Category: 20260-53-1

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. 20260-53-1, name is Nicotinoyl chloride hydrochloride, molecular formula is C6H5Cl2NO, 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. Formula: C6H5Cl2NO

To a mixture of N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (94.8 mg, 0.30 mmol) and isonicotinoyl chloride hydrochloride (56.1 mg, 0.32 mmol) in THF (2.0 mL) at room temperature was added N,N-diisopropylethylamine (0.157 mL, 0.90 mmol). After stirring for 3 hours at room temperature, an additional 21 mg of isonicotinoyl chloride hydrochloride was added and the reaction continued for 17 hours. The reaction was quenched with H2O, then treated with an EtOAc/saturated NaHCO3(aq) solution work-up to give an off-white solid. The solid was recrystallized from EtOAc/hexane to afford a white solid (115 mg, 91%). (0276) 1H NMR (300 MHz, DMSO-d6) delta ppm 2.76-2.95 (m, 2H) 3.52-3.59 (m, 1H) 3.61 (s, 3H) 3.74 (s, 6H) 3.95 (t, J=6.74 Hz, 1H) 4.43 (br. s., 1H) 4.71 (s, 1H) 7.17-7.27 (m, 2H) 7.39-7.56 (m, 2H) 8.19 (s, 0.37H, minor rotamer) 8.42 (s, 0.63H, major rotamer) 8.67-8.74 (m, 2H) 9.44 (br. s., 1H).

With the rapid development of chemical substances, we look forward to future research findings about 20260-53-1.

Reference:
Patent; Allergan, Inc.; Wurster, Julie A.; Malone, Thomas C.; Hull, III, Clarence Eugene; Rao, Sandhya; Yang, Rong; Yee, Richard; (24 pag.)US9296747; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20260-53-1, 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. 20260-53-1, name is Nicotinoyl chloride hydrochloride. A new synthetic method of this compound is introduced below.

To a solution of 1 (50 mg, 0.071 mmol) in 354 ml of pyridine at room temperature was added nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) followed by triethylamine (23 ml, 0.170 mmol). After stirring for 1.5 h, 4-dimethylamino pyridine (8.6 mg, 0.071 mmol) was added. After stirring 5 h, additional triethylamine (23 ml, 0.170 mmol), 4-dimethylamino pyridine (8.6 mg, 0.071 mmol), and nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) was added along with a 50 ml pyridine rinse. After stirring 18 h the reaction was treated with 0.5 ml of saturated aqueous sodium bicarbonate and washed with methylene chloride (4×1 ml). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to a light brown oil. Chromatography (14 g of flash silica gel), eluting with ethyl acetate-hexanes (10:1) provided 49 mg (85%) of the free base as a white foam. The nicotinoate was dissolved in 1 ml of methylene chloride and treated with a 1.0 M solution of hydrogen chloride in diethyl ether (90 ml, 0.090 mmol). The clear, colorless solution was allowed to stand at room temperature for 5 min. Removal of the solvent in vacuo produced 51 mg of the title compound as a white foam: 500 MHz 1H NMR (CDCl3) d 8.94 (s, 1H), 8.78 (br s, 1H), 8.29 (d, 1H, J=7.0 Hz), 7.57 (br s, 1H), 7.38 (d, 2H, J=7.1 Hz), 7.30-7.16 (m, 5H), 7.10 (dd, 1H, J=8.4, 1.7 Hz), 6.88 (d, 1H, J=8.4 Hz), 6.71 (m, 1H), 5.80 (d, 1H, J=15 Hz), 5.74 (d, 1H, J=9.6 Hz), 5.56 (br s, 1H), 5.00 (d, 1H, J=9.6 Hz), 4.95 (t, 1H, J=8.9 Hz), 4.84 (d, 1H, J=9.8 Hz), 4.77-4.72 (m, 1H), 3.91 (s, 3H), 3.39 (dd, 1H, J=13, 8.2 Hz), 3.23-3.14 (m, 2H), 3.06 (dd, 1H, J=14, 7.6 Hz), 2.81-2.74 (m, 1H), 2.62-2.45 (m, 2H), 1.93 (ddd, 1H, J=14, 12, 4.8 Hz), 1.78-1.70 (m, 1H), 1.66-1.59 (m, 1H), 1.25 (s, 3H), 1.20 (d, 3H, J=7.0 Hz), 1.19 (s, 3H), 0.98 (d, 3H, J=6.7 Hz), 0.84 (d, 3H, J=6.5 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20260-53-1, Nicotinoyl chloride hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; Wayne State University; University of Hawaii; US6680311; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20260-53-1, 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 20260-53-1 as follows.

A suspension of /e/7-butyl 5-(6-acetoxy-2-(3-aminophenyl)quinazolin-4- y.amino)- l H-indazole-1-carboxylate (0 5Og, 0 98 mmol), nicotinoyl chloride hydrochloride (0 224g, 1 26 mmol) and DIEA (0 45g, 3 48 mmol) in CH2Cl2 (15 niL) was stirred at RT for 7 h The volatiles were removed in vacuo and the residue was purified by preparative TLC (SiO2, CH2Cl2-MeOH 9.1 ) to give the product te/7-butyl 5-(6-acetoxy-2- (3-(nicotinamido)phenyl)quinazolin-4-ylamino)-1H-indazole-l -carboxylate (0.374g, 0 608mmol, 62%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20260-53-1, its application will become more common.

Reference:
Patent; SURFACE LOGIX, INC.; SWEETNAM, Paul; BARTOLOZZI, Alessandra; CAMPBELL, Anthony; COLE, Bridget; FOUDOULAKIS, Hope; KIRK, Brian; SESHADRI, Hemalatha; RAM, Siya; WO2010/104851; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20260-53-1, 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. 20260-53-1, name is Nicotinoyl chloride hydrochloride. A new synthetic method of this compound is introduced below.

jOZllj To a stirred solution of 4-aminobeuzene-1,3-diol hydrochloride (0.50 g, 3.09 mmol) in pyridine (6 mL) with ice cooling, was added ilicotinoyl chloride hydrochloride (0.55 g, 3.09 mmol) portion-wise. The mixture was stirred at room temperature for 16 hours. The mixiure was concentratci1 in vucuo and the residue was diluted with water (50 mL) and extracted with ethyl aceffite (2 x 60 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by FCC (silica, 30-100% ethyl acetate in heptane) gave the title compound 148 mg (21% yield) as a light brown solid. 6H NMR (250 MHz, DMSO) 9.47 (d, J= 88.0 Hz, 3H), 9.10 (d, J = 1.7 Hz, 1R), 8.73 (dd, J = 4.8, 1.5 Hz, 1H), 8.28 (dt, J = 7.9, 1.9 Hz, 1H), 7.53 (dd, J = 7.7, 5.1 Hz, 1H), 7.20 (d, J = 8.6 Hz, 1H),6.36 (d, I = 2.6 Hz, 1H), 6.24 (dd, J = 8.6, 2.6 Hz, 1H). Tr(METCRI27S) = 0.79 mm, (ESt) (MtH)t 23 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20260-53-1, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 20260-53-1 , The common heterocyclic compound, 20260-53-1, name is Nicotinoyl chloride hydrochloride, molecular formula is C6H5Cl2NO, 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 nicotinyl chloride hydrochloride (3.16 g, 17.76 mmol) and LI-2c (3 g, 11.84 mmol) in THF (50 mL) was added TEA (8.3 mL, 59.2 mmol) and stirred overnight at RT. After usual aqueous work-up and chromatographic purification, 4.14 g (97%) of LI-2c-nicotinate ester was obtained as a colorless oil. 1H NMR (CDCl3, 300 MHz): delta 1.43 (s, 9H), 2.82 (t, 2H, J=6.31 Hz), 3.42-3.48 (q, 2H), 4.62 (t, 2H, J=6.59 Hz), 7.29-7.33 (m, 1H), 8.30 (d, 1H, J=7.95 Hz), 8.78 (dd, 1H, J=4.86, 1.72 Hz), 9.23 (d, 1H, J=2.13 Hz). MS: m/z 358 [M+H]+, 381 [M+Na]+, 739 [2M+Na]+.

The synthetic route of 20260-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Satyam, Apparao; US2006/46967; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 20260-53-1, 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. 20260-53-1, name is Nicotinoyl chloride hydrochloride. A new synthetic method of this compound is introduced below.

a. Preparation of 4-chloro-2-(pyridin-3-yl)quinazoline. To a solution of 2-aminobenzonitrile (5.90 g, 50 mmol) in sulfolane (20 mL) was added nicotinoyl chloride hydrochloride (12.0 g, 67.4 mmol), and the mixture was stirred at 100 C. for 16 hr. PCl5 (18.2 g, 87.5 mmol) was added in one portion, and stirred at 100 C. for 10 hr. The mixture was cooled to room temperature, and carefully poured into 400 mL saturated sodium bicarbonate solution cooling with ice bath. The solid was filtered, washed with water, dried, and purified by flash chromatography to give 5.50 g (46%) light-yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.76 (d, J=1.3 Hz, 1H), 8.82 (dt, J=8.0, 1.9 Hz, 1H), 8.73 (dd, J=4.7, 1.4 Hz, 1H), 8.26 (dd, J=8.4, 0.8 Hz, 1H), 8.10 (d, J=8.4 Hz, 1H), 7.95 (ddd, J=8.4, 7.0, 1.4 Hz, 1H), 7.69 (ddd, J=8.2, 7.0, 1.1 Hz, 1H), 7.44 (dd, J=7.5, 4.8 Hz, 1H). 13C NMR: (100 MHz, CDCl3) delta(ppm): 162.9, 158.3, 151.8, 151.7, 150.3, 136.1, 135.2, 132.4, 129.1, 128.9, 126.0, 123.5, 122.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20260-53-1, Nicotinoyl chloride hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Northwestern University; Krainc, Dimitri; Silverman, Richard B.; Zheng, Jianbin; (76 pag.)US2017/1976; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem