Category: 202197-26-0

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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

Step 2) N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-nitroquinazolin-4-amine A mixture of 4-chloro-6-nitroquinazoline (7.50 g, 35.8 mmol) and 3-chloro-4-((3-fluorobenzyl)oxy)aniline (9.00 g, 35.8 mmol) in isopropanol (150 mL) was heated to 80 C and stirred for 3.0 hours. The resulting mixture was then cooled to 20 C, and a yellow solid precipitated out. The mixture was filtered. The filter cake was washed with isopropanol (20 mL) and dried under vacuum to give the title compound as a yellow solid (8.50 g, 59.8%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) m/z : 425.8 [M+l]+; and NMR (400 MHz, CDC13) delta: 11.30 (brs, 1H), 9.54-9.48 (m, 1H), 8.45-8.41 (m, 1H), 8.31-8.25 (m, 1H), 7.98-7.89 (m, 1H), 7.50-7.47 (m, 1H), 7.35-7.26 (m, 1H), 7.05-6.96 (m, 1H), 6.90-6.80 (m, 2H), 7.74-7.60 (m, 2H), 4.84 (s, 2H).

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LIU, Bing; LIU, Jinlei; ZHANG, Jiancun; ZHENG, Changchun; WO2014/177038; (2014); A1;,
Chloride – Wikipedia,
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Reference of 202197-26-0, 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 202197-26-0 as follows.

Compound 12 (1.6 g, 6.28 mmol), commercially available 3-chloro-4-(3-fluorobenzyloxy)aniline 13 (1.6 g, 6.3 mmol) and CH3SO3H (20 muL, 5 mol %) were added into anhydrous EtOH (40 mL) and the reaction mixture was heated at 70 C for 2 h. After cooled down, the alcohol solution was diluted with water (150 mL) and the resulting solid was filtered, washed with water and dried to give N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-iodo-6-methylpyrimidin-4-amine 14 (2.77 g, 94%) as a white solid. MS-ESI (m/z): 467.8(M-H), 470.0(M+H); 1H NMR (CDCl3, delta): 2.65(s, 3H), 5.15(s, 2H), 6.94(d, 1H), 7.02(t, 1H), 7.16(d, 1H), 7.22(d, 1H), 7.35(d, 2H), 7.67(s, 1H), 8.39(s, 1H).

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mao, Yongjun; Zhu, Wenxiu; Kong, Xiaoguang; Wang, Zhen; Xie, Hua; Ding, Jian; Terrett, Nicholas Kenneth; Shen, Jingkang; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3090 – 3104;,
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Chlorides – an overview | ScienceDirect Topics

Electric Literature of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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 6 4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-6-nitro-quinazoline In a flask equipped with a reflux condenser, 6-nitro-4-chloro-quinazoline 1.20g (5.7mmol) and 4-(3-fluorobenzyloxy)-3-chloroaniline 1.37g (5.6mmol) were dissolved into 80mL of isopropanol, and the solution was refluxed for 3h. Then a lot of yellow solid was deposited, which was filtered, dried under vacuum, and identified as the title compound. Yield: 67%. 1H-NMR (400MHz, CDCl3): delta11.30(1H, br), 9.54-9.48(1H, m), 8.45-8.41(1H, m), 8.31-8.25(1H, m), 7.98-7.89(1H, m), 7.50-7.47(1H, m), 7.35-7.26 (1H, m), 7.05-6.96(1H, m), 6.90-6.80(2H, m), 7.74-7.60(2H, m), 4.84(2H, s).

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; SHANGHAI ALLIST PHARMACEUTICAL., INC.; EP1990337; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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.

General procedure: To a 50-ml glass round-bottom flask was added sequentially the primary amine 2 (1.0 mmol; aliphatic, aromatic or heteroaromatic; as free naked amine or as HCl, MsOH, TsOH or tartrate salt), FSO2N3 solution (containing 1.0 mmol FSO2N3, approximately 200 mM in DMF/MTBE 1:1, v/v, approximately 5 ml, volume adjusted according to the concentration; prepared according to the above procedure and diluted with equal volume of DMF) and aqueous KHCO3 solution (3.0 M, 1.33 ml, containing 4.0 mmol KHCO3). The reaction mixture was stirred for 5 min at room temperature, while monitoring by LC-MS. After completion, EtOAc (40 ml) was added and the mixture was washed sequentially with brine (60 ml × 6), water (60 ml × 2) and brine (60 ml), dried over Na2SO4, concentrated by rotary evaporation and dried under vacuum to afford the azide product 3. For products containing acidic functional groups, this extraction process was modified with acidified aqueous phase (acidified with aqueous HCl). Detailed procedures and the various modifications, as well as the characterization data for each compound, can be found in Supplementary Information 1.

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:
Article; Meng, Genyi; Guo, Taijie; Ma, Tiancheng; Zhang, Jiong; Shen, Yucheng; Sharpless, Karl Barry; Dong, Jiajia; Nature; vol. 574; 7776; (2019); p. 86 – 89;,
Chloride – Wikipedia,
Chlorides – 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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

(iii) Preparation of N-[3-chIoro-4-[(3-fluorobenzyIoxy)phenyl]-6-iodo- quinazolin amine (3) Into a one liter four-necked round bottomed flask, 500mL of acetic acid, 50.0 g of N’- (2-cyano-4-iodo-phenyl)-N, N-dimethyl formamidine of the formula-(8) obtained according to the process given in the above step (ii) 51.0 g 3-chloro-4-(3′- fluorobenzyloxy)aniline were charged . The reaction mass was maintained at 115- 120 C for about 2 Hrs., the cooled to 25-35 C and quenched into ice cold water. The pH of the reaction mass was adjusted to basic by slow addition of aqueous ammonia solution and the reaction mass was filtered and dried at 70-75 C.Dry weight: 93.0 gPurity: 83.64% by HPLCThe purity of the product is enhanced by adopting the following procedure.

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; JYOTHI PRASAD, Ramanadham; ADIBHATLA KALI SATYA, Bhujanga rao; VENKAIAH CHOWDARY, Nannapaneni; WO2011/39759; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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. Recommanded Product: 202197-26-0

The 3.2g (12.7mmol) compound (VI compound of formula) and 6.4g (53.7mmol) DMF-DMA was added to 100mL eggplant Bottle, heated to reflux for 1h, evaporated under reduced pressure to remove excess DMF-DMA; glacial acetic acid was added 20mL (349.4mmol) and 3.4g (10.7mmol) 2-amino-5-[5-[[[2-(methanesulfonyl)ethyl]amino]methyl]furan-2-yl]benzonitrile (V), was heated under reflux IH; After the reaction system was cooled to room temperature and poured into 80mL of ice water, suction filtered, the filter cake washed with 80mL of methanol and 80mL of ice water Di, 60 C vacuum drying 8h, give lapatinib (a compound of Formula I) 5.1g (8.8mmol, molar yield of 82.4%, HPLC pure Of 99.3%).

The synthetic route of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI ACEBRIGHT PHARMACEUTICAL CO., LTD; DAFENG ACEBRIGHT PHARMACEUTICALS CO., LTD; SHANGHAI ACEBRIGHT PHARMACEUTICALS GROUP CO., LTD.; AN, XIAOXIA; LYU, FENG; YAN, LI; WANG, GUANXING; GAI, HONGTAO; LI, HUICHAO; (12 pag.)CN103896889; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 202197-26-0 as follows. Safety of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

To 2-propanol (300 mL) were sequentially added 4-chloro-5,8-dihydro-6H-spiro[l- benzothieno[2,3-d]pyrimidme-7,2′-[l,3]dioxolane] (20.7 g, 73.2 mmol), 3-Chloro-4-(3- fluoro-benzyloxy)-phenylamine (18.4 g, 73.2 mmol), and HCl in dioxane (4N, 0.92 mL). The suspension was stirred with heating to 80 0C, upon which the contents turn brown and homogeneous. After 15 h, the dark orange-yellow heterogeneous mixture was removed from heating, and allowed to cool to rt. The contents were filtered and the collected solid product dried under vacuum. The filtrate was concentrated under reduced pressure and the EPO residue suspended in CH3OH (50 niL), upon which formation of a second crop of product ensues. The second crop was collected, and from this filtrate a third crop could also be obtained. The solid product crops were combined to afford the final product (33.5 g, 92%) as an off-white solid. 1H-NMR delta 1.90 (t, 2H), 3.00 (s, 2H), 3.26 (t, 2H), 3.97 (s, 4H), 5.22 (s, 2H), 7.11-7.30 (m, 4H), 7.41-7.55 (m, 2H), 7.74 (s, IH), 8.33 (s, IH), 8.39 (s, IH); LCMS RT = 3.63 min; [M+H]+ = 498.3.

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/55268; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This 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.

Roschangar et al. ,Use of lithium N,O-dimethylhydroxylamide as an efficient in situ protecting agent for aromatic aldehydes. Tertrahedron 2002, 58, 1657-1666). Preparation analogous (Nishino et al.; Process for producing 4-aminoquinazoline compound by chlorination of quinazolin-4-one or its derivative and animation. 2003) as follows: To a mixture of 6-iodo-lH-quinazolin-4-one (10) (6.8Og; 25.0 mmol), toluene (5.0 mL) and POCl3 (27.5 mmol; 2.60 mL) carefully triethylamine (27.5 mmol; 3.81 mL) was added. The mixture was heated to 80 0C for 2 h, cooled to room temperature, a solution of 3-chloro~4-(3- fluorobenzyloxy)phenylamine (15) (27.50 mmol; 6.92 g) in 2~butanone (20.0 mL) added and the mixture stirred at 80 0C for another hour. The mixture was cooled to 00C, the yellow precipitate was filtered off and added to a NaOH solution (IN; 150 mL) by stirring. After 30 min the yellow solid was filtered off, washed with water and a small amount of acetone and dried in vacuo. Yield (8.38 g; 66%) analytical pure sample. 1H-NMR (DMSO-[D6]): delta (ppm) = 5.26 (s, 2H), 7.15-7.22 (m, IH), 7.27 (d, IH, J = 9.1 Hz), 7.29-7.35 (m, 2H), 7.43-7.51 (m, IH), 7.56 (d, IH, J = 8.8 Hz), 7.74 (dd, IH, J = 9.1 Hz, 4J = 2.5 Hz), 8.02 (d, IH5 4J = 2.5 Hz), 8.12 (dd; IH, J = 8.8 Hz, 4J = 1.7 Hz)5 8.62 (s, IH), 8.96 (d, 4J = 1.7 Hz), 9.90 (s, IH, exchangeable).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; 4SC AG; WO2009/63054; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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 round bottle, isopropanol (20 mL), 3-bromoaniline (0.62 g, 3.6 mmol), 4-cholo-6-iodo-quinazoline 15 (0.87 g, 3 mmol) andtriethylamine (0.36 g, 3.6 mmol) was added. The resulting reactionmixture was stirred at room temperature for 6 h and then at refluxfor another 3 h. After cooling to room temperature, the yellow solidwas collected by suck filtration, wash with isopropanol, water andether sequentially, and dried at 50 C to afford compound 12a as ayellow solid (0.74 g, 69% yield)

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Songwen; Li, Yingbo; Zheng, Yufen; Luo, Laichun; Sun, Qi; Ge, Zemei; Cheng, Tieming; Li, Runtao; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 442 – 458;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This 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.

General procedure: Followed we described previously, substituted aniline (3.3 mol). The reaction mixture was heated to 130 and stirred for 15 min. The reaction mixture was then cooled to 25 . The acetic acid was evaporated. The reaction mixture was quenched in ice-water (25.0 mL), and adjusted pH~9 with ammonia solution. The mixture was stirred for 0.5 h. The precipitated product was filtered, and the filter cake was washed with water (3 × 10 mL) to afford crude product. The crude product was chromatographed by silica gel, eluting with EtOAc/PE (1:4) to afford residue 13a-13c as white solid (yield 84.3% ~ 92.5%). 1.2.1.1 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-iodoquinazoline (13a) White power, yield: 92.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Yaling; Gao, Hongliang; Liu, Renjie; Liu, Juan; Chen, Li; Li, Xiabing; Zhao, Lijun; Wang, Wei; Li, Baolin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4309 – 4313;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics