Month: September 2021

Related Products of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 stirred solution of 6-hydroxy-5-iodonicotinic acid (40 g) and DMF (3.51 mL) in toluene (315 mL) was treated dropwise with SOd2 (43.9 mL) at RT and then stirred at 85C for 2.5 h. The solvent was evaporated off under reduced pressure and the residue was redissolved in DCM (315 mL). The solution was cooled in an icy water bath and to this solution a mixture of 4-(chlorodifluoromethoxy)aniline (26 .3 g) and Et3N (63 mL) in DCM (315 mL) was added dropwise. The mixture was stirred at rt for 1 hr. Then a saturated aqueous solution of NaHCO3 was added and the mixture was stirred at rt for 10 mm and a solid was formed. The mixture was then diluted with 315 mL of hexane and filtered to collect the white solid, washed with more water and air dried to afford 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (55.97 g). (Rt = 2.28 mi +ESI m/z: MH+ = 459.0).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Chlorodifluoromethoxy)aniline, its application will become more common.

Reference:
Patent; ASTAR BIOTECH LLC; LI, Lianhai; YU, Chunrong; HUANG, Haihong; (94 pag.)WO2017/186148; (2017); A1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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. HPLC of Formula: C8H17Cl2N

Compound 4 (200mg, 0.75mmol) refluxed with K2CO3 (259.42mg, 1.87mmol), 1-(2-Chloro-ethyl)-azepane hydrochloride (148.58mg, 0.75mmol) in acetone furnished 7 (220mg, 75percent) as brown viscous oil. 1H NMR (300MHz, CDCl3): delta 7.21?7.06 (m, 8H), 6.91?6.78 (m, 3H), 6.64?6.63 (m, 1H), 5.59 (s, 1H), 4.07 (t, J=6.0, 2H), 2.97 (t, J=6.1, 2H), 2.81 (t, J=5.6, 4H), 1.69?1.61 (m, 8H); 13C NMR (CDCl3, 50MHz): delta 157.5, 148.4, 144.1, 136.2, 129.8 (2C), 128.7 (2C), 128.4 (2C), 126.6, 126.5, 126.2, 124.4, 114.4 (2C), 65.7, 57.8, 54.9 (2C), 51.3, 25.7 (3C), 24.1; IR (Neat): 3019, 2938, 2362, 1610, 1509, 1218, 763cm?1; MS (ESI): m/z 392 (M+H)+; Anal. Calcd for C25H29NOS: C, 76.68; H, 7.46; N, 3.58. Found: C, 76.72; H, 7.39; N, 3.61.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26487-67-2, its application will become more common.

Reference:
Article; Singh, Priyanka; Manna, Sudipta Kumar; Jana, Amit Kumar; Saha, Tiash; Mishra, Pankaj; Bera, Saurav; Parai, Maloy Kumar; Srinivas Lavanya Kumar; Mondal, Sankalan; Trivedi, Priyanka; Chaturvedi, Vinita; Singh, Shyam; Sinha, Sudhir; Panda, Gautam; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 357 – 368;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, 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 15205-15-9. 15205-15-9

Step 7: (S) -tert-Butyl (1- (4- ( (2-chloro-6-fluorobenzyl) carbamoyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazol-5-yl) ethyl) carbamate[0525]To 10 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazole-4-carboxylic acid (0.3 g, 0.64 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (183.36 mg, 0.96 mmol) and 1-hydroxy-7-azabenzotriazole (130.56 mg, 0.96 mmol) . To the resulting solution were added (2-chloro-6-fluorophenyl) methanamine (0.1 mL, 0.77 mmol) and N, N-diisopropylethylamine (0.33 mL, 1.92 mmol) , and the mixture was stirred at rt for 22 hours. The reaction mixture was washed with water (20 mL × 3) . The organic layer was dried over anhydrous sodium sulfate. The organic solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 5/1) to give the title compound as a white solid (264 mg, 67) .[0526]1H NMR (400 MHz, CDCl3) : delta ppm 7.59 (dd, J1 8.3 Hz, J2 1.9 Hz, 1H) , 7.54 (d, J 1.8 Hz, 1H) , 7.47 -7.45 (m, 1H) , 7.27 (d, J 4.6 Hz, 1H) , 7.24 (d, J 8.4 Hz, 1H) , 7.10 -7.06 (m, 1H) , 6.71 (t, JF-H 75.0 Hz, 1H) , 5.32 -5.25 (m, 1H) , 4.87 -4.84 (m, 2H) , 3.98 (d, J 6.9 Hz, 2H) , 1.56 (d, J 7.0 Hz, 3H) , 1.45 -1.43 (m, 9H) , 1.38 -1.34 (m, 1H) , 0.73 -0.68 (m, 2H) , 0.44 -0.40 (m, 2H) .

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 2-Chloro-6-fluorobenzylamine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; YU, Tianzhu; ZHANG, Yingjun; ZHANG, Xiangyu; ZHANG, Shiguo; CHENG, Changchung; ZHANG, Jiancun; WO2015/161830; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-(2-Chloroethyl)azepane hydrochloride

Example 2: Synthesis of 2-((2-(azepan-1-yl)ethoxy)methyl)pyrazolo[1 ,5-a]pyridine maleate 0.12 g (3 mmol) of a 60percent NaH suspension in mineral oil were added under nitrogen to a solution of pyrazolo[1 ,5-a]pyridin-2-ylmethanol (100 mg, 0.67 mmol) in 5 mL of dry THF. The mixture was stirred for 5 h at room temperature, and after this time, was added 1 -(2-chloroethyl)azepane hydrochloride (201 mg, 1 .01 mmol) suspended in 8 ml_ of THF with 200muIota of triethylamine (TEA). The mixture was heated at 55 5C for 18 h, allowed to cool to room temperature, quenched with water and extracted with EtOAc, and washed with water. The organic layers were dried over Na2S04 and concentrated under vacuum to afford 0.22 g (65percent) of brown oil. Maleate salt was obtained following the same procedure as for example 1 . 1 H NMR (CDCI3) delta ppm: 8.42 (d, J = 6.8 Hz, 1 H), 7.52 (d, J = 8.8 Hz, 1 H), 7.20 – 7.06 (m, 1 H), 6.78 (t, J = 6.9 Hz, 1 H), 6.49 (s, 1 H), 6.30 (s, 2H), 4.74 (s, 2H), 4.08 – 3.89 (m, 2H), 3.70 – 3.51 (m, 2H), 3.36 – 3.25 (m, 2H), 3.19 – 2.99 (m, 2H), 2.15 – 1 .92 (m, 2H), 1 .92 – 1 .72 (m, 4H), 1 .72 – 1 .54 (m, 2H).

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ FERNANDEZ, Jose Luis; CUBERES ALTISENT, Mª Rosa; WO2013/124341; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 102170-53-6, name is 4-Bromo-5-chloro-2-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. Product Details of 102170-53-6

A 500-mL round-bottom flask was charged with (E)-/er/-butyl 3-(3-methoxy-3-oxoprop-l-en-l-yl)-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate (Preparation 3a, (10.8 g, 26.0 mmol), xantphos (1.88 g, 3.25 mmol), cesium carbonate (25.4 g, 78.0 mmol), 4-bromo-5-chloro-2-methoxyaniline (6.15 g, 26.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.19 g, 1.30 mmol) and 1,4-dioxane (130 mL) then sparged with nitrogen for 15 min. The reaction mixture stirred vigorously for 20 h at ambient temperature. The reaction mixture was subsequently vacuum filtered through a 1.0 cm plug of silica gel and the pad was rinsed with EtOAc (3 x 150 mL). The filtrate was concentrated under reduced pressure to give a brown foam that was used immediately without further purification.[00562] The product was diluted with MeOH (260 mL) and transferred to a 350-mLpressure vessel equipped with a stir bar. The reaction vessel was subsequently charged with sodium methoxide (25 wt. % in MeOH, 2.97 ml, 13.00 mmol) and sealed with a Teflon cap equipped with a pressure-relief valve. The reaction vessel was placed in a 70 C oil bath and stirred vigorously. After 5 h, the reaction mixture was allowed to cool to ambient temperature, transferred to a 1-L round-bottom flask with additional MeOH and concentrated under reduced pressure. The brown oil was redissolved in DCM (150 mL) and filtered through a pad of Celite (3 cm) to facilitate loading the material onto a column. The Celite pad was rinsed with DCM (3 x 50 mL). The brown filtrate was concentrated under reduced pressure and purified by flash column chromatography (340-g Biotage column, eluent: gradient, 5 to 35% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford (Rac)-tert-butyl 1-(4-bromo-5-chloro-2-methoxyphenyl)-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate (9.12 g, 19.4 mmol, 74.7 % yield) as a tan solid.

The synthetic route of 4-Bromo-5-chloro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1939-99-7, name is Phenylmethanesulfonyl chloride, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C7H7ClO2S

A solution of phenylmethanesulfonyl chloride (2.19 g, 10 mmol) was added into a suspension of 3-bromopropan-1-amine hydrobromide (2.19 g, 10 mmol) and Et3N (2.02 g, 20 mmol) in THF (50 mL) at 0 C. The mixture was stirred at 0 C for 5 mi TLC confirmed the completion of reaction. Solid was filtered out with suction, and the filtrate was concentrated to provide compound N-(3-bromopropyl)(phenyl)methanesulfonamide (2.7 g, quant.) as a pale yellow solid which was used in the next step without further purification. ?H NMR (300 MHz, CDC13) oe 7.40 (m, 5H), 4.48 (m, 1H), 4.27 (s, 2H), 3.41 (t, J = 6.6 Hz, 2H), 3.16 (q, 2H), 2.01 (m, 2H). LCMS (ESI), mlz, 314 and 316 [M+Na], Br pattern found.

The synthetic route of 1939-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; RENE, Olivier; WO2014/202741; (2014); A1;,
Chloride – Wikipedia,
Chlorides – 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. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Bromo-2-chloroaniline

Preparation 94 2-Chloro-4-(oxazol-5-yl)aniline Palladium acetate (5.4 mg, 0.024 mmol) was added to a solution of 4-bromo-2-chloroaniline (0.1 g, 0.484 mmol), oxazole (0.064 mL, 0.969 mmol), di(1-adamantyl)-n-butylphosphine (0.017 g, 0.048 mmol), pivalic acid (0.020 g, 0.194 mmol) and potassium carbonate (0.201 g, 1.453 mmol) in DMA (2.4 mL). The reaction mixture was heated at 110 C. overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35 mg, 37%). 1H NMR (500 MHz, CDCl3): delta 4.25 (br s, 2H), 6.82 (d, J=8.3 Hz, 1H), 7.20 (s, 1H), 7.38 (dd, J=8.3, 2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 7.87 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 2.47 min, 195 [(M+H+), 100%].

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; Bavetsias, Vassilios; Atrash, Butrus; Naud, Sebastien Gaston Andre; Sheldrake, Peter William; Blagg, Julian; US2013/345181; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, 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. Application In Synthesis of 4-Bromo-3-chlorobenzene-1,2-diamine

To a solution of 4-bromo-3-chlorobenzene-l,2-diamine (0.15 g) and triethylamine (285 mu.) in DMF (2 mL), 90 mu. of ethyl 2-bromoacetate was added and the reaction mixture was heated at 80 C overnight. After this time, most of the volatiles were removed under reduced pressure and the residue was purified by column chromatography (silica gel, 0-2 % MeOH in DCM) to afford the title compound as a brown solid.

The synthetic route of 4-Bromo-3-chlorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 51114-68-2, 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 51114-68-2 as follows.

A solution of a (15 76 g, 100 mmol, 1.0 eq) in 3M HCI (100 mL) at 0 C was added dropwise a solution ofNaNC (7.59 g, 110 mmol, 1.1 eq) in water (20 mL). The mixture was stirred at 0 C for 30 min, then added to a solution of KI (49.8 g, 300 mmol, 3.0 eq) in water (40 mL). The resulting mixture was stirred at r.t. for 1 h, poured into water (100 mL), and extracted with EtOAc (150 mL x 2). The combined organic layers were washed with sat. NarSCb solution (50 mL x 2) and brine (50 ml, x 2) successively, and then dried with anhydrous NaiSOy filtered, and concentrated. The residue was purified by chromatography on silica gel (PE) to give b (26.0 g, 97%) as red liquid. LCMS: 2.68.9 i M · H | .

According to the analysis of related databases, 51114-68-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SILICON SWAT, INC.; CHAMBERLAIN, Brian T.; RICE, James M.; JERNIGAN, Finith E., III; SHERMAN, Woody; KULKARNI, Meghana M.; SHECHTER, Sharon; ALLEN, Bryce K.; TAN, Dazhi; MARINO, Kristen A.; LIN, Zhixiong; (292 pag.)WO2019/100061; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, belongs to chlorides-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 13918-92-8, Formula: C6H3ClF2O2S

To a cooled (0 C) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (13.7 g, 67.5 mmol) in pyridine (200 ml) was added slowly 2,4-difluorobenzenesulfonyl chloride (14.37 g, 67.6 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h. Most of the pyridine was removed in vacuo and the residue diluted with water (500 ml_). The solids were filtered off and washed with copious amounts of water to give 21 g of crude desired product. More solid appeared in the mother liquor and was filtered and washed with water to give an additional 1.5 g of desired material. The two batches were combined, triturated with 70 ml of methylene chloride, and dried in a vacuum oven at 50 0C to give the title compound (15 g)-LCMS (Method B) R1 = 1.11 min, MH+ = 378/380.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GLAXO GROUP LIMITED; HAMBLIN, Julie, Nicole; HARRISON, Zoe, Alicia; JONES, Paul, Spencer; KEELING, Suzanne, Elaine; LE, Joelle; LUNNISS, Christopher, James; PARR, Nigel, James; WO2010/102958; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics