98139-15-2 | Pyridine-derivatives

Extended knowledge of 98139-15-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 98139-15-2, 4-Aminopicolinonitrile, 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: C6H5N3, blongs to pyridine-derivatives compound. COA of Formula: C6H5N3

Ethyl 4-chlorosulfonyl-3-fluoro-l-methyl-pyrrole-2-carboxylate (1500 mg, 5.56 mmol) was dissolved in dry pyridine (26.25 mL, 325.2 mmol). l-(trifluoromethyl)cyclopropan-l -amine (1392 mg, 11.1 mmol) was added and the mixture was stirred at 70C for 6 hours. The mixture was concentrated in vacuo. The obtained residue was purified by silica gel column (0877) chromatography using gradient elution from heptane to EtOAc (100:0 to 0: 100) yielding ethyl 3-fluoro- 1 -methyl-4-[[ 1 -(trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (1.21 g) as a beige powder. Ethyl 3-fluoro-l-methyl-4-[[l- (0878) (trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (0.15 g, 0.31 mmol) and (0879) 4-aminopyridine-2-carbonitrile (40.05 mg, 0.34 mmol) were dissolved in THF (3 mL) in a tube. The tube was flushed with nitrogen, capped with a septum and stirred at room temperature. To this was added lithium bis(trimethylsilyl)amide (0.76 mL, 1 M, 0.76 mmol) at once using a syringe. The obtained solution was stirred for 3 hours. Then ammonium chloride (aq. / sat. / 10 mL) was added and the layers where separated. Then it was extracted once using ethyl acetate (10 mL). The combined extracts were concentrated in vacuo and purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The obtained fractions were concentrated in vacuo and repurified by Prep HPLC on (RP SunFire Prep CI 8 OmicronBeta-10muetaiota,30chi150etaiotaetaiota). Mobile phase (0.25% NH4HCO3 solution in water, MeOH). The desired fractions were concentrated under reduced pressure and co-evaporated twice with methanol (2 X 20 mL) and dried in a vacuum oven at 55C for 18 hours resulting in compound 192 (51 mg) as a white powder. Method B: Rt: 0.90 min. m/z: 430.1 (M-H)” Exact mass: 431.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.14 – 1.30 (m, 4 H), 3.75 – 3.89 (m, 3 H), 7.57 (d, J=4.6 Hz, 1 H), 7.90 (dd, J=5.6, 2.1 Hz, 1 H), 8.21 (d, J=2.0 Hz, 1 H), 8.63 (d, J=5.7 Hz, 1 H), 9.15 (br. s., 1 H), 10.67 (br. s., 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The important role of 98139-15-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

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.98139-15-2, name is 4-Aminopicolinonitrile, molecular formula is C6H5N3, molecular weight is 119.124, as common compound, the synthetic route is as follows.COA of Formula: C6H5N3

To ethyl 3-fluoro-l -methyl -4-[[(lR)-2,2,2-trifluoro-l-methyl-ethyl]sulfamoyl]pyrrole-2- carboxylate (128 mg, 0.37 mmol)and 4-aminopyridine-2-carbonitrile (57.2 mg, 0.48 mmol) dissolved in dry THF (20 mL) at 0C under nitrogen atmosphere, lithium (0240) bis(trimethylsilyl)amide in toluene (1.5 mL, 1 M, 1.478 mmol) was added. The mixture was stirred 1 hour at 0C and further overnight at room temperature. The reaction mixture was quenched with NH4C1 solution (30 mL) and extracted with EtOAc (50 mL), diluted with brine (50 mL) and extracted again with EtOAc (50 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated. The residue (dissolved in 1 mL DMF) was purified by column chromatography on silica gel using a 120g Reveleris cartridge with a gradient from 10 till 100% EtOAc in heptane. The product fractions were concentrated and the solid residue was crystallised from warm methanol (20 mL) upon addition of water. The light yellow crystals were filtered off and dried in vacuo at 50C overnight, resulting in compound 18 (47 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.18 (d, J=6.8 Hz, 3 H), 3.82 (s, 3 H), 3.93 – 4.04 (m, 1 H), 7.62 (d, J=4.4 Hz, 1 H), 7.91 (dd, J=5.7, 2.2 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H), 8.60 – 8.69 (m, 2 H), 10.72 (s, 1 H). Method D: Rt: 1.70 min. m/z: 418.0 (M-H)~ Exact mass: 419.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

The important role of 98139-15-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Some tips on 98139-15-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

P0C13 (0.3 mE) was added dropwise to a solution consisting of 1 -(naphthalen- 1 -yl)-5-(trifluoromethyl)-i Hpyrazole-4-carboxylic acid 2b (150 mg, 0.490 mmol), 4-aminopicolinonitrile (64.2 mg, 0.53 9 mmol) and pyridine (5 mE). The mixture was stirred at 0 C. for 1 h. The resulting mixture was concentrated under reduced pressure to give a crude product, which was purified by preparative HPEC (40% to 70% (v/v) ACN and H20 with 0.05% NH3) to afford compound 1. Compound 1 was concentrated to dryness under reduced pressure (101.30 mg, 5 1%). ECMS (ESI): RT=5.45 mm, mass calcd. for C2,H,2F3N50 407.348, mlz found 408.0 [M+H]. ?H NMR (400 MHz, DMSO-d5) oe ppm 11.31 (s, 1H), 8.71 (d, J=5.2 Hz, 1H), 8.56 (s, 1H), 8.30 (s, 1H), 8.26 (d, J=8.0 Hz, 1H), 8.15 (d, J=8.0 Hz, 1H),8.00 (d, J=4.0 Hz, 1H), 7.83-7.77 (m, 1H), 7.76-7.62 (m, 3H), 7.14 (d, J=8.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Extended knowledge of 98139-15-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Methyl 4-(tert-butylsulfamoyl)-3-chloro-l -methyl -pyrrole-2-carboxylate (50 mg, 0.16 mmol) and 4-aminopyridine-2-carbonitrile (0.021 g, 0.18 mmol) were dissolved in THF (5 mL) and cooled in an ice bath. To this was added dropwise lithium bis(trimethylsilyl)amide in toluene (0.32 mL, 1 M, 0.32 mmol) over a period of 5 minutes. The resulting mixture was allowed to reach room temperature and was stirred for 3 hours. The resulting mixture was quenched using ammonium chloride (10 mL / aq. sat.). This was extracted using ethylacetate (3 X 20 mL). The combined extracts were washed with brine (20 mL), dried on Na2S04, filtered and concentrated in vacuo. The obtained crude was purified by silica gel column chromatography using gradient elution from heptane to iPrOH. (100:0 to 70:30). The desired fractions were concentrated in vacuo and dried in a vacuum oven at 55 C for 24 hours yielding compound 6 (10 mg) as a bright white powder. Method B; Rt: 0.91 min. m/z : 394.0 (M-H)~ Exact mass: 395.1. 1H NMR (0198) (400 MHz, DMSO-d6) delta ppm 1.18 (s, 9 H), 3.79 (s, 3 H), 7.38 (s, 1 H), 7.65 (s, 1 H), 7.90 (dd, J=5.6, 2.1 Hz, 1 H), 8.20 (d, J=2.0 Hz, 1 H), 8.63 (d, J=5.5 Hz, 1 H), 10.97 (br. s., 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Analyzing the synthesis route of 98139-15-2

With the rapid development of chemical substances, we look forward to future research findings about 98139-15-2.

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. 98139-15-2, name is 4-Aminopicolinonitrile, molecular formula is C6H5N3, 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. COA of Formula: C6H5N3

l-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]-lH-pyrrole-2-carboxylic acid (200 mg, (0182) 0.729 mmol) was dissolved in DMF (1.7 mL) and triethylamine (0.41 mL, 2.9 mmol) and HATU (360 mg, 0.95 mmol) were added. After 10 minutes 4-aminopyridine-2-carbonitrile (174 mg, 1.46 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 42 hours. The mixture was poured into water (50 mL) and the organics were extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (Na2S04) and concentrated to dryness. The residue was purified using silica gel column chromatography (ethyl acetate in heptane from 0 to 100%) followed by prep. HPLC (Stationary phase: RP SunFire Prep C18 OBD-IotaOmicronmuiotaeta, 30 x 150mm), Mobile phase: 0.5% NH4OAc solution in water + 10% CH3CN, MeOH), resulting in compound 1 (4.6 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.54 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.4 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.43 (s, 1 H), 7.66 (d, J=1.3 Hz, 1 H), 7.86 – 8.12 (m, 2 H), 8.26 (d, J=2.0 Hz, 1 H), 8.60 (d, J=5.7 Hz, 1 H), 10.68 (br. s., 1 H). Method A; Rt: 1.22 min. m/z : 374.0 (M-H)~ Exact mass: 375.1.

With the rapid development of chemical substances, we look forward to future research findings about 98139-15-2.

Analyzing the synthesis route of 98139-15-2

With the rapid development of chemical substances, we look forward to future research findings about 98139-15-2.

Extended knowledge of 98139-15-2

According to the analysis of related databases, 98139-15-2, the application of this compound in the production field has become more and more popular.

Electric Literature of 98139-15-2, Adding some certain compound to certain chemical reactions, such as: 98139-15-2, name is 4-Aminopicolinonitrile,molecular formula is C6H5N3, 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 98139-15-2.

Into a 30-mL sealed tube, was placed 2-bromo-5-methoxy-4-[3-(pyrrolidin-l- yl)propoxy]pyridine (314 mg, 1.00 mmol, 1.00 equiv.), 4-aminopyridine-2-carbonitrile (240 mg, 2.01 mmol, 2.00 equiv.), Pd2(dba)3-chloroform (0.1 g, 0.10 equiv.), t-BuXPhos (0.085 g, 0.20 equiv.), Cs2C03 (970 mg, 2.97 mmol, 3.00 equiv.), dioxane (10 mL). The resulting solution was stirred for 16 h at 110 C in an oil bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The organic layer was washed with 1×50 mL of brine, dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (3 mL) was purified by Flash- Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN_Water=l :5 increasing to MeCN_Water=10: l within 120 min; Detector, UV 254 nm. 70 mg product was obtained. This resulted in 70 mg (20%) of 4-([5-methoxy-4-[3- (pyrrolidin-l-yl)propoxy]pyridin-2-yl]amino)pyridine-2-carbonitrile as an off-white solid.

According to the analysis of related databases, 98139-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new synthetic route of 4-Aminopicolinonitrile

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference of 98139-15-2, 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. 98139-15-2, name is 4-Aminopicolinonitrile. A new synthetic method of this compound is introduced below.

Ethyl 4-chlorosulfonyl-3-fluoro-l-methyl-pyrrole-2-carboxylate (1200 mg, 4.45 mmol) was dissolved in dry pyridine (21 mL, 0.98 g/mL, 260.17 mmol). l,l,l-trifluoro-2-methylpropan-2- amine (1131.2 mg, 8.9 mmol) was added and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography using gradient elution from heptane to EtOAc (100:0 to 0: 100) yielding ethyl 3- fluoro-l-methyl-4-[(2,2,2-trifluoro-l,l-dimethyl-ethyl)sulfamoyl]pyrrole-2-carboxylate (1.15 g) as a beige powder which was used as such in the next step. Ethyl 3-fluoro-l-methyl-4-[(2,2,2- trifluoro- l,l-dimethyl-ethyl)sulfamoyl]pyrrole-2-carboxylate (0.15 g, 0.42 mmol) and (0863) 4-aminopyridine-2-carbonitrile (54.55 mg, 0.46 mmol) were dissolved in THF (4.1 mL) in a tube. The tube was flushed with nitrogen, capped with a septum and stirred at room temperature. To this was added lithium bis(trimethylsilyl)amide (1.04 mL, 1 M, 1.04 mmol) at once using a syringe. The obtained solution was stirred for 3 hours. Then ammonium chloride (aq. / sat. / 10 mL) was added and the layers where separated. Then it was extracted once using ethyl acetate (10 mL). The combined extracts were concentrated in vacuo and purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The obtained fractions were concentrated in vacuo and repurified by Prep HPLC (RP SunFire Prep CI 8 OmicronBeta-10muiotaeta,30chi150 mm), mobile phase (0.25% NH4HCO3 solution in water, MeOH). The desired fractions were concentrated under reduced pressure and co-evaporated twice with methanol (2 X 20 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 188 (45 mg) as a white powder. Method B: Rt: 0.94 min. m/z: 432.1 (M-H)” Exact mass: 433.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.39 (s, 6 H), 3.83 (s, 3 H), 7.58 (d, J=4.4 Hz, 1 H), 7.91 (dd, J=5.6, 1.9 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H), 8.47 (br. s., 1 H), 8.63 (d, J=5.7 Hz, 1 H), 10.67 (br. s., 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Extracurricular laboratory: Synthetic route of 4-Aminopicolinonitrile

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. 98139-15-2, 4-Aminopicolinonitrile, other downstream synthetic routes, hurry up and to see.

Application of 98139-15-2, Adding some certain compound to certain chemical reactions, such as: 98139-15-2, name is 4-Aminopicolinonitrile,molecular formula is C6H5N3, 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 98139-15-2.

Step One & Two. N-(2-Cyanopyridin-4-yl)-6-hydroxy-2,4-dioxo- 1,2,3,4- tetrahydropyrimidine-5-carboxamide (H3)L_TO a solution of compound C2 (0.713 g, 4.40 mmol) in anhydrous DMSO (2 mL) was added compound HI (0.476 g, 4.00 mmol) at ambient temperature under nitrogen. The reaction mixture was then stirred for 1.5 h to provide a solution of compound H2 in DMSO which was used directly in the subsequent step.

Reference:
Patent; WARRELL, Raymond P.; PIWINSKI, John J.; WO2015/123003; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem