Category: 363-47-3

A common compound: 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 363-47-3

Example 19 N-(3,5-difluoro-4-methoxyphenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0299) To a mixture of 3,5-difluoro-4-methoxyaniline (54 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (46 mg). 1H NMR (300 MHz, DMSO-d6) delta3.86 (3H, s), 4.15 (2H, s), 6.88 (1H, d, J = 6.8 Hz), 7.25 (1H, dd, J = 9.0, 6.8 Hz), 7.35 (2H, d, J = 10.5 Hz), 7.55 (1H, d, J = 9.0 Hz), 7.62 (1H, d, J = 1.1 Hz), 7.85 (1H, s), 10.66 (1H, 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, 363-47-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 363-47-3,Some common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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: The relevant halogenated heterocycle (1.0equiv.), substituted aniline (2.0 equiv.) and TFA (5.0 equiv.) were takenup in TFE (0.1 M) and heated under microwave irradiation conditionsat 140 C for 30 min before being concentrated in vacuo. The residuewas resuspended in EtOAc:THF (1:1, 20 mL/mmol), washed with saturatedNaHCO3 solution (20 mL/mmol), and the aqueous phase wasfurther extracted with EtOAc:THF (1:1, 3 × 15 mL/mmol). The combinedorganic extracts were washed with brine, dried (MgSO4) andconcentrated in vacuo. The resultant residue was purified via columnchromatography and/or triturated as specified to afford the desired compound.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Casalvieri, Kimberly A.; Matheson, Christopher J.; Backos, Donald S.; Reigan, Philip; Bioorganic and Medicinal Chemistry; vol. 28; 5; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 363-47-3, A common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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.

A solution of 3,5-difluoro-4-methoxyaniline (100 mg, 0.628 mmol) and triethylamine (131 mul, 0.943 mmol) in DCM was coiled and added 2-chloroacetyl chloride (60.0 mul, 0.754 mmol). The reaction mixture was stirred at room temperature for 2 h. Reaction was diluted with DCM, washed with 0.5 M HCl, water, brine, dried over Na2SO4 and evaporated. The crude brown solid, 2-chloro-N-(3,5-difluoro-4-methoxyphenyl)acetamide (120 mg, 0.509 mmol, 81% yield) was used for the next step without purification. 1H-NMR (400 MHz, CDCl3) delta ppm 8.15 (s, 1H), 7.21 (d, 1H, J=8 Hz), 4.18 (s, 1H), 3.97 (s, 3H); ESI-MS: m/z 235.82 (M+H)+.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Stingray Therapeutics, Inc.; Vankayalapati, Hariprasad; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (117 pag.)US2020/39979; (2020); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 363-47-3, These common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, 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 glacial acetic acid (4.0 mL) precooled to 5 C were added potassium thiocyanate (4.0 mmol) and 2,6-difluoro-p-anisidine (1) (1.0 mmol). The mixture was stirred vigorously while 1.1 mmol of bromine in 1.5 mL of glacial acetic acid was added drop-wise such that the temperature did not rise beyond 0 C. After all the bromine was added (60 min), the solution was stirred for another 2 h at 0 C and at ambient temperature for 10 h. It was allowed to stand overnight, during which a yellowish-orange precipitate settled out. Water (30 mL) was added and the solution was adjusted to pH 6 with sat aq NaHCO3. The mixture was extracted with dichloromethane (3 × 50 mL) and the combined extracts were dried over Na2SO4 and evaporated to give a yellowish-orange solid as the crude product. Flash chromatography using hexane:dichloromethane 2:3 gave a dark yellow solid in 56% yield.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pirrung, Michael C.; Biswas, Goutam; De Howitt, Natalie; Liao, Jiayu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 20; (2014); p. 4881 – 4883;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 363-47-3

Example 19 N-(3,5-difluoro-4-methoxyphenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0299) To a mixture of 3,5-difluoro-4-methoxyaniline (54 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (46 mg). 1H NMR (300 MHz, DMSO-d6) delta3.86 (3H, s), 4.15 (2H, s), 6.88 (1H, d, J = 6.8 Hz), 7.25 (1H, dd, J = 9.0, 6.8 Hz), 7.35 (2H, d, J = 10.5 Hz), 7.55 (1H, d, J = 9.0 Hz), 7.62 (1H, d, J = 1.1 Hz), 7.85 (1H, s), 10.66 (1H, 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, 363-47-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem