Month: July 2021

38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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. HPLC of Formula: C9H13NO

A mixture of e-1 (0.0037 mol) and e-2 (0.0151 mol) was stirred at 60C for 2 hours, then purified by column chromatography over silica gel (eluent: CH2CyCH3OH (98/2); 15mum). The pure fractions were collected and the solvent was evaporated. Yield: 1 g of intermediate e-3 (100%).

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136561; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 3616-56-6, A common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, 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.

EXAMPLE 43 N,N-Diethyl-5-[[2-(dimethylamino)ethyl]amino]-2H-[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine A mixture of 5.0 g (0.015 mol) of 5-amino-N,N-diethyl-2H[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine, 2.4 g (0.015 mol) of 2,2-diethoxy-N,N-dimethyl ethanamine, and 0.001 g of p-toluenesulfonic acid in 100 ml of 2-propanol was heated under reflux for four hours, allowed to cool to room temperature, and treated portionwise with 1.0 g (0.026 mol) of NaBH4 over a two hour period. The mixture was stirred at room temperature for 16 hours and poured into 1 l of H2 O. The precipitate that formed was collected, washed with H2 O, dried, and recrystallized to give the product. An example of another 5-(monoalkylated or acylated)-2-(substituted)benzothiopyrano[4,3,2-cd]-indazole, prepared in the manner of Examples 5-11, is as follows: N-[2-[2-(diethylamino)ethyl]-2H[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]-1,3-propanediamine, hydrochloride salt, mp 222° C. dec.

The synthetic route of 3616-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4604390; (1986); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, 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: C7H7F3N2O

2-Hydroxymethyl- and 2-ethyl-5-trifluoromethoxybenzimidazole. The procedure of Philips, M. A. was used. A mixture of 2-amino-4-trifluoromethoxyaniline (0.7 g, 0.0036 Mol) and corresponding carboxylic acid (0.00546 Mol) in HCl (3.5 ml, 4N) was refluxed for 6 h. Water (5 mL), and 0.5 g of charcoal were added, and the mixture was refluxed 10-15 min. After cooling, the mixture was filtered and resulted clear filtrate was washed with ether (2×10 mL). The water layer was neutralized with excess of diluted NH4OH, the precipitate was filtered, washed with water, and dried.2-Hydroxymethyl-5-trifluoromethoxybenzimidazole. Glycolic acid was used, R(HO)CH2. Yield 0.65 g (75 wt. %). M.p. 192-194 C. 1H NMR (DMSO-d6): 4.68 (d, 5.5 Hz, 2H), 5.67 (t, 5.5 Hz, 2H), 7.05 (d, J=8.0 Hz, 1H), 7.38 (s, 1H), 7.49 (br s, 1H), 12.48 (br s, 1H). 13C NMR (DMSO-d6): 57.62, 104.44, 110.79, 111.98, 114.70, 118.20, 120.08 (q, J=254.8 Hz), 143.21, 157.22. 19F NMR (DMSO-d6): -57.76. [M+1]+ 233.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 658-89-9, its application will become more common.

Reference:
Patent; The United States of America as represented by the United States Department of Energy; US8242284; (2012); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 36449-75-9, 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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 76 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(2-methoxyphenethyl)imidazolidine-2,4-dione Prepared as in example 52 from 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (example 1) and 2-methoxyphenethyl bromide. Yield: 52%. 1H NMR (DMSO-d6, 400 MHz): delta2.11 (s, 3H), 2.38 (s, 3H), 2.80 (t, J=7.2 Hz, 2H), 3.51 (t, J=7.2 Hz, 2H), 3.75 (s, 3H), 4.03 (s, 2H), 5.17 (s, 2H), 6.85 (t, J=7.2 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 7.16-7.21 (m, 2H), 7.73 (s, 1H), 8.13 (s, 1H). MS M+H calculated 410.2. found 410.1. Melting point: 97-98 C. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.14 muM. Example 52 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,5,5-trimethylimidazolidine-2,4-dione 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-5-methylimidazolidine-2,4-dione (example 41) (50 mg, 0.173 mmol) and 60% NaH (8 mg, 0.190 mmol) were mixed in DMF (1 mL) for 30 minutes. MeI (0.04 mL, 0.190 mmol) was added and the reaction was stirred an additional 4 hours. The reaction was acidified with 1N HCl and diluted with ethyl acetate (2 mL). The organic phase was dried, filtered and solvent was removed under a stream of nitrogen. The crude product was re-suspended in MeOH (1 mL) and purified by reversed phase HPLC (5 to 95% acetonitrile in H2O: 16 minutes gradient). The pure fractions were combined and solvent removed under vacuum to afford 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,5,5-trimethylimidazolidine-2,4-dione as a white solid (25 mg, 50%). 1H NMR (CDCl3, (CDCl3, 400 MHz): delta 1.45 (s, 6H), 2.19 (s, 3H), 2.42 (s, 3H), 2.94 (s, 3H), 5.05 (s, 2H), 7.92 (s, 1H), 8.08 (s, 1H). The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.80 muM.

The chemical industry reduces the impact on the environment during synthesis 1-(2-Bromoethyl)-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SENOMYX, INC.; PATRON, Andrew; TACHDJIAN, Catherine; SERVANT, Guy; DITSCHUN, Tanya; (257 pag.)US2016/376263; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 54314-84-0,Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

26.1.N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamideA mixture of 1 g (3.84 mmol) of 6-chloro-N-cyclopentylpyridine-3-sulfonamide, 1.32 g (9.59 mmol) of K2CO3 and 0.88 mL (4.99 mmol) of [(3-bromopropoxy)methyl]benzene in 8 mL of anhydrous DMF is heated for 12 hours at 40° C.After cooling to room temperature, the medium is taken up in 300 mL of EtOAc, washed successively with water (2*100 mL), saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10percent EtOAc.1.65 g of N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamide are thus obtained in the form of an oil.Yield=99percent.1H NMR, CDCl3, 400 MHz, delta (ppm): 8.85 (s, 1H); 8.1 (d, 1H); 7.5 (d, 1H); 7.4-7.3 (m, 5H); 4.5 (s, 2H); 4.2 (m, 1H); 3.6 (t, 2H); 3.2 (dd, 2H); 2.1 (m, 2H); 1.6-1.3 (m, 8H)

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; US2011/294788; (2011); A1;,
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. 1758-46-9, name is 2-Phenoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Phenoxyethylamine

An oven-dried vial was subsequently charged with 0.1 eq. of a palladium source [Pd], 0.2 eq. (biph)P(betau)2, 1.0 eq. arylhalide B with X = -O-Benzyl, -O-Methyl, -CN or – C(=O)-OCH3 and 1.4 eq. base. The vial was evacuated and purged with argon, and the respective amine HNR1R2 (1.3 eq.) was added. The solvent was added to obtain a concentration of 1.0 M of the arylhalide B. The vial was sealed and heated to either 1000C in case of toluene as the solvent or 110°C in case of DME as the solvent in each case for 22 h. EPO The reaction mixture was transferred into a flask using H2O and MeOH and the total volume was reduced to less than 10 mL Purification was achieved by prep. HPLC. In order to remove any ammonium formate derivative formed during preparative HPLC, the resulting product was taken up in chloroform, extracted twice with saturated aq. NaHCO3, the combined aq. phases were re-extracted with chloroform, and the combined organic phases were dried over MgSO4. If any additional workup was applied, this is indicated in the table 1.

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 1758-46-9.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; WO2006/69807; (2006); A1;,
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. 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromo-1,4-dimethoxybenzene

EXAMPLE 214 [1,2-Dihydro-9-methoxy-2,2,4-trimethyl-5-coumarino3,4-f]quinoline (Compound 314, structure 41 of Scheme XI, where R1 =H, R2 =methoxy) 2,5-Dimethoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =methoxy) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 1-bromo-2,5-dimethoxybenzene (2.00 mL, 13.3 mmol), n-BuLi (2.5M in hexanes; 5.34 mL, 13.3 mmol), and trimethylborate (4.5 mL, 40 mmol) to afford 2.43 g (99%) of 2,5-dimethoxyphenylboronic acid which was used without further purification.

According to the analysis of related databases, 25245-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 109-85-3, The chemical industry reduces the impact on the environment during synthesis 109-85-3, name is 2-Methoxyethylamine, I believe this compound will play a more active role in future production and life.

Intermediate 13:-[(5-bromo-3-pyridinyl)methyl]-2-(methyloxy)ethanamineA mixture of 3-bromo-5-(chloromethyl)pyridine hydrochloride (500mg, 2.06mmol), 2- (methyloxy)ethanamine (464mg, 6.17mmol), potassium carbonate (284mg, 2.06mmol) in acetonitrile (10ml_) was heated at 80C for 4 hours. Water (10ml_) was added to the cooled reaction mixture and the mixture was extracted with ethyl acetate (2x20ml_). The combined ethyl acetate extracts were evaporated to dryness. The product was purified by ion exchange chromatography using an SCX (sulfonic acid) solid-phase extraction cartridge and eluting with methanol and then with ammonia in methanol (2M) to afford the title compound (452mg, 1.84mmol, 90% yield). LCMS (Method B): Rt 1 .80 minutes; m/z 245,247 (MH+).

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-Methoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ALDER, Catherine Mary; BALDWIN, Ian Robert; BARTON, Nicholas Paul; CAMPBELL, Amanda Jennifer; CHAMPIGNY, Aurelie Cecile; HARLING, John David; MAXWELL, Aoife Caitriona; SIMPSON, Juliet Kay; SMITH, Ian Edward David; TAME, Christopher John; WILSON, Caroline; WOOLVEN, James Michael; WO2011/110575; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 36865-41-5, 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 36865-41-5 as follows.

A mixture of 327 mg (2.00 mmole) OF 7-HYDROXY-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (prepared as detailed in WO 01/77100 utilizing 3-aminophenol in place of 4-aminophenol) and 415 mg (3.0 mmole) of potassium carbonate in 8 ML of CH3CN was heated at reflux for 22 hr. After cooling to room temperature, the mixture was diluted with EtOAc, filtered through celite, and concentrated. Purification by flash column chromatography (SiO2, 20% EtOAc/hexanes gradient to 70% ETOAC/HEXANES) GAVE 380 mg (75%) of 7-BENZYLOXY-3, 4-DIHYDRO-1H-QUINOLIN- 2-one as a white solid. MS : M/Z 254.1 (M+1) 7-BENZYLOXY-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (379 mg, 1.50 mmole) was dissolved in 8 ML of anhydrous DMF under a N2 atmosphere and cooled in an ice bath. NaH (57 mg, 2.24 mmole) was added in a single portion, and the resulting gray suspension was stirred at 0 C for 10 min. 3-BROMO-L-METHOXYPROPANE (275 mg, 1. 8 mmole) was added, and the reaction mixture was stirred at room temperature for 3 hr. Excess hydride was quenched by the addition of a large excess of H2O, and the aqueous layer was extracted with EtOAc (3x). The combined organic layers were washed with H20 (2X) and brine, dried over MGS04, filtered, and concentrated. Purification by flash column chromatography (SIO2, 10% EtOAc/hexanes gradient to 40% ETOAC/HEXANES) provided 382 mg (78%) of 7-BENZYLOXY-L- (3-METHOXYPROPYL)- 3, 4-DIHYDRO-LH-QUINOLIN-2-ONE as a clear viscous oil. MS : M/Z 326.1 (M+1) 7-BENZYLOXY-1- (3-METHOXYPROPYL)-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (355 mg, 1.09 mmole) was dissolved in 50 mL of MEOH and hydrogenated over 0.1 g of 20% Pd/C at 50 psi for 16 hr. The catalyst was removed by filtration through celite, and the solution was concentrated to dryness to afford 259 mg (100%) of 7-HYDROXY-L- (3-METHOXYPROPYL)-3, 4- DIHYDRO-LH-QUINOLIN-2-ONE as a light brown viscous oil which was used without further purification. MS: NIEZ 236. 1 (M+1)

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/89915; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 16452-01-0, name is 3-Methoxy-4-methylaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Step 1: 4-Methyl-3-methoxyphenyl hydrazine. The compound was prepared by a method analogous to that of Example 22, Step 1. The reaction of 100 g (0.73 mole) of 4-methyl-3-methoxyaniline and 50.5 g (0.73 mole) of sodium nitrite in the presence of 330 g (1.46 moles) of stannous chloride dihydrate, 1160 mL of concentrated hydrochloric acid and 250 mL of water gave 58.0 g of product as an 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:
Patent; FMC Corporation; US4702763; (1987); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem