Tag: M.W=200-300

These common heterocyclic compound, 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, 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. Computed Properties of C8H11Cl2NO

Preparation of Compound IV:3-Chloro-4-methoxybenzylamine hydrochloride III (25.00 g, 0.12 mol)Suspended in 75mL acetonitrile,Add sodium bicarbonate (23.21 g, 0.27 mol),Compound II (22.02 g, 0.11 mol) was added,Stir at 40 degrees for 2.5 hours.The reaction solution was suction filtered,The filter cake was washed once with 10 mL of acetonitrile.Wash once with 10 mL of water.After the filter cake is dried by phosphorus pentoxide,32.01g of white solid compound IV,The yield was 87.37%.

The synthetic route of 3-Chloro-4-methoxybenzylamine Hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tierxi (Nanjing) Pharmaceutical Research And Development Co., Ltd.; Wu Wenchao; Song Dandan; Zhang Chi; Cui Xilin; (10 pag.)CN110117274; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 309721-44-6, name is 2-Bromo-1-chloro-3-fluorobenzene, 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 309721-44-6, COA of Formula: C6H3BrClF

A mixture of 146.1 g (1.36 mol) of p-toluidine, 12.6 g (0.02 mol) of (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 261.9 g (2.73 mol) of sodium t-butoxide, 314.1 g (1.50 mol) of 2-bromo-3-fluoro-chlorobenzene and 6.3 g (0.0069 mol) of tris(dibenzylideneacetone)dipalladium(0) in 3000 ml of toluene is heated to 110 over 30 minutes and stirred an additional 4 hours at this temperature. The mixture is cooled to room temperature and a solution of 680 ml 37% hydrochloric acid and 680 ml of water is added over 15 minutes. The mixture is stirred for 20 minutes and filtered through a pad of Celite. The layers are separated and the organic phase is washed twice with 680 ml of water and once with a solution of 225 g of sodium chloride in 680 ml of water. The solvents are evaporated under reduced pressure to give N-(2′-chloro-6′-fluorophenyl)-4-methylaniline as an oil, b.p. 129-131/0.5 mm Hg.

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, 2-Bromo-1-chloro-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novartis AG; US6291523; (2001); B1;,
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Reference of 73006-78-7,Some common heterocyclic compound, 73006-78-7, name is 5-Chloro-[1,1′-biphenyl]-2-amine, molecular formula is C12H10ClN, 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: General Method A: Synthesis of an isocyanate from an aniline To a solution of the aniline (5.21 mmol, 1.00 equivalent) in toluene (19.0 ml), triphosgene (0.35 equivalents) is added slowly and the reaction mixture is heated to reflux for 1 h. The reaction mixture is concentrated to dryness and the product is either purified by bulb-to-bulb distillation or used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-[1,1′-biphenyl]-2-amine, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RICHTER, Hans; WO2014/146994; (2014); A1;,
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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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., Product Details of 1996-30-1

2-Fluoro-5-chlorobromobenzene 18a (11.0 g, 52.8 mmol), ethynyltrimethylsilane (7.7 g, 79 mmol) and triethylamine (60 mL) were mixed together, and then cuprous iodide (100 mg, 0.53 mmol) and ditriphenylphosphine palladium chloride (1.86 g, 2.65 mmol) were added, the reaction mixture was heated to 80 C. under a nitrogen atmosphere and stirring was continued for 4 hours, after the reaction was completed, the solvent was removed from the solution under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=100/1), so as to obtain the title product ((2-fluoro-5-chlorophenyl)ethynyl)trimethylsilane 18b (11.0 g, yellow oily substance), and the yield was 90%. 1H NMR (400 MHz, CDCl3) delta 7.45 (dd, J=6.0, 2.7 Hz, 1H), 7.28-7.22 (m, 1H), 7.02 (t, J=8.8 Hz, 1H), 0.29 (s, 9H).

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; BEIJING INNOCARE PHARMA TECH CO., LTD.; Chen, Xiangyang; Gao, Yingxiang; Kong, Norman Xianglong; (59 pag.)US2019/210997; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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 60811-21-4, Product Details of 60811-21-4

To an oven dried 8 mL vial with teflon cap purged with N2 was added Zinc dust (298 mg, 4.56 mmol), DMF(1.5 mL), and iodine (57.8 mg, 0.228 mmol). To this mixture was added (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (500 mg, 1.519 mmol), immediately followed by iodine (57.8 mg, 0.228 mmol).Pd2(dba)3 (69.6 mg, 0.076 mmol), 2-dicyclohexylphosphino-2?6-dimethoxybiphenyl (62.4 mg, 0.152 mmol)and 4-bromo-2-chloro-1-fluorobenzene (477 mg, 2.279 mmol) were then added and the reaction mixture wasallowed to stir at 50 C. for 3 hours. The crude mixture was diluted in 30 mL of EtOAc and DMF wasremoved with 4 aqueous washes. The organic phase was dried over anhydrous sodium sulfate. The solutionwas filtered and concentrated, and the crude product was purified by silica gel chromatography using 100%hexanes to 30% EtOAc/Hexanes. The desired product was obtained as a pale yellow oil, (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-fluorophenyl)propanoate (0.174 g, 35%). 1H NMR (400 MHz,chloroform-d) delta 7.27 (s, 1H), 7.17 (dd, J=6.9, 1.4 Hz, 1H), 7.11-6.93 (m, 1H), 5.03 (d, J=6.8 Hz, 1H), 4.55(d, J=6.4 Hz, 1H), 3.73 (s, 3H), 3.19-3.04 (m, 1H), 2.98 (dd, J=13.9, 5.9 Hz, 1H), 1.49-1.37 (m, 10H).

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, 4-Bromo-2-chloro-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; Miller, Michael Matthew; Mapelli, Claudio; Allen, Martin Patrick; Bowsher, Michael S.; Boy, Kenneth M.; Gillis, Eric P.; Langley, David R.; Mull, Eric; Poirier, Maude A.; Sanghvi, Nishith; Sun, Li-Qiang; Tenney, Daniel J.; Yeung, Kap-Sun; Zhu, Juliang; Reid, Patrick C.; Scola, Paul Michael; (892 pag.)US9308236; (2016); B2;,
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Electric Literature of 933190-51-3, The chemical industry reduces the impact on the environment during synthesis 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life.

Preparation of 6-chloro-N-cyclopropylimidazo[1,2-b]pyridazin-8-amine To a solution of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (1.00 g, 3.21 mmol, 1.0 equiv) and p-TSA (611 mg, 3.21 mmol, 1.0 equiv) in DMSO (10.0 mL) was added cyclopropylamine (1.13 mL, 16.1 mmol, 5.0 equiv) and heated to 100 C. for 24 h. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 536 mg of the white solid, 80%.

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, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Califia Bio, Inc.; GOODFELLOW, VAL S.; NGUYEN, THONG X.; RAVULA, SATHEESH B.; GELBARD, HARRIS A.; US2014/256733; (2014); 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 63624-28-2 as follows. Application In Synthesis of 2,4-Dimethoxybenzene-1-sulfonyl chloride

620 mg of the compound obtained in step 15-1 (diastereoisomer mixture) was added under ice cooling and a nitrogen atmosphere to a 10 mL N,N-dimethylformamide solution of 67 mg of sodium hydride, and the reaction mixture was stirred for 40 minutes. After this, a 2 mL N,N-dimethylformamide solution of 400 mg of 2,4-dimethoxybenzenesulfonyl chloride was added dropwise. The reaction mixture was stirred for 30 minutes at the same temperature, after which 5 mL of ethyl acetate and 10 mL of a 5% potassium carbonate aqueous solution were added, and the reaction mixture was stirred at room temperature overnight. The precipitated solids were filtered off and separated and purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone = 99/1; v/v) to obtain two kinds of diastereoisomer of the titled compound in amounts of 184 mg (isomer A: colorless, amorphous) and 256 mg (isomer B: colorless, amorphous). Isomer A: [alpha]D25 = -225 (c = 0.187, chloroform) MS (ESI pos.) m/z : 612([M+H]+), (ESI pos.) m/z : 634([M+Na]+) 1 H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.53 – 1.62 (m, 1 H), 1.85-1.98 (m, 1 H), 2.18 – 2.32 (m, 7 H), 2.75 (s, 3 H), 3.10-3.25 (m, 1 H), 3.55-3.86 (m, 9 H), 4.89-5.01 (br, 1 H), 5.21 – 5.39 (m, 1 H), 6.40 (d, J=1.8 Hz, 1 H), 6.58 (dd, J=9.0, 2.3 Hz, 1 H), 6.76 (d, J=7.9 Hz, 1 H), 6.85 – 6.97 (m, 2 H), 7.07 (dd, J=8.5, 1.2 Hz, 1 H), 7.17 – 7.24 (m, 1 H), 7.74 – 7.84 (m, 2 H), 8.15 (d, J=8.8 Hz, 1 H) Isomer B: [alpha]D25 =+142 (c = 0.240, chloroform) MS (ESI pos.) m/z : 612([M+H]+), (ESI pos.) m/z : 634([M+Na]+) 1 H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.81 – 1.96 (m, 1 H), 2.11 – 2.23 (m, 4 H), 2.46 (s, 3 H), 2.62 (s, 3 H), 3.24 (s, 3 H), 3.36 – 3.49 (m, 1 H), 3.73 – 3.87 (m, 7 H), 4.06-4.11 (m, 1 H), 5.00 – 5.15 (m, 1 H), 6.47 (d, J=2.4 Hz, 1 H), 6.60 (dd, J=9.0, 2.3 Hz, 1 H), 6.66 – 6.73 (m, 2 H), 7.03 – 7.10 (m, 2 H), 7.18 – 7.24 (m, 1 H), 7.81 (d, J=8.2 Hz, 1 H), 8.15-8.25 (m, 2 H)

According to the analysis of related databases, 63624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1659121; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 61881-19-4, A common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.

Compound II – 1 (200 mg, 0 . 187 mmol), N – benzene three fluorine second grades acyl chloride (116 mg, 0 . 56 mmol, 3 eq) dissolved in 5 ml acetone, batches adding potassium carbonate (77 mg, 0 . 56 mmol, 3 eq), stirring at room temperature 1 hour (TLC detection consumption end), filtering, the filtrate turns on lathe does, column to obtain white solid (229 mg, yield 99%)

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 Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Lin Feng; Lu Rui; Xu Qiulong; Chen Jianli; Han Jine; (33 pag.)CN104231009; (2017); B;,
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1205-71-6, name is 4-Chloro-N-phenylaniline, 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. COA of Formula: C12H10ClN

Example 1.106: Preparation of Sodium 2-(((lr,4r)-4-(((4- Chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetate.; Method 1.; Step A: Preparation of ((lr,4r)-4-(hydroxymethyl)cyciohexyI)methyl 4- chlorophenyl(phenyl)carbamate.; 4-Chloro-N-phenylaniline (15.0 g, 73.6 mmol), tribasic potassium phosphate, (fine powder, 4.69 g, 22.1 mmol), N^V-carbonyldiimidazole (13.14 g, 81 mmol) and acetonitrile (75 mL) were charged to a 500-mL, jacketed, four-necked cylindrical reaction flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 65 0C under nitrogen and monitored by HPLC. After about 2.5 h HPLC showed > 98% conversion to the intermediate N-(4-chlorophenyl)-N-phenyl-lH-imidazole-l-carboxamide. After about 5.5 h a solution of (lr,4r)-cyclohexane-l,4-diyldimethanol (37.2 g, 258 mmol) in acetonitrile (150 mL) at 65 0C was added to the reaction mixture over 20 min. The resulting mixture was heated at 65 0C overnight. etaPLC showed about 98% conversion to the required product. The mixture was filtered, and the cake was rinsed with acetonitrile (2 x 25 mL). The filtrate was concentrated under reduced pressure (40 0C, 32 torr) 124.125 g of distillate was collected. The residue was diluted with water (50 mL) and this mixture was concentrated under reduced pressure (400C, 32 torr) and 35.184 g of distillate was collected. The residue was diluted with water (50 mL) and the resulting mixture was allowed to stir overnight to give a white paste. The mixture was filtered, and the cake was rinsed with 25% acetonitrile/water (2 x 75 mL). The solid was dried in a vacuum oven to leave a white solid (22.271 g); 94.8% purity by etaPLC peak area. LCMS m/z = 374.3 [M+eta]+; 1H nuMR (400 MHz, DMSO-^6) delta ppm 0.77 – 0.93 (m, 4 H) 1.23 (dd, J = 6.22, 3.51 Hz, 1 H) 1.47 (dd, J = 6.32, 2.91 Hz, 1 H) 1.56 – 1.76 (m, 4 H) 3.20 (t, J= 5.78 Hz, 2 H) 3.92 (d, J = 6.13 Hz, 2 H) 4.33 (t, J = 5.31 Hz, 1 H) 7.28 – 7.35 (m, 5 H) 7.38 – 7.47 (m, 4 H).

The synthetic route of 1205-71-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
Chloride – Wikipedia,
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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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, A new synthetic method of this compound is introduced below., SDS of cas: 6579-54-0

The methyl 4-(morpholine-2-carboxamido)adamantine-1-carboxylate compound (174.0 mg, 0.54 mmol) was dissolved in CH2Cl2 (4 ml), and 2,6-dichlorobenzenesulfonyl chloride (132.6 mg, 0.54 mmol) and triethylamine (120.2 mg, 1.19 mmol) were added thereto, followed by stirring at room temperature for 3 hours. H2O was added to the reaction solution, which was then extracted three times with CH2Cl2. The extract was dried with MgSO4, filtered and distilled under reduced pressure to remove the solvent. The residue was separated by column chromatography, thereby obtaining a methyl 4-(4-((2,6-dichlorophenyl)sulfonyl)morpholine-2-carboxamido)adamantane-1-carboxylate compound (243.9 mg, 0.46 mmol, 85 %).[2013] 1H NMR (400 MHz, CDCl3) delta7.53-7.48 (m, 2H), 7.39-7.33 (m, 1H), 6.92 (br, -CONH), 4.15-4.00 (m, 4H), 3.85-3.63 (m, 5H), 3.13-3.06 (m, 1H), 2.90-2.84 (m, 1H), 2.07-1.54 (m, 13H).

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; HYUNDAI PHARM CO., LTD.; LEE, In Hee; PARK, Chang Min; KIM, Se Hoan; CHAE, Hee Il; PYEON, Doo Hyeok; SHIN, Myoung Hyeon; HWANG, Jeong Un; MOON, Soon Young; HA, Tae Young; KIM, So Youn; CHOI, Hyuk Joon; YOO, Myoung Hyun; LEE, Jong Chan; KIM, Young Seok; RHEE, Jae Keol; WO2012/128582; (2012); A2;,
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