53554-20-4 | Pyridine-derivatives

Analyzing the synthesis route of 53554-20-4

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. 53554-20-4, 6-Amino-2-chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Related Products of 53554-20-4 ,Some common heterocyclic compound, 53554-20-4, molecular formula is C6H4ClN3, 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.

38 (1.00g crude, max 4.30mmol), diethylzinc (1.0M in hexane, 7.81mmol, 7.8mL), and Pd2(PPh3)4 (150mg, 0.13mmol) were added to a microwave vial along with NMP (8mL). The vial was flushed with N2, sealed and heated using microwave irradiation at 100C for 30min. The contents of the vial were cooled to rt and washed with sat. aq. NaHCO3 (120mL), and H2O (120mL), dried over Na2SO4, and evaporated under vacuum. Purification by FC (heptane/EtOAc 80:20 to 50:50) afforded the product as brown solid (333mg, 53% over 2 steps). 1H NMR (CDCl3) delta 7.56 (d, J=8.5Hz, 1H), 6.34 (d, J=8.5Hz, 1H), 4.99 (b s, 2H), 2.86 (q, J=7.6Hz, 2H), 1.31 (t, J=7.6Hz, 3H). 13C NMR (CDCl3) delta 167.4, 159.8, 141.4, 118.5, 105.7, 96.6, 30.4, 13.5.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some tips on 53554-20-4

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, 53554-20-4, 6-Amino-2-chloronicotinonitrile.

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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Amino-2-chloronicotinonitrile

6-Amino-2-chloronicotinonitrile (250 mg, 1.628 mmol), 1- (methylsulfonyl)piperazine, HC1 (1307 mg, 6.51 rnmo]) and potassium carbonate (675 mg, 4.88 mmol) were suspended in DMA (5426 m). The reaction mixture was heated to 105 C overnight, cooled to rt and stirred for 72 h. The reaction ws decanted into a separatory funnel containing EtOAc and H20, rinsing the residual K2CO3 with EtOAc. The aqueous layer was extracted with EtOAc (2X) and the combined organics were washed with 10% LiCl solution before drying (MgS04) and concentrating to a cream solid to afford the titled product (461 mg, 85% purity, 86% yield). This material was used as is in the subsequent reactions. 1H NMR (4QQMHz, DMSO-d6) d 7.52 (d,.1 8.4 Hz, 1 1 1). 6 83 (br s, 2H), 6.46 (d, 1=8.7 Hz, 1H), 5.99 (d, J=8.4 Hz, 1H), 3.68 – 3.54 (m, 4H), 3.27 – 3.12 (m, 4H), 2.92 (s, 3H); LC/MS [M+H] = 282.2; LC RT 0.63 min; (Column: BEH 08 2.1 x 50mm; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: acetonitrile with 0.05% TFA; Temperature: 50 C; Gradient: 2-98% B over 1.7 min; Flow: 0.8 mL/min).

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, 53554-20-4, 6-Amino-2-chloronicotinonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TARBY, Christine M.; NORRIS, Derek J.; LO, Julian C.; AHUJA, Vijay T.; SEITZ, Steven P.; GAVAI, Ashvinikumar V.; TOKARSKI, John S.; RAJASAGI, Mohini; WICHROSKI, Michael; BROEKEMA, Matthias; (155 pag.)WO2019/213340; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new synthetic route of 6-Amino-2-chloronicotinonitrile

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53554-20-4, 6-Amino-2-chloronicotinonitrile, and friends who are interested can also refer to it.

Reference of 53554-20-4, 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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile. A new synthetic method of this compound is introduced below.

38 (500mg, 3.25mmol), phenylboronic acid (595mg, 4.88mmol), K3PO4 (1.73g, 8.14mmol) and Pd(PPh3)4 (0.16mmol) were added to a microwave vial together with toluene/ EtOH (10:1, 11mL). The vial was flushed with N2, sealed and heated under microwave irradiation for 1h at 100C. The reaction mixture was cooled to rt, 1M NaOH (30mL) was added, and the mixture was extracted with EtOAc (2×30mL). The combined organic phase was dried over Mg2SO4 and evaporated under vacuum. Purification by DCVC (heptane/EtOAc 100:0 to 60:40) afforded the product as yellow solid (416mg, 65%). mp 204.1-204.9C. 1H NMR (CDCl3) delta 7.89-7.83 (m, 2H), 7.75 (d, J=8.8Hz, 1H), 7.54-7.47 (m, 3H), 6.50 (d, J=8.8Hz, 1H). 13C NMR (DMSO-d6) delta 161.0, 141.6, 138.0, 129.5, 128.4, 128.2, 119.7, 106.6, 92.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53554-20-4, 6-Amino-2-chloronicotinonitrile, and friends who are interested can also refer to it.

Some scientific research about 53554-20-4

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 53554-20-4, 6-Amino-2-chloronicotinonitrile.

Reference of 53554-20-4, 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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile, molecular formula is C6H4ClN3, The 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.

A mixture of NMP (8mL), I2 (82.6mg, 0.33mmol), and Zn (809mg, 12.4mmol) was stirred at rt until the red colour of I2 disappeared (ca. 4min). Butyl-1-bromide (0.88mL, 8.14mmol) was added and the mixture was stirred at 80C for 3h. The mixture was cooled to rt and 38 (1.00g crude, max. 4.30mmol) and Pd2(PPh3)4 (150mg, 0.13mmol) were added, and the reaction mixture was stirred at rt for 1h. Sat. aq. NH4Cl (120mL) was added, and the mixture was extracted with EtOAc (2×120mL). The combined organic phase was washed with brine (120mL), dried over Mg2SO4, and evaporated under vacuum. Purification by FC (heptane/EtOAc 100:0 to 0:100) afforded the product with small impurities as light yellow solid (225mg, 29% over 2 steps). 1H NMR (CDCl3) delta 7.56 (d, J=8.5Hz, 1H), 6.35 (d, J=8.5Hz, 1H), 5.00 (b s, 2H), 2.83 (t, J=8.8Hz, 2H), 1.66-1.79 (m, 2H), 1.43 (sxt, J=7.3Hz, 2H), 1.20-1.35 (m, 3H, impurity), 0.97 (t, J=7.3Hz, 3H), 0.90 (t, J=6.7Hz, 2H, impurity). 13C NMR (CDCl3) delta 166.3, 159.7, 141.1, 135.1 (impurity), 127.6 (impurity), 118.5, 105.5, 96.6, 36.7, 31.8 (impurity), 31.4, 29.0 (impurity), 22.6 (impurity), 22.4, 14.1 (impurity), 13.8.

Some scientific research about 6-Amino-2-chloronicotinonitrile

Reference of 53554-20-4, Adding some certain compound to certain chemical reactions, such as: 53554-20-4, name is 6-Amino-2-chloronicotinonitrile,molecular formula is C6H4ClN3, 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 53554-20-4.

To a 40 mL pressure vial were added 6-amino-2-chloronicotinonitrile (1.000 g, (0806) 6.51 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (1.423 g, 8.47 mmol), K2CO3 (1.350 g, 9.77 mmol), followed by 1,2-dimethoxy ethane (16 mL), water (8 mL) and then Pd(PPh3)4 (0.226 g, 0.195 mmol). Argon was bubbled through the mixture. The reaction mixture was heated at 80 C overnight in a heating block. The reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with brine. (0807) The organic layer was separated and concentrated. The material was purified using silica gel chromatography eluting with 0-80% B/DCM over 13 minutes. [B= 10% 2 N NH3 in MeOH/EtOAc]. The appropriate fractions were concentrated to afford 6-amino-2-(prop- l-en-2-yl)nicotinonitrile (0.878 g, 5.52 mmol, 85% yield), as an off-white solid. NMR (400 MHz, DMSO-de) delta 7.70 (d, J=8.8 Hz, IH), 7.01 (br. s., 2H), 6.42 (d, J=8.8 Hz, IH), 5.49-5.43 (m, 2H), 2.07 (t, J=l. l Hz, 3H).

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ARAUJO, Erika M. V.; CHEN, Yan; DASGUPTA, Bireshwar; DEGNAN, Andrew P.; HILL, Matthew D.; KUMI, Godwin Kwame; MASTALERZ, Harold A.; WITTMAN, Mark D.; PEARCE, Bradley C.; ZHANG, Guifen; (172 pag.)WO2019/90198; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some scientific research about 53554-20-4

Some scientific research about 6-Amino-2-chloronicotinonitrile

Simple exploration of 6-Amino-2-chloronicotinonitrile

With the rapid development of chemical substances, we look forward to future research findings about 53554-20-4.

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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile, molecular formula is C6H4ClN3, The 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. name: 6-Amino-2-chloronicotinonitrile

[00227j Step 1: 6-Amino-2-chloronicotinonitrile (0.100 g, 0.65 1 mmol) was taken in a sealed tube and dissolved in dioxane (3 mL) and NMP (0.2 mL). To that was added (R)pyrrolidin-3-ol (0.05 7 g, 0.651 mmol) and NMP (0.2 mL) and the set up was heated at 150 C for 18 h. The solvents were evaporated from the reaction mixture and the crudewas dissolved in water and made basic by adding NaHCO3 and was extracted with DCM(3 x 15 mL). The combined organic layer were dried and evaporated to get the product(80 mg, 42% yield) which was directly in the next reaction. LCMS 205.2 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 53554-20-4.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; DUNCIA, John V.; HYNES, John; NAIR, Satheesh K.; PITTS, William J.; KUMAR, Sreekantha R.; GARDNER, Daniel S.; MURUGESAN, Natesan; PAIDI, Venkatram Reddy; SANTELLA, Joseph B.; SISTLA, Ramesh; WU, Hong; WO2014/74675; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem