Month: November 2020

A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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. 6346-09-4.

Synthesis of phthalimide lb.; To a stirred solution of 4-aminobutyraldehyde diethyl acetal la (89.3 mmol) in CH3CN (100 mL) was added N-carbethoxyphthalimide (93.8 mmol). Once the reaction was complete, the acetonitrile was removed under reduced pressure and the aqueous phase extracted with EtOAc (x3). The organic phase were combined, then washed with water (x4), saturated brine (x3), then dried (Na2S04), filtered, and evaporated under reduced pressure to give the title compound lb, which crystallized on standing.

The synthetic route of 4,4-Diethoxybutan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; WO2005/70930; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., 111-95-5

(1)N’5′-[2-Chloro-4-(trifluoromethyl)phenyl]-N’5′-ethyl-2-(4-methoxybenzyl)-N’7′,N’7-bis(2-methoxyethyl)-2H-pyrazolo[4,3-d]pyrimidine-5,7-amine A mixture of 7-chloro-N-[2-chloro-4-(trifluoromethyl)phenyl]-N-ethyl-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine-5-amine(a compound obtained in Reference Example 16) (75 mg), N,N-diisopropylethylamine(18.2 mg) and bis(2-methoxyethyl)amine(93.7 mg) in N-methylpyrrolidone(1.1 mL) was stirred at outside temperature of 110C under argon gas atmosphere overnight. After being cooled to room temperature, water and chloroform were added to the reaction mixture, the separated organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was evaporated under reduced pressure. The resulted residue was purified by using a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:2) to give the titled compound(84.3 mg) quantitatively as a pale yellow liquid. MS(APCI)m/z:593/595[M+H]+.

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; Mitsubishi Tanabe Pharma Corporation; EP1903045; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

52189-63-6, Adding some certain compound to certain chemical reactions, such as: 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, 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 52189-63-6.

Boron tribromide (1 M in dichloromethane, 9mL, 89.985mmol) was added drop wise to an ice- cooled solution of 3,5-dimethoxy fluorobenzene (3ml, 22,496mmol) in dichloromethane (2OmL) and the mixture was stirred at O0C to room temperature for 4 hours. The solution was cooled to O0C, further boron tribromide (4ml, 44.992mmol) was added and stirring continued, warming to room temperature for an additional 18 hours. The reaction was quenched with 0.88 ammonia solution and stirred at room temperature for 90 minutes. The organic layer was separated and extracted with 2N sodium hydroxide (30ml), which was then acidified to pH1 by drop wise addition of concentrated hydrochloric acid. The aqueous layer was then re- extracted with dichloromethane (3x15mL), the combined organic solution was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid in 54% yield, 1.72g. 1HNMR(400MHz, CD3OD) delta: 3.72(s, 3H), 6.07-6.15(m, 3H)

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 52189-63-6.

Reference:
Patent; PFIZER LIMITED; WO2007/34325; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

929-75-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 929-75-9 name is 1,11-Diamino-3,6,9-trioxaundecane, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

N-i^e-Dichlorotl^^Jtriazin^-y -HO-dimethyl-hydroxylamine (XXX) (1.63 g, 7.8 mmol) in EtOH (100 mL) was added to 2,2′-(2,2*-oxybis(ethane- 2,l-diyl)bis(oxy))diethanamine {Org. Biomol. Che . 2005, 3:2255-61) (1.5 g, 7.8 mmol) and DIPEA (2.01 g, 15.6 mmol). The reaction was heated at 100 C for 3 h, after which time the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (200 mL), washed with water (2 x 100 mL) and then with a brine solution (100 mL) and lastly dried over Na2S0 . The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (DCM MeOH=50/l to 20/1) to yield N-(5,8,l l-trioxa-2, 14,16,18,19- pentaazabicyclo[l 3.3.1 ]nonadeca-l(l 8), 15( 1 ), 16( 17)-trien-l 7-yl)-N,0- dimethylhydroxylamine (CXVII) (700 mg) as a colourless oil (yield 27%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,11-Diamino-3,6,9-trioxaundecane, and friends who are interested can also refer to it.

Reference:
Patent; GALLEON PHARMACEUTICALS, INC.; DAX, Scott, L.; WOODWARD, Richard; PENG, Sean; WO2012/74999; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 103-50-4, name is Benzyl ether, belongs to ethers-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 103-50-4, 103-50-4

General procedure: To a stirred solution of ether (1.0 mmol) in AcOH (6 mL), was added 30 mol % of BF3¡¤Et2O followed by the addition of cyanamide (1.0 mmol). The reaction mixture was refluxed at an elevated temperature (40-50 C) till the completion of the reaction as monitored by TLC. Upon complete consumption of the cyanamide, the reaction medium was diluted with EtOAc (15 mL). The organic layer was washed with water followed by 5% NaHCO3 (2 ¡Á 5 mL), water (2 ¡Á 5 mL), and brine (5 mL). The organic layer was then dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo to afford the crude which was then purified through silica gel column chromatography (30-40% EtOAc/hexane).

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, Benzyl ether, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Panduranga, Veladi; Basavaprabhu; Sureshbabu, Vommina V.; Tetrahedron Letters; vol. 54; 8; (2013); p. 975 – 979;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The chemical industry reduces the impact on the environment during synthesis 6346-09-4, name is 4,4-Diethoxybutan-1-amine, I believe this compound will play a more active role in future production and life. 6346-09-4

To a solution of commercially available 4-aminobutyaldehyde diethyl acetal (21)[1] (5.00 g, 31.0 mmol) in THF (75 mL) was added TEA (6.50 mL, 4.70 g, 46.5 mmol) at 0-5 C (ice-bath temperature). The mixture was allowed to stir for 5 min, and treated with a solution of Boc2O (6.76 g, 31.0 mmol) in THF (30 mL) drop-wise. The reaction mixture was stirred at 0-5 C for 30 min and allowed to warm to RT.and stir for 3 h. The mixture was transferred to a separatory funnel and partitioned with H2O (100 mL) and EtOAc (200 mL). The organic layer was separated, dried (anhydrous Na2SO4), filtered and concentrated to afford 7.71 g (95% yield) of compound 22 as a viscous slightly yellow oil: 1H NMR (400 MHz,CDCl3) delta 4.63 (bs, 1H), 4.46 (t, J = 5.39 Hz, 1H), 3.55 (ABq of q, J = 9.32, 7.14 Hz, Dn = 62.10 Hz, 4H), 3.12 (q, J = 6.40 Hz, 2H), 1.65 – 1.60 (m, 2H), 1.57 – 1.50 (m, 2H), 1.42 (s, 9H), 1.18 (t, J = 6.90 Hz, 3H). 13C NMR (100 MHz, DMSO-d6) delta 156.10, 102.47, 77.83, 60.99, (BocNHCH2- obscured by DMSO solvent peak ), 31.18, 28.78, 25.36, 15.83. HRMS ESI-TOF (m/z) = 284.1814 (284.1832 calculated for C13H27NO4Na) [M+Na].

The chemical industry reduces the impact on the environment during synthesis 6346-09-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Omran, Anahid; Eslamimehr, Shakiba; Crider, A. Michael; Neumann, William L.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1897 – 1902;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

103-50-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 103-50-4 name is Benzyl ether, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a sealed tube containing the respective azobenzene 1 (0.25 mmol), dibenzyl ether 2 (0.75 mmol), Pd(OAc)2 (0.025 mmol), and DCE/AcOH (1:1, v/v, 1 mL in all) was added TBHP (1.5 mmol). After stirring vigorously at 60 C for 12 h, the mixture was evaporated under vacuum. The corresponding product 3 was isolated by silica gel column chromatography with a PE/EtOAc mixture as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl ether, and friends who are interested can also refer to it.

Reference:
Article; Hong, Gang; Aruma, Alfred Njasotapher; Zhu, Xiaoyan; Wu, Shengying; Wang, Limin; Synthesis; vol. 48; 8; (2016); p. 1147 – 1158;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, belongs to ethers-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. 35896-58-3

2,3,4,5-Tetramethoxytoluene 3 (2.1 g, 10 mmol) and NaBr (1.1 g, 10 mmol) were dissolved in AcOH (5 mL), a solution of 30% H2O2 (1.2 mL, 10 mmol) was added dropwise over 5 min at room temperature. The mixture was stirred and heated at 40 C for 1 h and quenched with H2O( 5 mL) and extracted with diethyl ether (3 ¡Á 30 mL). The combined organic phases were washed with saturated NaHCO3(3 ¡Á 10 mL) until pH 7, then dried over anhydrous Na2SO4,and evaporated under reduced pressure to give yellow oil 4 (2.9 g) in quantatitive yield. 1H NMR (400 MHz, CDCl3) delta 3.92 (s, 3H, OCH3), 3.91(s, 3H, OCH3), 3.85 (s, 3H, OCH3), 3.79 (s, 3H, OCH3),2.30 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)delta 148.3, 147.2, 146.3,145.5, 127.3, 114.3, 61.4 (OCH3), 61.1 (OCH3), 60.9(OCH3), 60.8 (OCH3), 15.9 (CH3). GC-MS (EI): m/z = 290.

Statistics shows that 35896-58-3 is playing an increasingly important role. we look forward to future research findings about 1,2,3,4-Tetramethoxy-5-methylbenzene.

Reference:
Article; Qiu, Yong-Fu; Lu, Bin; Yan, Yi-Yu; Luo, Wan-Yue; Wang, Jin; Hu, Xiao; Chemical Papers; vol. 73; 11; (2019); p. 2745 – 2748;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

321-28-8, Adding some certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-methoxybenzene, 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 321-28-8.

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone. acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 ML), maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C. before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol).. The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L).. The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 ML).. The combined organic layers were washed with water (2*150 ML), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 ML. Hexanes were added and a white solid formed which was isolated by filtration and air dried.. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92-94 C.

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 321-28-8.

Reference:
Patent; G. D. Searle & Co.; US6342510; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5111-65-9,Some common heterocyclic compound, 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, molecular formula is C11H9BrO, 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 21.2: 6-methoxy-naphthalen-2-ylamine A solution of 2-bromo-6-methoxy-naphthalene (237 mg, 1 mmol), Pd (dba)2 mg, 0.05 mmol), tri-t-buthylphosphonium tetrafluoroborate (14 mg, 0.05 mmol), and lithium bis (trimethylsilyl)amide (1 M in hexane, 1.1 mL, 1.1 mmol) is stirred in toluene (2.5 mL) under argon for 6 h. The reaction mixture is taken in diethyl ether (20 mL), and quenched with 1 M HCI. The organic phase is extracted with water, the combined aqueous phases are treated with 1 M sodium hydroxide and extracted with DCM. The combined organic phases are dried over magnesium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (ethyl acetate) to afford 6-methoxy- naphthalen-2-ylamine (110 mg, 64 %), HPLC tR : 3.07, (M+H) + = 173.9.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem