Month: June 2021

70558-11-1, name is 6-Chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine, 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. Recommanded Product: 6-Chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine

Reference Example 82 Production of (6-chloro-2,3-dihydrobenzo[1,4]oxazin-4-yl)-(3,5-dibromo-4-hydroxyphenyl)-methanone 6-Chloro-3,4-dihydro-2H-benzo[1,4]oxazine (170.6 mg) obtained in Step 3 of Reference Example 51 and 3,5-dibromo-4-hydroxybenzoyl chloride (349.3 mg) obtained in Step 1 of Reference Example 4 were dissolved in ethyl acetate (5 mL), and the mixture was heated under reflux overnight. The solvent was evaporated, and the obtained solid was crystallized from methanol to give the title compound (441.0 mg) as crystals.

The synthetic route of 70558-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; US2008/305169; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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. Formula: C6H4ClN3

a) A mixture of 5 g of 5-chlorobenzotriazole, 1.4 g of chloroacetone, 5.1 g of potassium carbonate and 0.5 g of potassium iodide is stirred into 50 mi of acetone at room temperature for 48 h. The mixture is subsequently filtered, the filtrate concentrated by evaporation in a vacuum, and the residue purified by flash chromatography. In this way, two isomeric products, [1- (5-CHLOROBENZOTRIAZOL-1-YI)-PROPAN-2-ONE] and [1-(6-CHLOROBENZOTRIAZOL-1-YL)-] propan-2-one, are isolated in approximately the same quantities, the first of which is then used directly in the next step.

The synthetic route of 5-Chloro-1H-benzo[d][1,2,3]triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/24704; (2004); 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. 6940-78-9, name is 1-Bromo-4-chlorobutane, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Step 1 Synthesis of 1-(4-Chlorobutyl)-1,5,6,7-tetrahydroindol-4-one: To a solution of 1,5,6,7-tetrahydroindol-4-one (10.0 g, 74.0 mmol) in acetone (300 mL) was added powdered sodium hydroxide (3.26 g, 81.4 mmol) and the mixture stirred at ambient temperature for 0.25 h. 1-Bromo-4-chlorobutane (9.38 mL, 81.4 mmol) was then added and the resulting mixture stirred at ambient temperature for 7 h after which time TLC (ethyl acetate:dichloromethane 1:1) showed complete reaction. The reaction was gravity filtered to remove salts, and the filtrate concentrated to dryness under vacuum. The resulting residue was dissolved in dichloromethane (200 mL) and gravity filtered again to remove more salts. The filtrate was then washed with water, dried with sodium sulfate, filtered and the solvent removed under vacuum to yield an oil. Flash chromatography using 6 in. of silica gel in a 5.5 cm column eluding with 1:1 followed by 2:1 ethyl acetate:hexane on half of the residue yielded 9.0 g of an oil which contained ~6.0 g of pure product (72%) and ~3.0 g of acetone aldol condensation product (4-hydroxy-4-methyl-2-pentanone). The oil was taken to the next step without further purification.

The synthetic route of 6940-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fick, David B.; Foreman, Mark M.; Glasky, Alvin J.; Helton, David R.; US2003/114463; (2003); A1;,
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. 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Chloro-1H-benzo[d][1,2,3]triazole

General procedure: in EtOAc/MeOH (4:1) mixture solvent (2 mL), benzotriazoles 1 (0.3 mmol), sodium sulfinates 2 (0.54 mmol), NaBr (0.36 mmol) and mCPBA (0.39 mmol) were added successively. The suspension mixture was vigorously stirred at room temperature for 4 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL), basified with sat. aq. Na2CO3(8 mL) and H2O (5 mL). The mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (3:1 (v/v) petroleum ether/ethyl acetate) to furnish sulfonylbenzotriazoles 3.

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 94-97-3.

Reference:
Article; Wu, Sixue; Zhang, Yikun; Yan, Jie; Synthetic Communications; vol. 46; 17; (2016); p. 1432 – 1437;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
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. 501-29-1, name is 1-Chloro-2-fluoro-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H6ClFO

To 1- chloro-2-fluoro-4-methoxybenzene (5.00 g, 31.2 mmol) in cone. H2SO4 (30 mL) at -10 C to 0 C, potassium nitrate (3.47 g, 34.4 mmol) was added portionwise to the reaction mixture. The reaction was stirred at 0 C for 2 h. The reaction was quenched with iced water and filtered. The obtained solids were recrystallized with hexanes to give Intermediate 15A (4.8 g, 75%).

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 501-29-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; THIBEAULT, Carl; CLARK, Charles, G.; DELUCCA, Indawati; HU, Carol, Hui; JEON, Yoon; LAM, Patrick, Y., S.; QIAO, Jennifer, X.; YANG, Wu; WANG, Yufeng; WANG, Tammy, C.; WO2014/22349; (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. 95-81-8, name is 2-Chloro-5-methylaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Example 1 Benzoyl chloride (21.9 g) was added dropwise to a stirred mixture of ammonium thiocyanate (13.2 g) in acetone (95 ml) and the mixture stirred for a further 20 minutes at room temperature. A solution of 6-chloro-m-toluidine (22.1 g) in acetone (30 ml) was added dropwise with stirring, the mixture stirred for a further 30 minutes at room temperature and then heated under reflux for 5 minutes. The mixture was added to water, the solid collected, dissolved in aqueous sodium hydroxide (10%; 95 ml) acidified to pH 5 with hydrochloric acid and rebasified to pH 9 with aqueous ammonia. The solid was filtered and recrystallized from toluene to give 1-(6-chloro-m-tolyl)thiourea, m.p. 152-4.

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; SCHERING AGROCHEMICALS LIMITED; EP337616; (1989); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Product Details of 72235-58-6

A mixture of Example 235G (40.0 mg, 0.112 mmol), HATU (1- [bis(dimethylamino)methylene]-lH-l ,2,3-triazolo[4,5-]pyridinium 3-oxid (1666) hexafluorophosphate) (51.0 mg, 0.134 mmol), (4-chloro-3-fluorophenyl)methanamine (0.015 mL, 0.123 mmol), and triethylamine (0.031 mL, 0.224 mmol) in N,N-dimethylformamide (DMF) (1.5 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over MgSO/t, filtered, and concentrated. The residue was purified by HPLC performed on a Phenomenex Luna C18 column (250 x 30 mm, 10 mupiiota particle size) using a gradient of 20% to 100% acetonitrile:0.1 % aqueous trifluoroacetic acid over 26 minutes at a flow rate of 50 mL/minute to provide the title compound (49.6 mg, yield 89%). JH NMR (501 MHz, DMSO- ) delta ppm 8.29 (t, J = 6.3 Hz, 1H), 7.75 (s, 1H), 7.50 (dt, J = 15.1 , 8.5 Hz, 2H), 7.20 (dd, J = 10.4, 2.0 Hz, 1H), 7.11 – 6.99 (m, 2H), 6.82 (ddd, J = 9.0, 2.9, 1.1 Hz, 1H), 4.48 (s, 2H), 4.23 (d, J = 6.3 Hz, 2H), 4.03 (s, 2H), 2.13 – 1.95 (m, 4H), 1.95 – 1.77 (m, 4H); MS (ESI+) m/z 449.3 (M+H)+.

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-Chloro-3-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 72235-58-6,Some common heterocyclic compound, 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, molecular formula is C7H7ClFN, 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.

Step 3: Intermediate 201 OB (50 mg, 0.16 mmol) is dissolved in DMF (2.0 ml_), then diisopropylethylamine (1 10 muIota_, 0.63 mmol, 4.0 eq) and 4-chloro-3-fluorobenzylamine ( Oakwood) (30 mg, 0.19 mmol, 1 .2 eq) are added followed by HATU (78 mg, 0.21 mmol, 1 .2 eq) and the reaction mixture is stirred at RT. Following completion of the reaction, the solution is filtered and purified by preparative HPLC to provide compound 2010 (tR: 1 .71 , (M+H)+: 459.2/461 .2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Chloro-3-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2613-34-5, 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. 2613-34-5, name is 3-Chloro-2,4-difluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2- yl)sulfamoyl)-1H-pyrrole-2-carboxylic acid (450 mg, 1.43 mmol) and 3-chloro-4,5- difluoroaniline hydrochloride (0.57 g, 2.86 mmol) (synthesis described in synthesis for compound 57) and HATU (0.73 g, 1.91 mmol) were dissolved in DMF (2 mL) containingdiisopropylethylamine (0.82 mL, 4.77 mmol). The reaction mixture was stirred at 40C for 66 hours. The reaction mixture was directly loaded on column. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combined and evaporated to keep 50 mL of solvent. The precipitates were filtered and washed with petroleum ether and dried in vacuum oven at 50C overnight to affordcompound 137 (490 mg) as white powder.(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2-yl)sulfamoyl)- 1 H-pyrrole-2-carboxylic acid (168mg, 0.53 mmol) (synthesis described in synthesis for compound 137) 5-amino-2-fluorobenzonitrile (0.15 g, 1.07 mmol) and HATU (0.24 g, 0.64 mmol) were dissolved in DMF (1 mL) containing diisopropylethylamine (0.23 mL, 1.34 mmol). The reaction mixture was stirred at 50C for 1 hour. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combinedand evaporated to keep 50 mL of the solvent. The white solids were filtered and dried invacuum oven to afford compound 140 (180 mg) as white powder.Compound 143 (147 mg) as white powder was synthesized similarly as described for compound140 using 3-chloro-2,4-difluoroaniline (0.17 g, 1.07 mmol) instead of 5-amino-2-fluorobenzonitrile. The reaction mixture was stirred at 60C for 2 hours more. Method B; Rt:1.07 mi mlz: 458 (M-H) Exact mass: 459.04. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.09 (d,J7.0 Hz, 3 H), 2.44 (s, 3 H), 3.82 (s, 3 H), 3.76 – 3.91 (m, 1 H), 7.34 (td, J=9.0, 2.0 Hz, 1 H),7.35 (s, 1 H), 7.52 (td, J8.7, 5.8 Hz, 1 H), 8.20 (br. s., 1 H), 10.05 (s, 1 H).

The synthetic route of 3-Chloro-2,4-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics