5.0 Hz, 1 1 1). 4.26 (t, 7=9.9 Hz, 1H), 4.20 – 4.09 (m, 4H), 4 09 – 4 03 (m, 1 H), 3.52 (t, 7=1 1.9 Hz, 1H), 3 36 (s, 3H), 3 17 (ddd. 7=1 1 .8, 9.8, 5.0 Hz, i l l ), 2.1(3 (s, 31 1 ), 1.94 (s, 3H); 1.C7MS (ESI) mie 721 .2 [(M+H)+, calcd for CsoHxrFsNsOgS 721.2], /R = 1.88 min (Method 2).

According to the analysis of related databases, 153800-11-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; XU, Li; YOON, David S.; REGUEIRO-REN, Alicia; JALAGAM, Prasada Rao; PANDA, Manoranjan; NAIR, Satheesh Kesavan; (171 pag.)WO2019/241461; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 153800-11-4, name is 2-Ethynylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 153800-11-4

A reaction flask was charged with (2R,4S,4aS)-9,10-difluoro-8-iodo-2,4-dimethyl-2,4,4a,6- tetrahydro-lH,leta-spiro[[l,4]oxazino[4,3-a]quinoline-5,5′-pyrimidine]-2′,4′,6′(3eta)-trione(Intermediate 89(b), 350 mg, 0.71 mmol), copper(I) iodide (6.78 mg, 0.04 mmol) and dichlorobis(triphenylphosphne)palladium (II) (25.01 mg, 0.04 mmol) in acetonitrile (3 ml) underN2. The flask was degassed and backfilled 3 times with a balloon containing a 50:50 mixture ofArgon/H2. TEA (0.794 ml, 5.70 mmol), which had been degassed by bubbling Ar through for 20 minutes, was added. A solution of 2-ethynylpyrazine (119 mg, 1.14 mmol) in 1 ml CH3CN that had been degassed by bubbling Ar through for 5 minutes, was added. The reaction mixture was heated to 90 0C (external temperature) under the N2/H2 balloon atmosphere for 45 minutes. The mixture was diluted with EtOAc and washed with water and brine. The combined aqueous layers were twice more extracted with EtOAc, which was washed with brine. The combined EtOAc extracts were dried and concentrated, and the residue was chromatographed on silica gel (100%CH2Cl2, followed by gradient elution to 100% EtOAc), to afford the title product as a yellow solid.MS (MH+): 468 for C23Hi9F2N5O41H NMR (300MHz, DMSO-d6) delta: 0.9 (d, 3H), 1.1 (d, 3H), 2.9 (d, IH), 3.1 (m, IH), 3.5 (d, IH),3.7-3.8 (m, IH), 3.9 (m, IH), 4.1 (d, IH), 7.1 (d, IH), 8.6 (s, IH), 8.7 (s, IH), 8.8 (s, IH), 11.6 (s,IH), 11.9 (s, IH).

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 153800-11-4.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/4382; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 153800-11-4, name is 2-Ethynylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H4N2

Preparation 172:2-(4-Amino-3-bromo-5-pyrazin-2-ylethinyl-phenyl)-4-methyl-l,3-thiazole-5-carbo xylic acid ethyl ester; [1397] 2-(4- Amino-3-bromo-5-iodo-phenyl)-4-methyl- 1 ,3-thiazole-5-carboxylic acid ethyl ester (0.5g, lmmol) obtained in Preparation 171, dichlorobis(triphenylphosphine)palladium (37mg, 0.05mmol), cupper iodide (lOmg, 0.05mmol), 2-ethinylpyrazine (220mg, 2.0mmol) and triethylamine (4.47mL, 5mmol) were added to 5mL of tetrahydrofuran, and the mixture was reacted for 12 h at room temperature. After reaction, the solution was filtered through celite using 3OmL of ethyl acetate. After filtration, 2OmL of sodium bicarbonate solution was added, and 1OmL of ethyl acetate was added. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and purified by column chromatography to give the title compound (0.5g, Yield 52%).[1398] NMR: 1H-NMR(DMSO) delta 8.78(1H, s), 8.59(1H, s), 8.53(1H, s), 8.12(1H, s), 8.00(1H, s), 5.19(2H, s), 4.34(2H, q), 2.74(3H, s), 1.36(3H, t)[1399] Mass(EI): 444(M++ 1)

According to the analysis of related databases, 153800-11-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG LIFE SCIENCES LTD.; CHOI, Sung Pil; KIM, Geun Tae; SONG, Jeong Uk; KIM, Tae Hun; LIM, Dong Chul; KANG, Seung Wan; KIM, Hyung Jin; WO2010/93191; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 153800-11-4, These common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, 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 231(100mg, 0.282mmo1) and 10(58.8mg, 0.565mmo1) in 2OmL of Et3N was added Pd(PPh3)2C12 (991mg, 0Oi4mmol) and Cul (538mg, 0O28mmol). The mixture was protected with N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showedcomplete conversion of starting material to a major product. The reaction mixture was then concentrated in vacua The crude product was purified by Prep-HPLC to give the target product Compound 125(23mg, yield: 24.66%).LCMS: in/z 331 (M+HY?H NMR (400 MHz, CDCI3): d 8.83 (d, J:::: 6.4 Hz, 11:1), 862 (s, 11:1), 854 (s, 1H), 793 (d, J:::2.4 Hz, IH), 7.79-7.75 (m, 2H), 735-733 (m, 2H), 6.79 (d, J= 2.4 Hz, 1H).

The synthetic route of 153800-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 153800-11-4, These common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, 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 235(100mg, 0.272mrno1) and 10(56.6mg, 0.543mrno1) in 2OmL of Et3N was added Pd(PPh3)2C12 (9.53mg, 0.Oi4mmol) and Cul (5.17mg, C.O27mmol). The mixture was protected with N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-1-IPLC to give the target product Compound 134(3mg, yield: 24.59%).LCMS: m/z 345 (M+H?H M?IR (400 MHz cDCI.) oe 8 78 (s 1H), 8 58 (s 1H) 8 O (s IH) 7 53 (d, 1= 8 8 Hz, 2H),7.35 (d, J:= 8.0 Hz, 2K), 6.51 (s, 1K), 2.38 (s, 3H).

The synthetic route of 153800-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 153800-11-4, name is 2-Ethynylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Ethynylpyrazine

To a solution of 223(100mg, 0347mmo1), 10(361mg, 0.347mmo1) in 20 mL of Et3N was added Pd(PPh3)2C12 (244mg, 0.347mmo1) and CuT (66.1mg. 0347mmo1). The mixture was protected under N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by PrepHPLC to give the target product Compound88(0mg, yield: 2180%),LCMS: m/z 265 (M+HY;1H NMR (400 MHz, CDCI3): oe 8.74 (d, J= 1.2 Hz, 1H), 8.588.57 (m, IH), 8.49 (d, J= 2.4Hz, 11:1), 813 (s, 1H), 793 (s, 1H), 768.-764 (in, 2H), 7.18 (t,J: 8.6Hz, 2H).

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 153800-11-4.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 153800-11-4, A common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, molecular formula is C6H4N2, 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 197(100mg, 0.3 i9mmol)) and 10(36.6mg, 0.35 Immol) in 2OmL of Et3N was added Pd(PPh3)2C12 (11.21mg, 0.Ol6mmoi)and Cul (608mg, 0.O32mmol)). The mixture was protected under N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep4IPLC to give the target productCompound 80(25mg, yield: 27.1 %).LCMS: m/z 290 (,ff:[)-F;?H NMR (400 MTIz, CDCl) 8 78 (hi 111), 8 62.-8 55 (mn 21fl 8 21 (S 11-fl 7 9? s il-fl 7.83 (s. 1H), 7.76-7.73 (m, 1H), 7.357.32 (m, 1H).

The synthetic route of 153800-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 153800-11-4,Some common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, molecular formula is C6H4N2, 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 227(100mg, 0.3O6mrnoI) and 10(63.7mg, 0.61 immol) in 2OmL of Et3N was added Pd(PPh3)2C12 (10.73mg, 0.OiSmrnoi) and CuT (5.82mg, 0.03 immol). The mixture was protected with N2 atmosphere, then was heated at 70C for 24 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-IPLC to give the target productCompound 103(18mg, yield: 1941 %).LCMS: m/z 304 (M+H)NMR (400 MHz, CDCI3): 5 8.668.65 (m, 3H), 7.67 (s, 1H), 7.60-7.57 (m, IH), 7.43.-7.40 (m, 1H), 6.55 (s, 11:1), 2.47 (s, 31:1).

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

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 153800-11-4, 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. 153800-11-4 name is 2-Ethynylpyrazine, 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 solution of 18i(i00m, 03i9mmol) and 10(66.5mg, 0.639mmo1) in 2OmL of Et3N wasadded Pd(PPh3)2C12 (11.21mg, 0Oi6mmoi) and CuT (608mg, 0O32mmoi). The mixture wasprotected with N: atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-i-IPLC to give the target product Compound 111(18mg, yield: 1948%).LCMS: rn/z 290 (M¡ÀH) +?H NMR (400 MHz, CDCI3): 5 8.84 (d, J 1.6 Hz, 1H), 8.63-8.62 (rn, IH), 8.55 (d, J= 2.4 Hi, 111) 97 (d 1 2 S Hi III) 7 8 (t, 1H? 7 79 (d 1 9 2 hi ill) 4- 2 (in, 111), 6.83 (d, J:::: 2.4 Hz, IH),

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

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem