Month: June 2021

Reference 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) (83 mg, 0.44 mmol) in IPA (5 mL) was added (lR,3S,5R)-2-azabicyclo[3.1.0]hexan-3-ylmethanol TFA salt (325c) (100 mg, 0.44 mmol) and DIPEA (0.23 mL, 1.32 mmol). The resulting mixture was stirred for 3h at 60 C, cooled to RT and concentrated in vacuum. The residue obtained was purified by flash column chromatography [silica gel (12 g), eluting with 0-60% EtOAc/MeOH (9: 1) in hexane from 0-100%] to afford ((lR,3S,5R)-2-(2-chloropyrrolo[l,2-f][l,2,4]triazin-4-yl)-2- azabicyclo[3.1.0]hexan-3-yl)methanol (325d) (75 mg, 64 % yield) as a semi-solid. MR (300 MHz, DMSO-i) delta 7.73 (t, J = 2.0 Hz, 1H), 7.24 – 7.16 (m, 1H), 6.72 – 6.64 (m, 1H), 4.96 (t, J = 5.8 Hz, 1H, D20 exchangeable), 4.55 – 4.44 (m, 1H), 3.77 – 3.68 (m, 1H), 3.66 – 3.50 (m, 2H), 2.35 – 2.24 (m, 1H), 1.98 – 1.80 (m, 2H), 1.28 – 1.16 (m, 1H), 0.68 – 0.57 (m, 1H); MS (ES+): 265.2 (M+l); (ES-): 299.2, 301.2 (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;,
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Application of 102-49-8, The chemical industry reduces the impact on the environment during synthesis 102-49-8, name is 3,4-Dichlorobenzylamine, I believe this compound will play a more active role in future production and life.

Example 19.7: Preparation of 2-BenzyIoxy-5-morpholin-4-yl-l-oxo-lH-9-oxa-4,9oe- diaza-fluorene-3-carboxylic acid 3,4-dichloro-benzylamidelambdazetalambdaf’-Dicyclohexylcarbodiimide (110 mg, 0.522 mmol) was added to a stirred solution of the product from Example 19.6 (200 mg, 0.475 mmol) in dichloromethane (100 mL), After 30 min, lambdazetaN-dimethylaminopyridine (6 mg, 0.05 mmol), 3,4- dichlorobenzylamine (92 mg, 0.52 mmol) and 1-hyroxybenzotriazole (70 mg, 0.52 mmol) were added successively. The mixture was stirred at room temperature overnight and aqueous work-up and extraction afforded the crude product was further purified by column chromatography (hexane/ethyl acetate 4:1) as eluent to afford the desired product (120 mg, 44 percent) as a yellow solid.1H NMR (300 MHz, CDCl3) delta 3.37-3.45 (m, 4H), 3.85-3.95 (m, 4H), 4.51 (d, J=5.8 Hz, 2H), 5.43 (s, 2H), 6.84 (d, J=8.3 Hz, IH), 7.06-7.16 (m, 2H), 7.28-7.36 (m, 3H), 7.37-7.49 (m, 4H), 7.55-7.71 (m, 2H).

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, 3,4-Dichlorobenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVEXA LIMITED; WO2008/77188; (2008); A1;,
Chloride – Wikipedia,
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Electric Literature of 6940-78-9, A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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.

7.16 g of 7-hydroxy-2-quinolinone, 51.5 g of 1-bromo 4-chlorobutane, 37.32 g of potassium carbonate and4.18g of ethoxyformylmethylenetriphenylphosphine dissolved in 170mL of acetone, reacted at 45 C for 2.5h,After the reaction, 100 ml of a saturated sodium chloride solution was added, followed by extraction with ethyl acetate.The ethyl acetate extract was washed successively with saturated sodium chloride solution and deionized water.Dry over anhydrous sodium sulfate, concentrate under reduced pressure and dried in vacuo.

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; Wuhan Xing Hua Knowledge Pharmaceutical Technology Co., Ltd.; Lu Shan; Chen Jingrun; Zhang Chuantao; (16 pag.)CN109988162; (2019); A;,
Chloride – Wikipedia,
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Application of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

Preparation 19. 1-Methyl-4- (3-chloro-2- fluorophenylamino) piperidine; Combine 3-chloro-2-fluoroaniline (4. 37 g, 30 mmol), 1-methylpiperidin-4-one (3.39 g, 30 mmol), sodium triacetoxyborohydride (5.26 g, 33 mmol), and acetic acid (5.4 g, 90 mmol) and stir at room temperature overnight. Partition the reaction mixture between dichloromethane and saturated aqueous NaCl containing NH40H, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel columnn (110 g), using a gradient of dichloromethane-2M NH3 in methanol to give 2.34 g of the title compound (32% yield): mass spectrum (ion spray): m/z = 243 (M+1) ; 1H NMR (CDC13) : 6.88 (ddd, lH), 6.63 (ddd, 1H), 6.56 (dd, 1H), 3.85 (br d, 1H), 3.28 (m, 1H), 2.80 (m, 2H), 2.30 (s, 3H), 2.13 (m, 2H), 2.04 (m, 1H), 1.53 (m, 2H). (file: mn4-b6k-284-2)

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/35499; (2005); A1;,
Chloride – Wikipedia,
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Electric Literature of 6579-54-0,Some common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, molecular formula is C6H3Cl3O2S, 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 mixture of corresponding 7 (150mg, 0.4mmol) in anhydrous THF (15mL) and DMF(3mL), corresponding sulfonyl chloride (0.5mmol) was added slowly at 0C and stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate (50mL×3). The combined organic layer was washed by saturated sodium chloride solution (40mL×3) and concentrated. The residue was purified by silica gel chromatography to afford 8a-8i.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dichlorobenzenesulfonyl chloride, its application will become more common.

Reference:
Article; Zhang, Li; Zhang, Beichen; Zhao, Jingyun; Zhi, Yanle; Wang, Lu; Lu, Tao; Chen, Yadong; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 942 – 951;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis Methyl 2,2,2-trichloroacetimidate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
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Electric Literature of 329944-72-1, The chemical industry reduces the impact on the environment during synthesis 329944-72-1, name is 3-Bromo-5-chlorotoluene, I believe this compound will play a more active role in future production and life.

Azobisisobutyronitrile (AIBN, 1.0 g, 6.05 mmol) was added to a stirred solution of 1-bromo-3-chloro-5-methylbenzene (25 g, 121 mmol) in CCl4 (250 mL). The reaction mixture was then cooled to 0 C and N-bromosuccinimide (21.65 gm, 121 mmol) was added and the reaction mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and the solid was removed by filtration. The filtrate was concentrated to give the title compound as brown liquid (25 g), which was taken to the next step without further purification.

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, 3-Bromo-5-chlorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cortendo AB; Blass, B. E.; Abou-Gharbia, M. A.; Childers, W. E.; Iyer, P.; Boruwa, J.; (143 pag.)CN105722823; (2016); A;,
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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H6BrCl

EXAMPLE 10; (5-{2-r5-(S-Chloro-2-methylphenvl)hexahvdropyrrolor3.4-clpyrrol-2piH)-vn-13-thiazol-5-vU- 2H-tetrazol-2-yl)acetic acid; Step 1 tert-Butgamma\ 5-(5-chloro-2-methvlphenvpihexahgammadropyrrolo[3,4-clpyrrole-2(lH)- carboxylate; Into a 50 mL flask equipped a magnetic stir bar and a rubber septum was added tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(lH)-carboxylate oxalate (2 00 g, 6 62 mmol),10 palladium(II) acetate (149 mg, 0 66 mmol), racemic-B INAP (824 mg, 1 32 mmol) and sodium tert-butoxide (1 91 g, 19 9 mmol) The vial was evacuated under vacuum (10 mm Hg) and backfilled with N2 (repeated 3 times) Toluene (14 mL) and 2-bromo-4-chlorotoluene (2 18 g, 10 6 mmol) were added to the flask and the solvent was degassed for 10 mm with a steady flow of nitrogen before being heated to 115 0C for 20 h The reaction mixture was partitioned between15 EtOAc (200 mL) and water (150 mL) The aqueous layer was extracted with EtOAc (5 x 50 mL) and the combined organic layers were washed with brine, dried over Na?Spsi4 and concentrated The resulting pale brown oil was purified by column chromatography on silica gel, elutmg with 0percent EtOAc m hexanes to 40percent EtOAc m hexanes as a gradient The desired product was obtained as a yellow oil

The synthetic route of 27139-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; LACHANCE, Nicolas; LEGER, Serge; OBALLA, Renata, M.; POWELL, David; TRANMER, Geoffrey, K.; MARTINS, Evelyn; GAREAU, Yves; WO2010/108268; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 14752-66-0, 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 14752-66-0 as follows.

General procedure: In nitrogen atmosphere, sodium benzenesulfinate (1a, 0.3 mmol, 1.5 equiv, 49 mg), Ag2CO3 (0.3 mmol, 1.5 equiv, 83 mg) and Pd(PtBu3)2 (0.006 mmol, 3 mol %, 3 mg) were weighed in a 10 mL reaction tube. N,N-Dimethylacetamide (2 mL), hexabutyldistannane (2a, 0.2 mmol, 1 equiv, 116 mg, 101 muL) were then added in succession. The resulting reaction solution was stirred for 1 h at 140 C. The reaction system was filtered by siliga gel to remove the insoluble precipitate. The solution was concentrated under reduced pressure to evaporate the solvent, and then the crude product was purified by silica gel column chromatography (petroleum ether) to obtain tributyl(phenyl)stannane (3a) in 97% isolated yield (71 mg) as colorless liquid.

According to the analysis of related databases, 14752-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lian, Chang; Yue, Guanglu; Zhang, Haonan; Wei, Liyan; Liu, Danyang; Liu, Sichen; Fang, Huayi; Qiu, Di; Tetrahedron Letters; vol. 59; 45; (2018); p. 4019 – 4023;,
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, HPLC of Formula: C6H3ClF2O2S

To a suspension of 5-bromo-2-methoxypyridin-3-amine (6.3 g, 31 mmol) in pyridine (25 mL) was added 2,4-difluorobenzene-1-sulfonyl chloride (16.47 g, 77.5 mmol). The reactionwas stirred at 23C for 24 h. The solvent volume was then reduced to 50% under reduced pressure. The resulted solid was collected by filtration, and was washed with i-PrOH (5 mL x 2)followed by Et20 (5 mL). A suspension of the above solid and NaOH (2.48 g, 62 mmol) inMeOH (25 mL) was stirred at 23C for 1 h and then concentrated in vacuo. The residue wasdiluted with DCM (20 mL) and 2M HCl (20 mL), adjusted to pH 7 with 5% aq. NaHC03, andthen extracted with DCM (20 mL x 3). The combined organic phases were washed with brine (20mL), dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound as apale yellow solid (8.2 g, 69.9%). The title compound was characterized by LC-MS and 1HNMR as shown below:LC-MS (ESI, pos. ion) m/z: 379 [M+Ht;1HNMR (400 MHz, CDCh) 8 (ppm): 3.89 (s, 3H), 6.90-7.01 (m, 2H), 7.80-7.83 (d, J= 2.24 Hz,1H), 7.86-7.93(m, 2H).

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; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Zhuo; WANG, Tingjin; WU, Zuping; WEN, Qiuling; WO2014/22128; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics