Category: 143879-78-1

Synthetic Route of 143879-78-1, These common heterocyclic compound, 143879-78-1, name is 3-Amino-2,6-difluorobenzonitrile, 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.

Methyl (3 S)-3 ,7-dimethyl- 1,1 -dioxo-2,3 ,4,5 -tetrahydropyrrolo [3 ,4-f]thiazepine-6- carboxylate (200 mg, 0.73 mmol) and 3-amino-2,6-difluoro-benzonitrile (0.16 g, 0.88 mmol) in dry THF (5 mL) was treated with lithium bis(trimethylsilyl)amide (2.2 mL, 1 M in THF, 2.2 mmol) and this was stirred overnight at room temperature. Theresulting mixture was quenched with NH4C1 (aq., sat., 5 mL). Then 5 mL of brine wasadded and the layers were separated. The water layer was extracted using EtOAc (2 X30 mL). The combined extracts were concentrated in vacuo and the obtained crude waspurified using silica gel column chromatography (gradient elution: EtOAc:heptane0:100 to 100:0). The desired fractions were concentrated in vacuo and the obtainedresidue was purified via preparative HPLC (Stationary phase: RP XBridge Prep C18 OBD-l0jim, 3OxlSOmm, Mobile phase: 0.25% NH4HCO3 solution in water, ACN). The desired fractions were concentrated under reduced pressure, co-evaporated with methanol (2 X 25 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 157 (7.6 mg). ?H NMR (400 MHz, DMSO-d6) oe ppm 1.14 (d, J=6.82 Hz,3H)1.31-1.45(m,1H)1.81-1.91(m,1H)2.77-2.89(m,1H)3.07-3.18(m,1H)3.58 – 3.67 (m, 1 H) 3.70 (s, 3 H) 7.03 (d, J=9.68 Hz, 1 H) 7.40 – 7.51 (m, 2 H) 8.06(td,J=8.97, 6.05 Hz, 1 H) 10.31 (s, 1 H); Method B; Rt: 0.85 mi mlz :393 (M-H)Exact mass: 394.1, MP: 247.5 C.

The synthetic route of 143879-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VENDEVILLE, Sandrine, Marie, Helene; LAST, Stefaan, Julien; DEMIN, Samuel, Dominique; GROSSE, Sandrine, Celine; HACHE, Geerwin, Yvonne, Paul; HU, Lili; PIETERS, Serge, Maria, Aloysius; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; (244 pag.)WO2017/1655; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 143879-78-1, name is 3-Amino-2,6-difluorobenzonitrile, belongs to nitriles-buliding-blocks compound, 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 143879-78-1, Computed Properties of C7H4F2N2

Example 4: 2,6-Difluoro-3-[5-(3-morpholin-4-ylphenoxy)-pyrimidin-2-ylamino]- benzonitrileA suspension of 4-[3-(2-chloro-pyrimidin-5-yloxy)phenyl]morpholine (180mg, 0.619 mmol), 3-amino-2,6-difluorobenzonitrile (95.3mg, 0.619mmol), ira(dibenzylidene- acetone)palladium(O) (28.3mg, 0.030mmol), 4,5-bis,(diphenylphosphino)-9,9- dimethyl-xanthene (35.8mg, 0.061mmol) and cesium carbonate (403mg, 1.238mmol) in degassed 1,4-dioxane (4mL) was heated at 80C for 2 days. The suspension was diluted with ethyl acetate and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (ethyl acetate:hexane, 1: 1) to afford 2,6-difluoro-3-[5-(3-morpholin-4-ylphenoxy)pyrimidin-2-ylamino]benzonitrile as a solid (l lOmg, 44%).Mass: (ES+) 410 (M+H)+ HPLC: 99.2%NMR: deltaEta ( 6-DMSO) 3.08 (4H, m), 3.69 (4H, m), 6.34 (IH, dd), 6.60 (IH, br s), 6.69 (IH, dd), 7.18 (IH, t), 7.40 (IH, t), 8.10 (IH, m), 8.35 (2H, s) and 9.59 (IH, s).

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, 3-Amino-2,6-difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David; SCOPES, David; WO2011/144577; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 143879-78-1, These common heterocyclic compound, 143879-78-1, name is 3-Amino-2,6-difluorobenzonitrile, 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.

Methyl (3 S)-3 ,7-dimethyl- 1,1 -dioxo-2,3 ,4,5 -tetrahydropyrrolo [3 ,4-f]thiazepine-6- carboxylate (200 mg, 0.73 mmol) and 3-amino-2,6-difluoro-benzonitrile (0.16 g, 0.88 mmol) in dry THF (5 mL) was treated with lithium bis(trimethylsilyl)amide (2.2 mL, 1 M in THF, 2.2 mmol) and this was stirred overnight at room temperature. Theresulting mixture was quenched with NH4C1 (aq., sat., 5 mL). Then 5 mL of brine wasadded and the layers were separated. The water layer was extracted using EtOAc (2 X30 mL). The combined extracts were concentrated in vacuo and the obtained crude waspurified using silica gel column chromatography (gradient elution: EtOAc:heptane0:100 to 100:0). The desired fractions were concentrated in vacuo and the obtainedresidue was purified via preparative HPLC (Stationary phase: RP XBridge Prep C18 OBD-l0jim, 3OxlSOmm, Mobile phase: 0.25% NH4HCO3 solution in water, ACN). The desired fractions were concentrated under reduced pressure, co-evaporated with methanol (2 X 25 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 157 (7.6 mg). ?H NMR (400 MHz, DMSO-d6) oe ppm 1.14 (d, J=6.82 Hz,3H)1.31-1.45(m,1H)1.81-1.91(m,1H)2.77-2.89(m,1H)3.07-3.18(m,1H)3.58 – 3.67 (m, 1 H) 3.70 (s, 3 H) 7.03 (d, J=9.68 Hz, 1 H) 7.40 – 7.51 (m, 2 H) 8.06(td,J=8.97, 6.05 Hz, 1 H) 10.31 (s, 1 H); Method B; Rt: 0.85 mi mlz :393 (M-H)Exact mass: 394.1, MP: 247.5 C.

The synthetic route of 143879-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VENDEVILLE, Sandrine, Marie, Helene; LAST, Stefaan, Julien; DEMIN, Samuel, Dominique; GROSSE, Sandrine, Celine; HACHE, Geerwin, Yvonne, Paul; HU, Lili; PIETERS, Serge, Maria, Aloysius; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; (244 pag.)WO2017/1655; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 143879-78-1, 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 143879-78-1 as follows.

Methyl 1 -methyl-4-[ [(1 S)-2,2,2-trifluoro- i-methyl-ethyl] sulfamoyl]pyrrole-2-carboxylate (0.7 g, 2.23 mmol) was dissolved in THF (10 mL) under nitrogen. To this was added 3-amino-2,6- difluorobenzonitrile (0.45 g, 2.9 mmol) and the mixture was cooled in an ice-water bath while stirred under nitrogen. To this was added drop wise lithium bis(trimethylsilyl)amide 1M intoluene (6.68 mL, 6.68 mmol) over a period of 10 minutes. The resulting mixture was stirred for1 hour while cooling was continued. The mixture was quenched with saturated ammonium chloride (25 mL) and the resulting mixture was extracted using EtOAc (3 x 25 mL). The combined extracts were washed with brine (20 mL), dried on Na2SO4, filtered and concentrated in vacuo. The obtained residue was dissolved in 2 mL dichloromethane and this was loaded on a dry silica plug. This was purified by column chromatography using gradient elution fromheptane to EtOAc. (100:0 to 0:100). The desired fractions were collected and concentrated in vacuo yielding a powder. This powder was recrystallized out of MeOH/water. The obtained crystals were collected on a filter, rinsed with water followed by diisopropylether and dried in a vacuo at 55C for 24 hours resulting in N-(3-Cyano-2,4-difluorophenyl)-1-methyl-4-{[(1S)- 2,2,2-trifluoro- 1 -methylethyl] sulfamoyl} -1 H-pyrrole-2-carboxamide (563 mg) as a powder.Method A: Rt: 1.75 mm mlz: 435.0 (M-H) Exact mass: 436.06. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.09 (d, J=6.8 Hz, 3 H), 3.80 – 4.06 (m, 4 H), 7.36 (d, J2.0 Hz, 1 H), 7.40 – 7.51 (m, 1 H), 7.66 (d, J=1.5 Hz, 1 H), 7.85 – 8.02 (m, 1 H), 8.54 (br. s, 1 H), 10.14 (br. s, 1 H).

According to the analysis of related databases, 143879-78-1, the application of this compound in the production field has become more and more popular.