Ethers-buliding-blocks

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 702-24-9 as follows. 702-24-9

3-(5-Amino-2,4-difluorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (2.4 g, 7.5 mmol) and 4-methoxy-N-methylbenzylamine (10 mL) were combined in a sealed vessel and heated to 200¡ã C. overnight. The volatiles were removed in vacuo and the residue was purified by column chromatography to give 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2,4-difluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 91percent yield), which was used in the next step without further purification.

According to the analysis of related databases, 702-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 58-73-1, name is 2-(Benzhydryloxy)-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., 58-73-1

(2) Synthesis of indomethacin-diphenhydramine salt Indomethacin (358 mg, 1 mmol) and diphenhydramine (255 mg, 1 mmol) were stirred at 50 – 60C for 30 min to give an indomethacin-diphenhydramine salt as a yellow starch syrup-like viscous liquid. infrared absorption spectrum (liquid membrane): 1680 cm-1 (amidecarbonyl of indomethacin), 1595 cm-1 (COO-)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Medrx Co., Ltd.; EP2128123; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 366-99-4, name is 3-Fluoro-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. 366-99-4

General procedure: Different aniline (0.75 mmol) was dissolved in CH3CN (10 mL) in a 25-mL round-bottomed flask and cooled to 0¡ãC in an ice bath. To this stirred mixture was added t-BuONO (1.125 mmol) followed by TMSN3 (0.9 mmol) dropwise. The resulting solution was stirred at room temperature for 2 h. Compound 2 (0.5 mmol), CuI(0.1 mmol) and Et3N (0.6 mmol) were then added and the reaction was stirred at room temperature. The progress of the reaction was monitored by TLC. After the completion of reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluting solution to afford the target compounds 3 [25?29]. The data of 3a?3w are shown as follows. We selected one compound, 3d, as a representative compound and signal positions of carbon protons were assigned.

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 366-99-4.

Reference:
Article; Chen, Xiulei; Xiao, Youxin; Wang, Gaolei; Li, Zhong; Xu, Xiaoyong; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5495 – 5508;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding some certain compound to certain chemical reactions, such as: 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, 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 64115-88-4. 64115-88-4

I. Preparation of the intermediatesa. Preparation of sulfonyl chloridesa.1 3-Bromo-4-trifluoromethoxy-benzenesulfonyl chloride2.0 g of 1-bromo-2-(trifluoro-methoxy)benzene (8.3 mmol) were dissolved in 30 ml of dichloromethane. At 0-5C, 1.06 g of chlorosulfonic acid (9.13 mmol), dis- solved in 3 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature. Additional 5.5 equivalents of chlorosulfonic in dichloromethane were added to drive the reaction to completion. Standard work-up was followed and silica gel chromatography with n-heptane- dichloromethane (6:4) as eluent gave 2.19 g of the title compound.1H-NMR (CDCI3, 400 MHz): delta [ppm] 8.3 (d, 1 H), 8.05 (dd, 1 H), 7.5 (dd, 1 H).

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 1-Bromo-2-(trifluoromethoxy)benzene.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2007/118899; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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 95 mg (0.32 mMol) 6-(amino-pyrimidin-4-ylsulfanyl)-naphthalene-1 -carboxylic acid, 85 mg (0.48 mMol) 3-trifluoromethoxy-aniline, 446 mul (3.2 mMol) Et3N and 4 mg (0.03 mMol) DMAP in 3 ml DMF, 0.37 ml (0.63 mMol) propylphosphonic anhydride are added. After 3 h at rt, the reaction mixture is worked up as described for Ex. 58, yielding the title compound: m.p.: 197-199 ¡ãC; MS: [M+1]+= 457.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Trifluoromethoxyaniline, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/31265; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

402-52-8, These common heterocyclic compound, 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, 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.

Example 249A 1-(2-methoxy-5-(trifluoromethyl)phenyl)ethan-1-one A 250 mL 3-neck round bottom flask equipped with a thermometer and an addition funnel was charged with trifluoromethanesulfonic acid (29.6 mL, 333 mmol) and then treated dropwise (?6 drops/minute) under N2 over 3 hours with a mixture of 4-(trifluoromethyl)anisole (11.74 g, 66.6 mmol) and acetic anhydride (12.57 mL, 133 mmol) keeping the internal temperature at or below 30 C. The resulting mixture was stirred at room temperature for 3 hours and then poured carefully into 150 mL of ice water, adding more ice during the addition to prevent the mixture from warming. The mixture was extracted with methyl tert-butyl ether (twice, 150 mL and 50 mL). The combined methyl tert-butyl ether layers were washed with saturated aqueous NaHCO3 solution 4 times (100 mL, 100 mL, 50 mL and 50 mL). The methyl tert-butyl ether layer was washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed on silica gel, eluting with a gradient of 5% to 10% ethyl acetate in heptane to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 8.00 (dd, J=0.8, 2.5 Hz, 1H), 7.70 (ddd, J=0.8, 2.5, 8.8 Hz, 1H), 7.05 (d, J=8.7 Hz, 1H), 3.97 (s, 3H), 2.62 (s, 3H).

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 402-52-8.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (247 pag.)US2018/99932; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-73-5, 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 1535-73-5 as follows.

To a solution of 4-[2-(propargylamino)-2-oxo-acetyl]-1,3,5-trimethyl-pyrrol- 2-carboxylic acid 6 (250 mg, 1.0 mmol), 3-(trifluoromethoxy)aniline (227 mg, 1.3 mmol) and DIPEA (330 muL, 2.0 mmol) in pyridine (10 mL) was added HATU (0.65 g, 1.8 mmol) at room temperature. The mixture was stirred at 65 ¡ãC for 18 h. The reaction mixture was then poured into a saturated solution of ammonium chloride and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (Hexanes:EtOAc = 6:4 v/v) to give compound 55 as a white powder (34percent, 135 mg, 0.3 mmol). 1H NMR (400 MHz, Acetone-d6) delta 9.57 (s, 1H), 8.18 (s, 1H), 8.02 (s, 1H), 7.81? 7.67 (m, 1H), 7.50 (t, J = 8.2 Hz, 1H), 7.16? 7.06 (m, 1H), 4.17 (dd, J = 5.8, 2.6 Hz, 2H), 3.71 (s, 3H), 2.75 (t, J = 2.5 Hz, 1H), 2.45 (s, 3H), 2.32 (s, 3H). MS (ESI): m/z [M+H]+ calcd for C20H19F3N3O4: 422.4, found: 422.4.

According to the analysis of related databases, 3-Trifluoromethoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EMORY UNIVERSITY; SCHINAZI, Raymond F.; BOUCLE, Sebastien; AMBLARD, Franck; SARI, Ozkan; BASSIT, Leda; (169 pag.)WO2017/156255; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

6346-09-4, These common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, 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 stirred solution of 3-formylbenzoic acid (0.50 g, 3.3 mmol) in DMF (7 mL) was added DIPEA (0.61 mL, 3.5 mmol) and HATU (1.5 g, 4.0 mmol) and the mixture stirred at room temperature for 15 minutes. 4,4-Diethoxybutan-l -amine (0.43 g, 2.68 mmol) was added and the- stirring continued for a further five hours. The reaction mixture was diluted and washed sequentially with aqueous 1M sodium hydroxide, aqueous 2M sodium hydroxide and brine. The organic phase was dried over magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford the title compound (0.72 g, 93%). ‘H NMR (400 MHz, DMSO-d6); delta 10.08 (s, 1H), 8.71 (dd, J=5.5, 5.5 Hz, 1H), 8.38 (s, 1H), 8.16 (d, J=7.8 Hz, 1H), 8.06 (d, J=7.7 Hz, 1H), 7.71 (dd, J=7.7, 7.7 Hz, 1H), 4.53 – 4.47 (m, 1H), 3.57 (ddd, J=7.0, 9.5, 14.1 Hz, 2H), 3.43 (ddd, J=7.1, 9.5, 14.1 Hz, 2H), 3.31 – 3.27 (m, 2H), 1.58 – 1.54 (m, 4H), 1.11 (dd, J=7.0, 7.0 Hz, 6H).

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 6346-09-4.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; RIZZI, Andrea; CARZANIGA, Laura; LINNEY, Ian; (108 pag.)WO2017/93208; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

22236-10-8, 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 22236-10-8 as follows.

2-Chloro-N-(4-(difluoromethoxy)phenyl)acetamide (Compound 39): To a solution of 4-(difluoromethoxy)aniline (0.078 ml, 0.628 mmol) and Triethylamine (0.131 ml, 0.943 mmol) in DCM at 0 C., was added 2-chloroacetyl chloride (0.060 ml, 0.754 mmol). The mixture was stirred at RT for 2 h. Solvent was removed and the crude was purified by combiflash chromatography (0-30% EtOAc-Hexanes) to afford 2-chloro-N-(4-(difluoromethoxy)phenyl)acetamide (110 mg, 0.467 mmol, 74.3% yield) as a pale orange solid. 1H-NMR (400 MHz, CDCl3) delta ppm 8.24 (brs, 1H), 7.55 (dd, 2H, J=2 Hz, J=4 Hz), 7.13 (d, 2H, J=8 Hz), 6.48 (t, 1H, J=71.5 Hz), 4.20 (s, 2H); ESI-MS: m/z 235.86 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 22236-10-8, and friends who are interested can also refer to it.

Reference:
Patent; Stingray Therapeutics, Inc.; The University of Utah; Vankayalapati, Hariprasad; Liu, Xiaohui; Ramamoorthy, Gurusankar; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (59 pag.)US2019/31655; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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. 20781-20-8

Intermediate 3C:; [00197] To Intermediate 3B (3.0 g, 11.99 mmol) in toluene (18 mL) was added (2,4-dimethoxyphenyl)methanamine (2.476 mL, 16.48 mmol). The mixture was stirred at 125 0C (oil bath) for 3.5 h. The color changed from deep red to yellow. After the mixture cooled to rt, it was triturated with EtOAc/hexanes (1 : 2) and left standing overnight. The yellow precipitate was collected by filtration to give Intermediate 3C (3.92 g, 96% yield).

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 20781-20-8.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem