Category: 1195768-19-4

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. 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate

To a dry three-necked flask, 3- (2,6-difluorophenyl) -2- fluorobenzoate (2.05 g, 5.94 mmol), N, O- dimethylhydroxylamine hydrochloride ( under 743 mg, 7.62 mmol), nitrogen was added distilled tetrahydrofuran (15 mL), and the system was cooled to -15C , slowly dropping 3 M methyl magnesium bromide (9.9 mL), and then the addition was complete 0C transferred to conditions, for 5 hours, quenched with saturated aqueous ammonium chloride added, tetrahydrofuran was removed by rotary evaporation after extraction with ethyl acetate, the solvent was removed by rotary evaporation, the residue was purified by silica gel column chromatography (PE: EA = 10: 1 -1: 2) was isolated as a product (600mg, 31% yield).

The synthetic route of 1195768-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tonghua Jida Pharmaceutical Co., Ltd.; Wu, yongqian; (22 pag.)CN103936728; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1195768-19-4, A common heterocyclic compound, 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, molecular formula is C14H10F3NO4S, 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.

Step B: N-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6- difluorobenzenesulfonamide Methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate (490 g, 1 equiv.), prepared generally in accordance with Step A, above, was dissolved in THF (2.45 L, 5 vols) and stirred and cooled to 0-3 C. 1M lithium bis(trimethylsilyl)amide in THF (5.25 L, 3.7 equiv.) solution was charged to the reaction mixture followed addition of 2- chloro-4-methylpyrimidine (238 g, 1.3 equiv.) in THF (2.45 L, 5 vols). The reaction was then stirred for 1 hr. The reaction was quenched with 4.5M HC1 (3.92 L, 8 vols). The aqueous layer (bootom layer) was removed and discarded. The organic layer was concentrated under reduced pressure to ~2L. IP AC (isopropyl acetate) (2.45L) was added to the reaction mixture which was then concentrated to ~2L. IP AC (0.5L) and MTBE (2.45 L) was added and stirred overnight under N2. The solids were filtered. The solids and mother filtrate added back together and stirred for several hours. The solids were filtered and washed with MTBE (~5 vol). The solids were placed in vacuum oven at 50 C overnight. The solids were dried in vacuum oven at 30 C over weekend to obtain N-{3- [(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (479 g, 72%).

The synthetic route of 1195768-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; GRESHOCK, Joel David; HOOS, Axel; WO2015/87279; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 1195768-19-4,Some common heterocyclic compound, 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, molecular formula is C14H10F3NO4S, 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.

Step D: N-{3-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; In a 1000 mL flask was placed methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate (9.64 g, 27.9 mmol) and THF (200 mL) was added. The flask was placed in an ice/water bath and LiHMDS (90 mL, 90 mmol) was added. 2-Chloro-4-methylpyrimidine (4.5 g, 35.0 mmol) in THF (60 mL) was added dropwise via addition funnel. After the addition was complete, the reaction was allowed to warm to 20 C. over 1 h. The THF volume was reduced to half under reduced pressure and then treated with 6 N HCl. EtOAc was added and the layers were separated. The aqueous layer was extracted twice with EtOAc and the combined organic layer was washed once with brine, dried over NaSO4, and concentrated. The residue was triturated with EtOAc/ether to afford 8.71 g (71%) of the title compound of Step D. MS (ESI): 442 [M+H]+.

The synthetic route of 1195768-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 1195768-19-4, 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 1195768-19-4 as follows.

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, l.OlmL, l.Olmmol) was added to a cooled (0C) solution of Methyl 3-((2,6-difluorophenyl)sulfonamido)-2- fluorobenzoate (lOOmg, 0.29mmol) in THF (2.5mL). After lOmin of stirring, a solution of 4-Methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (76mg, 0.29mmol) in THF (lmL) was slowly added and the reaction mixture was allowed to warm to room temperature. After 2 hours of stirring, saturated aqueous ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (two times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure to afford the title compound (170mg, quant) as a mixture of ketone and enol. LC/MS (ES+): 577.4 (M+l).

According to the analysis of related databases, 1195768-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C14H10F3NO4S

To a dry three-necked flask, 3- (2,6-difluorophenyl) -2- fluorobenzoate (2.05 g, 5.94 mmol), N, O- dimethylhydroxylamine hydrochloride ( under 743 mg, 7.62 mmol), nitrogen was added distilled tetrahydrofuran (15 mL), and the system was cooled to -15C , slowly dropping 3 M methyl magnesium bromide (9.9 mL), and then the addition was complete 0C transferred to conditions, for 5 hours, quenched with saturated aqueous ammonium chloride added, tetrahydrofuran was removed by rotary evaporation after extraction with ethyl acetate, the solvent was removed by rotary evaporation, the residue was purified by silica gel column chromatography (PE: EA = 10: 1 -1: 2) was isolated as a product (600mg, 31% yield).

The synthetic route of 1195768-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tonghua Jida Pharmaceutical Co., Ltd.; Wu, yongqian; (22 pag.)CN103936728; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, 4.05mL, 4.05mmol) was added to a cooled (0C) solution of Methyl 3-((2,6-difluorophenyl)sulfonamido)-2- fluorobenzoate (400mg, 1.16mmol) in THF (3mL). After lOmin of stirring, a solution of 2-chloro-4-methylpyrimidine (178mg, 1.39mmol) in THF (2mL) was slowly added and the reaction mixture was allowed to warm to room temperature for 2h. Aqueous saturated ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (2 times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. Trituration of the brown solid in DCM/cHex afforded title compound (420mg, 82%) as a mixture of ketone and enol. LC/MS (ES+): 442.0-444.0 (M+l).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1195768-19-4.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics