Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 1374639-78-7, tert-Butyl 4-(6-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate, 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, Application In Synthesis of tert-Butyl 4-(6-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl 4-(6-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate

To the solution of tert-butyl 4-(6- { [7-cyclopentyl-6-(dimethylcarbamoyl)-7H- pyrrolo[2, 3 -d]pyrimidin-2-yl] amino } pyridin-3 -yl)piperazine- 1 -carboxylate (6.0 g)in 15 ml of DCM was added TFA (15 ml) at 5-10C. The solution was stirred over3-4 hrs at 20-30C. To this was added methyl tertiary butyl ether (60 ml) and stirred for 2-3 hrs at 15-25C. The solid was collected by filtration followed by drying at 40-50C to give crystalline form I of 4-(6-{[7-cyclopentyl-6- (dimethylcarbamoyl)-7H-pyrrolo[2,3 -d]pyrimidin-2-yl] amino } pyridin-3 -yl)piperazin- 1 -ium-trifluoro acetate (100 g).Yield: 99.0 %; HPLC Purity: 99.8%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1374639-78-7, tert-Butyl 4-(6-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LTD.; SOKHI, Sarbjot Singh; SINGH, Govind; LAHIRI, Saswata; PANDEY, Maneesh Kumar; TIWARI, Raj Narayan; SHUKLA, Sonu; MUSMADE, Sachin; DUA, Heena; CABRI, Walter; (70 pag.)WO2019/82143; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14667-47-1, Methyl 2-aminonicotinate, 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, COA of Formula: C7H8N2O2, blongs to pyridine-derivatives compound. COA of Formula: C7H8N2O2

Preparation 76: 2-Amino-5-(4-fluorophenoxy)nicotinic add methyl ester To 2-aminonicotimc acid methyl eater (5.5g, 36.2mmol) in DMF (70mL) was added N-iodosuccinimide (9.8g, 43.7rmnol). After 16h the mixture was poured into sat. sodium thiosulfite solution and then extracted with Et20. The organic phase was washed with water, brine, dried (MgS04) and the solvent was removed in vacuo to give 2-amino-5-iodonicotinic acid methyl ester. To 4-fluorophenol (2.4g, 21.6mmol) in dioxane (50mL) was addedCS2CO3 (6g, 25.2mmol) and the mixture was heated to 50C. After 20min Cul (0.56g, 3.0mmol) and 2-ammo-5-iodonicotrriic acid methyl ester (2g, 7.2mmol) were added and the mixture heated under reflux for 16h. After cooling the solvent removed in vacuo, the residue was partitioned between EtOAc and 4N HQ, the organic phase was extracted with 6N HC1 and the organic phase discarded. The combined aqueous phase was basified with NH4OH and re-extracted with EtOAc. The organic phase was dried (MgS04) and the solvent was removed in vacuo. The residue was purified by column chromatography (1 :3EtOAcrHexane) to give, after removal of the solvent in vacuo, the title compound: RT= 3.30min; m/z (ES+) = 263.2 [M+ Iff”.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14667-47-1, Methyl 2-aminonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; PROSIDION LIMITED; BLOXHAM, Jason; BRADLEY, Stuart Edward; SAMBROOK-SMITH, Colin Peter; SMYTH, Donald; KEILY, John; DAWSON, Graham John; RASAMISON, Chrystelle Marie; BELL, James Charles; WO2011/117254; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 614750-81-1, 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. 614750-81-1, name is [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde, molecular formula is C7H5N3O, 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.

To a solution of [l,2,4]triazolo[l,5-a]pyridine-6-carbaldehyde (2.5 g, 0.0169 mol) in a mixed solvent of THF (40 mL) and iPrOH (10 mL), was added (phenylamino-(2-methyl- pyrimidin-4-yl)-methyl)-phosphonic acid diphenyl ester (7.33 g, 0.0169 mol; see Example l(b) above) and Cs2CO3 (7.26 g, 0.022 mol). It was stirred at room temperature for 48 hours and then treated with 3N HCl (10 mL) for 1 hour. The reaction mixture was then diluted with methyl t-butyl ether and extracted with IN HCl twice. The combined aqueous layers were neutralized with 30percent aqueous KOH to pH of ca. 8, then extracted with ethyl acetate (3x). Organic layers were dried over MgSO4 and concentrated to yield a dark orange oil, which was purified on silica gel column with EtOAc/hexane (4:1) to give l-(2-methyl-pyrimidin-4-yl)-2- [l,2,4]triazolo[l,5-a]pyridin-6-yl-ethanone (4.15 g, 97percent) as a yellow solid. 1H NMR (300 MHz, CDCl3), delta 8.94 (d, IH), 8.62 (s, IH), 8.34 (s, IH), 7.76 (d, IH), 7.75 (s, IH), 7.51 (d, IH), 4.61 (s, 2H), 2.90 (s, 3H).

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 614750-81-1, [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde.

Reference:
Patent; BIOGEN IDEC MA INC; WO2006/26305; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16179-97-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, molecular weight is 173.6, as common compound, the synthetic route is as follows.

A flask was charged with 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide TFA salt (25 mg, 0.05 mmol) (as prepared in Example 14, step (b)), pyridin-2-yl-acetic acid hydrochloride (10 mg, 0.06 mmol), EDCI (12 mg, 0.06 mmol), HOBt (8.0 mg, 0.06 mmol), DIEA (36 muL, 0.20 mmol) and 0.2 mL DMF and stirred at 25 C. for 10 h. The reaction was diluted with 2 mL of H2O and the title compound was purified by RP-HPLC (C18), eluting with 30-50% CH3CN in 0.1% TFA/H2O over 9 min to give 22 mg (70%) of a white solid. 1H-NMR (400 MHz, CD3OD): delta 8.82 (d, 1H), 8.52 (t, 1H), 8.14 (d, 1H), 8.04 (s, 1H), 7.96 (m, 3H), 7.20 (dd, 1H), 7.10 (d, 1H), 5.82 (m, 1H), 4.68 (m, 1H), 4.32 (m, 2H), 4.18 (m, 1H), 3.40 (m, 1H), 2.88 (m, 2H), 2.30 (m, 4H), 2.06-1.60 (m, 8H). Mass spectrum (ESI, m/z): Calcd. for C29H30N6O2, 495.2.2 (M+H), found 495.2.

The chemical industry reduces the impact on the environment during synthesis 16179-97-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; Johnson, Dana L.; Tuman, Robert W.; US2006/281788; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 141-86-6, 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 141-86-6 as follows.

8.9 2-Amino-7-hydroxy-1,8-naphthyridine 2,6-Diaminopyridine (20?g, 0.18?mol) and (dl)-malic acid (27?g, 0.2?mol) were placed into a 500?mL three-neck round bottomed flask fitted with an addition funnel, thermometer, and mechanical stirrer. The stirred mixture was cooled in an ice-water bath and concentrated sulfuric acid (100?mL) was added drop-wise. The rate of addition was controlled to maintain an internal temperature ?45?C during the addition. Next, the addition funnel was replaced by a reflux condenser and the slurry was heated to an internal temperature of 110?C for 3?h. The solution was transferred to a 1L beaker, cooled to 0?C by an ice-water bath and was made basic (pH?=?8) by careful addition of NH4OHaq (300?mL). The crude brown solid was collected by vacuum filtration and was washed on the filter-paper with water (2?L). The solid was triturated with 1:9 (v:v) water: methanol and again collected by vacuum filtration, affording 7-amino-2-hydroxy-1,8-naphthyridine as a tan powder. Yield: 25?g (86%). 1H NMR (500?MHz, DMSO-d6): delta?=?11.91 (br s, 1H), 7.65 (d, J?=?9.5, 1H), 7.65 (d, J?=?8, 1H), 7.03 (br s, 2H), 6.34 (d, J?=?8.5, 1H), 6.12?ppm (d, J?=?9.2, 1H); 13C NMR (126?MHz; DMSO-d6): delta?=?163.8, 160.6, 150.4, 139.8, 137.4, 114.8, 105.3, 105.0?ppm; MS (ESI; CH3OH): m/z 162.0664 ([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,141-86-6, its application will become more common.

Reference:
Article; Sarkar, Mithun; Pandey, Pragati; Bera, Jitendra K.; Inorganica Chimica Acta; vol. 486; (2019); p. 518 – 528;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19337-97-4, 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. 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid, molecular formula is C8H7NO2, 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.

To a solution of (E)-3-(pyridin-3-yl)acrylic acid (0.40 g, 2.68 mmol, 1 eq) in DMF dry (4.0 mL), ammonium chloride (0.85 g, 16.10 mmol, 6 eq), HOBt (0.52 g, 3.86 mmol, 1.44 eq), EDCI (0.74 g, 4.20 mmol, 1.44 eq) and N-methylmorpholine (0.43 mL, 3.90 mmol, 1.44 eq) were subsequently added. The reaction was stirred at room temperature, under nitrogen for 3 h. After adding water, the reaction was filtered off through a neutral alumine oxide pad, washing with EtOAc/MeOH 9:1 (3 * 10 mL). The filtrate was evaporated and the residue was purified by column chromatography, using EtOAc/MeOH 9:1 as eluant to give 5 as white solid after crystallization with EtOAc (0.34 g, 85%). Mp 154-156 C. 1H NMR (300 MHz, CD3OD) delta 8.71 (d, J = 2.1 Hz, 1-H), 8.51 (dd, J = 4.9/1.5 Hz, 1-H), 8.05 (dt, J = 7.9/1.8 Hz, 1-H), 7.57 (d, J = 15.9 Hz, 1-H), 7.47 (dd, J = 7.9/4.9 Hz, 1-H), 6.77 (d, J = 15.9 Hz, 1-H); 13C NMR (75 MHz, CD3OD) delta 168.6, 149.5, 148.2, 137.1, 135.0, 131.5, 124.3, 123.1; MS (ESI) m/z 149 (M + H)+; IR (KBr) 3151, 3036, 2370, 1683, 1604, 1400, 980 cm-1. Anal. Calcd for C8H8N2O: C, 64.85; H, 5.44; N, 18.91. Found: C, 64.54; H, 5.12; N, 19.20.

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 19337-97-4, trans-3-(3-Pyridyl)acrylic acid.

Reference:
Article; Galli, Ubaldina; Mesenzani, Ornella; Coppo, Camilla; Sorba, Giovanni; Canonico, Pier Luigi; Tron, Gian Cesare; Genazzani, Armando A.; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 58 – 66,9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 573762-62-6 ,Some common heterocyclic compound, 573762-62-6, molecular formula is C7H4F3N3, 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.

General procedure: To a solution of compound 5 (50mg, 0.26mmol) and compound 11 (66mg, 0.26mmol) in DMA (0.5ml) was added thiophosgene (32mg, 0.26mmol) under N2. The reaction mixture was stirred for 16h at 60C. To this mixture were added MeOH (2ml) and 2M HCl (2ml), then the reaction mixture was reflux for 2h. After cooling to room temperature, the reaction mixture was poured into ice water (10ml) and extracted with EtOAc (10ml). The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silics gel (EA/PE=1/1) to afford 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluoro-N-methylbenzamide (18) (51.3mg, 41%).

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. 573762-62-6, 5-Amino-3-(trifluoromethyl)picolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pang, Xuehai; Wang, Yingwei; Chen, Yuanwei; Bioorganic and Medicinal Chemistry Letters; vol. 27; 12; (2017); p. 2803 – 2806;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 754230-78-9, name is 3-(Benzyloxy)-5-bromopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-(Benzyloxy)-5-bromopyridin-2-amine

Under argon, 200 g (0.72 mol) of 3-(benzyloxy)-5-bromopyridine-2-amine from Example 1 6A, 590 g (3.58 mol) of ethyl 2-chloroacetoacetate and 436 g of 3 Amolecular sieve were suspended in 6 1 of ethanol, and the suspension was stirred at reflux for 72 h. The reaction mixture was filtered oil through silica gel and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=9: 1, then 6:4) and the product fractions were concentrated. This gave 221 g (79% of theory) of the target compound.10595] LC-MS (Method 16): R=1.31 mm10596] MS (ESpos): mlz=389 (M+H)j0597] ?H-NMR (400 MHz, DMSO-d5): oe=1.36 (t, 3H), 2.58 (s, 3H), 4.32-4.41 (m, 2H), 5.33 (s, 2H), 7.28-7.32 (m, 1H), 7.36-7.47 (m, 3H), 7.49-7.54 (m, 2H), 8.98 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 754230-78-9.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (95 pag.)US2016/347770; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1824-81-3, 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 1824-81-3 as follows.

An alkali trap, an equal pressure dropping funnel, a thermometer, and a mechanical stirrer were attached to a 1000 mL four-necked round bottom flask. (A) 2-amino-6-picoline (27.0 g 0.25 mol) and 48% HBr (125 mL 2.31 mol) were placed in this reaction vessel. The reaction vessel was immersed in an ice bath and cooled to 0 C. Br2 (37.5 mL 0.72 mol) was transferred to an equal pressure dropping funnel, The temperature of the reaction solution was kept at 0 C. and slowly dropped into the reaction vessel over 90 minutes while vigorously stirring with a mechanical stirrer. NaNO 2 (42.5 g 0.62 mol) was weighed and dissolved in about 100 mL of distilled water. This was transferred to an equal pressure dropping funnel,While stirring vigorously with a stirrer, it dripped over about 2 hours. At this time, care was taken that the temperature of the reaction solution did not exceed 10 C. In order to complete the reaction, NaNO 2 (2.50 g 0.036 mol) was dissolved in about 10 mL of distilled water and added, It was confirmed that nitrogen gas was not generated from the reaction vessel. While cooling in an ice bath, NaOH (95.0 g, 2.4 mol) was dissolved in about 300 mL of distilled water, after cooling sufficiently, it was gradually added to the solution for neutralization. At this time, care was taken that the temperature of the reaction solution did not exceed 20 C. The reaction mixture was extracted with Et 2 O (200 mL × 4) and the organic layer was collected. Anhydrous Na 2 SO 4 was added and dried, Upon concentration, a brown oily substance was obtained. This oily substance was distilled under reduced pressure in a rectifying tube, fractionated at 55 C. to 60 C. at a reduced pressure degree of 7.00 mmHg, A yellow oily substance was obtained. This material was stored at -40 C. Yield: 72% (32.0 g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1824-81-3, its application will become more common.

Reference:
Patent; THE DOSHISHA; KODERA, MASAHITO; TSUJI, TOMOKAZU; (18 pag.)JP2017/197451; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41404-58-4, 2-Bromo-5-fluoropyridine, 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, 41404-58-4, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(Related precendent, see Reider et al., Tett. Lett., 41, 2000, 4335-4338). Into a flask containing 2-Bromo-5-fluoro-pyridine (purchased from Aldrich, 2.5 g, 14.30 mmol, 1 eq) was dissolved toluene (143 mL, 0.1 M) and DMF (1.44 mL, 18.58 mmol, 1.3 eq, anhydrous) before being cooled to 78 C. under an inert atmosphere. nBuLi (17.1 mL, 17.14 mmol, 1 M hexanes) was added dropwise via an addition funnel over 15 min and allowed to stir for 90 min. To the mixture was added NaBH4 (1.08 g, 28.60 mmol, 2 eq) and the reaction allowed to warm up to room temp. The reaction was quenched with saturated NH4Cl and dissolved in EtOAc (300 mL). It was washed with water (2×100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Flash column chromatography was used to purify the product using hexanes/Ethyl acetate (3/7) as eluent to furnish desired alcohol 148. 1H NMR (300 MHz) CDCl3 delta: partial 4.75 (s, 2H), 3.67 (bs, 1H). 19F NMR (300 MHz) CDCl3 delta: -129.80. MS: 127.96 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,41404-58-4, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; US2007/72831; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem