Tag: M.W=100-200

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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 1-(2-Chloroethyl)azepane hydrochloride

To a solution of 1,1-bis(4-hydroxyphenyl)but-1-ene (80.0 mg, 0.333 mmol) in DMF (3.33 mL) at 0 °C was added 60percent sodium hydride (dispersion in paraffin liquid, 79.9 mg, 2.00 mmol). The reaction mixture was stirred for 15 min at 50 °C and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (216 mg, 1.09 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 3 h at 50 °C, saturated aqueous ammonium chloride was added at 0 °C. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 9/1) to afford RID-F-S*2 (compound 22) (130 mg, 80percent) as an orange oil

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; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
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2687-12-9, name is Cinnamyl 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. Application In Synthesis of Cinnamyl chloride

General procedure: Briefly, a mixture of alkylimidazoles such as 1-methyl-1H-imidazole (MIM), 1-hexyl-1H-imidazole(HIM), 1-octyl-1H-imidazole (OIM), and 1-decyl-1H-imidazole (DIM) (1 mmol), as well as cinnamylchloride (1 mmol) solvent-free were microwaved to 200 MW at 80 C for 5 min (optimumreaction condition). Reaction completion was marked by separation of dense IL. Products suchas 1-methyl-3-cinnamylimidazolium chloride [CMIM]Cl, 1-hexyl-3-cinnamylimidazolium chloride[CHIM]Cl, 1-octyl-3-cinnamylimidazolium chloride [COIM]Cl, and 1-decyl-3-cinnamylimidazolium chloride [CDIM]Cl were isolated by decanting toluene to remove any unreacted starting materialsand solvents. Subsequently, ILs were rinsed with diethyl ether (4 10 mL) separating afterward thislatter layer by decantation. In each case, ILs were finally dried under reduced pressure to get rid of thevolatile organic compounds.

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Doria, Oscar Forero; Castro, Ricardo; Gutierrez, Margarita; Valenzuela, Diego Gonzalez; Santos, Leonardo; Ramirez, David; Guzman, Luis; Molecules; vol. 23; 9; (2018);,
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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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5ClFN

[00387] Intermediate 32A. (E)-N’-(3-Chloro-2-fluorophenyl)-2- oxopropanehydrazonoyl chloride: To a solution of 3-chloro-2-fluoroaniline (1.511 mL, 13.74 mmol) in HCl (116 mL, 116 mmol) at 0 C was added a solution of sodium nitrite (1.896 g, 27.5 mmol) in water (12 mL) dropwise while maintaining the temperature at 0 C. After completion of addition, the reaction was stirred at the same temperature for additional 30 mins. The pH of the reaction mixture was adjusted to 4.5 using solid sodium acetate. The resultant mixture was then treated dropwise with 3-chloropentane- 2,4-dione (2.129 mL, 17.86 mmol) in methanol (12 mL). After completion of addition, the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with water and then extracted with ether. The crude product was then purified by silica gel chromatography to isolate the desired product. MS(ESI) m/z: 249.0 (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 2106-04-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
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4152-90-3, name is (3-Chlorophenyl)methanamine, 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. Computed Properties of C7H8ClN

A solution of 8-chloro-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-[1,2,4]triazolo[4, 3-a]pyrazine (500 mg, 1.60 mmol), (3-chlorophenyl)methanamine (0.39 mL, 3.2 mmol) and TEA (0.68 mL, 4.8 mmol) in EtOH (8.0 mL) was stirred at 80° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with DCM and washed with water and brine. The separated organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by MPLC on SiO2 (2-5percent MeOH in DCM) to give N-(3-chlorobenzyl)-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-[1,2,4]triazolo[4,3-a]pyrazin-8-amine (2.40 g, 90percent) as a yellow oil. 1H-NMR (CDCl3, 400 MHz): delta 7.41 (m, 2H), 7.27 (m, 3H), 7.24 (d, J=4.8 Hz, 1H), 5.75 (d, J=5.2 Hz, 1H), 5.31 (t, J=4.0 Hz, 1H), 4.62 (s, 1H), 2.95 (m, 2H), 1.59 (s, 3H), 1.42 (s, 3H).

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANDOK INC.; Lee, Jin-Hwa; Kim, Seung-Yong; Kim, Do-Ran; Ahn, Koo-Hyeon; Lee, Gwi-Bin; Kim, Doo-Seop; Hwang, Hyun-Sook; (74 pag.)US2017/204101; (2017); A1;,
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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 1939-99-7 as follows. Recommanded Product: 1939-99-7

Example 95 Preparation of t-Butyl (3-Benzylsufonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetate STR115 Collidine (0.59 mL, 4.5 mmole) was added in one portion to a stirred solution of the compound of Example 94 (0.89 g, 3.7 mmole) and benzylsulfonyl chloride (0.86 g, 4.5 mmole) in acetonitrile (20 ml) cooled in an ice bath. The solution was stirred for 5 minutes at 0 C., followed by 45 min at room temperature. The reaction mixture was quenched with water, then diluted with ethyl acetate (100 mL), washed with 3% HCl (until aqueous layer is pH 1), and brine, dried over magnesium sulfate, and the solvent was removed. The residue was dissolved in methanol, concentrated to a volume of approximately 3 mL, and the product was precipitated with the addition of diethyl ether. The precipitate was filtered to give 0.67 g of the title compound. The filtrate was concentrated and chromatographed on flash silica gel using 20-67% ethyl acetate hexanes as eluent. An additional 0.20 g of the title compound was recovered. A total of 0.87 g of the title compound (59% yield) was recovered. Rf=0.29 (silica gel, 33% ethyl acetate/hexanes).

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corvas International, Inc.; US5658930; (1997); A;,
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Synthetic Route of 108-37-2, 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. 108-37-2, name is 1-Bromo-3-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (76 mL, 0.4 mol) in anhydrous THF (664 mL) and n-hexane (220 mL) was added 2.5 M n-BuLi (160 mL, 0.4 mol) dropwise at -78 0C over 1 h. The mixture was stirred for 1 h at -78 0C and a solution of 1-bromo- 3-chlorobenzene (76 g, 0.4 mol) in anhydrous THF (300 mL) was added dropwise at – 78 0C. After stirring for an additional 1 h at the same temperature, a solution of iodine (101 g, 0.4 mol) in anhydrous THF (400 mL) was added dropwise at -78 0C. The temperature was raised from -78 0C to rt during 2 h. After stirring for 18 h at rt, the mixture was concentrated in vacuo to give the crude product (120 g) which was distilled under reduced pressure to give l-bromo-3-fluoro-2-iodobenzene (115 g, 91%). 1H NMR (400MHz, CDCl3): 7.12-7.18 (t, IH), 7.35-7.41 (dd, IH), 7.49-7.54 (dd, IH); MS (E/Z): 317 (M+H+)

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.; WO2008/124575; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1005-56-7,Some common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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.

95) 8-Bromo-2′-phenoxythiocarbonyladenosine-3′,5′-cyclic boranophosphate, Sp- isomer (Sp-8-Br-2′-PTC-cAMPB. No. 306)A solution of 5 muiotatauiotaomicronIota of Sp-8-Br-cAMPB (example 2) in 2 ml of dry dichloromethane was treated with 2.5 mg of dimethylaminopyridine (Aldrich) and 1 .4 muIota of phenoxythiocarbonyl chloride (Fluka) for 16 h at RT under argon. The decrease of the starting material at 1 :62 min was followed by HPLC (RP-18, 20 Vol.-% acetonitrile, 20 mM triethylammonium formate buffer, 1 .5 ml/min., pH 7 at 259 nm).The peak for Sp-8-Br-2′-PTC-cAMPB at 2:69 min was isolated by semipreparative column chromatography on reversed phase silica (RP-18, 40 Vol.-% acetonitrile, 20 mM triethylammonium formate buffer, 1 .5 ml/min., pH 7), yield 87.6%.C17H18BBrN506PS; MW 542.1 1 UV: max: 259 nm HPLC: 2:69 min.ESI-MS (+): m/z 643/645 [M + 2TEA + H] +^ 629 [M + 2TEA – BH3 + H] + ESI-MS (-): m/z 540/542 [M – H]? 526 [M – BH3 – H] ~ ^ 212 [8-Br-A – H] +

The synthetic route of 1005-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLOG LIFE SCIENCE INSTITUTE FORSCHUNGSLABOR UND BIOCHEMICA-VERTRIEB GMBH; GENIESER, Hans-Gottfried; WO2012/130829; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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 104-11-0, Recommanded Product: 1-(4-Chlorophenyl)-N-methylmethanamine

In a 25 mL single neck round-bottomed flask, the intermediate 4 (1 g, 3.35 mmol) from Example 1 and N-(4-chlorobenzyl)-N-methylamine (2.6 g, 16.7 mmol) were added and the mixture was heated to 120 C for 24 h. Reaction was monitored by TLC to completion and was added 10 mL water followed by acidification with dil. HCl to pH 3-4. The mixture was extracted with EtOAc (3 X 50 mL) and the combined organic layer was dried over Na2S04. The sovent was evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (silica gel) to provide the desired product, 7-((4-chlorobenzyl)(methyl)amino)-6-fluoro-l-isobutyl-4-oxo-l ,4-dihydroquinoline-3- carboxylic acid (5), 50 mg; Yield (3.5 %); H NMR (400 MHz, OMSO-de) : delta 15.44 (s, 1H), 6.84-8.70 (m, 7H), 4.66 (s, 2H), 4.24-4.25 (d, 2H), 3.14 (s, 3H), 1.81-1.87 (m, 1H), 0.75-0.77 (d, 6H); MS (ESI): 417.2(M+H); HPLC: 96.35 %.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Chlorophenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; NIROGYONE THERAPEUTICS, INC.; SANDANAYAKA, Vincent; WU, Qiong; (80 pag.)WO2016/81464; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, 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. Quality Control of 2-(3-Chlorophenyl)ethanamine

2-(1-isopropyl-6-oxo-3-(pyridin-2-yl)piperidin-3-yl)acetaldehyde44B (0.15 g, 0.58 mmol) was dissolved in dichloromethane (10 mL).(3-chlorobenzyl)methylamine is sequentially added thereto(0.098g, 0.69mmol), triethylamine(0.070 g, 0.69 mmol), anhydrous sodium sulfate (0.56 g).After reacting at room temperature overnight, sodium borohydride (0.035 g, 0.86 mmol) was added.Stirring was continued for 2 h, water (20 mL) was added andEtOAc was appliedThe organic phases were combined and washed with a saturated aqueous solution of brine (30 mL×1).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate.Column chromatography (dichloromethane/methanol = 30:1)Light yellow oily product 5-(2-((3-chlorobenzyl)amino)ethyl)-1-isopropyl-5-(pyridin-2-yl)piperidin-2-one (45A)(0.085 g, 45%).

The synthetic route of 2-(3-Chlorophenyl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Zhu Fengfei; Chen Qingping; Wang Chengtao; (251 pag.)CN109206417; (2019); A;,
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Synthetic Route of 821-10-3, 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. 821-10-3, name is 1,4-Dichlorobut-2-yne belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1,4-Dichloro-2-butyne (6 mmol, 0.58 mL) was added to the stirred suspension of potassium phthalimide (3 mmol, 0.556 g) in DMF (5 mL), and heated to 100 C for 5 h. After cooling, the reaction mixture was extracted with dichloromethane and water. The organic layers were pooled, dried, and concentrated in vacuo. The residue was purified by column chromatography (hexane/ethyl acetate 1:19) to furnish 0.35 g of 2-(4-chlorobut-2-ynyl)isoindoline-1,3-dione (28) (white solid, yield 50%). 1H NMR (300 MHz, CDCl3) 4.11 (s, 2H), 4.51 (s, 2H), 7.75 (dd, J1 = 3.1, J2 = 5.5, 2H), 7.89 (dd, J1 = 3.1, J2 = 5.4, 2H).13C NMR (75 MHz, CDCl3) delta 27.1, 45.7, 46.9, 51.7 (2C), 54.7 (2C), 78.1, 78.4, 123.4 (2C), 131.9 (2C), 134.0 (2C), 166.9 (2C). 28 was reacted with 1-methylpiperazine following the method described in Section 6.6. to give 2-(4-(4-methylpiperazin-1-yl)but-2-ynyl)isoindoline-1,3-dione (29): A solution of 29 (0.72 mmol, 0.213 g) and hydrazine (0.72 mmol, 0.03 mL) in 1 mL of ethanol was heated at reflux for 2 h. After cooling to 0 C, phthalhydrazide was removed by filtration. Evaporation of the filtrate gave 30 as a free base.

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, 1,4-Dichlorobut-2-yne, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nguyen, Thuy; Sakasegawa, Yuji; Doh-Ura, Katsumi; Go, Mei-Lin; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2917 – 2929;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics