Author: Jessica.F

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;,
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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;,
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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;,
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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;,
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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;,
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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. 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;,
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Synthetic Route of 24332-20-5, 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. 24332-20-5, name is 1,1,2-Trimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1,1,2-trimethoxyethane (132 mg, 0.46 mmol) in H2O (1 mL), was added TFA (1 mL). The reaction mixture was stirred at 50 for 5 min. The resulting colorless solution was used as such in the following step.

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

Reference:
Patent; REMEDY PLAN, INC.; CRIMMINS, Gregory, Thomas; DE JESUS DIAZ, Dennise, Alexandra; BHURRUTH-ALCOR, Yushma; (483 pag.)WO2019/213570; (2019); A1;,
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Related Products of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

Hexadecanedioic acid (4.5 g, 15.71 mmol) was suspended in Toluene (28.1 ml) and the mixture was heated to reflux. 1,1 -di-tert-butoxy-N,Ndimethylmethanamine (10.10 ml, 42.1 mmol) was added drop-wise over 30 mm. Themixture was reflux overnight. The solvent was removed in vacuo at 50C and the crude material was suspended in CH2C12/EtOAc (75 mL. 1:1) ans stirred for 15 mm. The solids were removed by filtration and washed with CH2C12 (25 mL). The filtration was evaporated in vacuo. The resulting material was suspended in CH2C12 (6 mL), cooled with ice for 10 mins, and filtered. The solvent was removed invacuo to leave crude product which was purified by flash chromatography (silic gel,EtOAc/Hexane) to get 16-(tert-butoxy)-16-oxohexadecanoic acid (2.56 g, 7.47 mmol,47.6 % yield). Analysis condition D: Retention time = 5.04 mm; ESI-MS(+) m/z269.3 [M – OC(CH3)3]; ?H NMR (500MHz, METHANOL-d4) oe 2.33 – 2.18 (m, 4H),1.66 – 1.54 (m, 4H), 1.50 – 1.43 (m, 9H), 1.40 – 1.25 (m, 20H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILLMAN, Kevin W.; GOODRICH, Jason; BOY, Kenneth M.; ZHANG, Yunhui; MAPELLI, Claudio; POSS, Michael A.; SUN, Li-Qiang; ZHAO, Qian; MULL, Eric; GILLIS, Eric P.; SCOLA, Paul Michael; LANGLEY, David, R.; (683 pag.)WO2016/77518; (2016); A1;,
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Reference of 366-99-4, A common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

Step 1. To a mixture of 3-fluoro-4-methoxyaniline (3.00 g, 21.3 mmol) and paraformaldehyde (1.28 g, 42.5 mmol) in MeOH (100 mL) was added sodium methoxide (19.4 mL, 85.0 mmol) and the reaction mixture mixture was sealed and heated at 55 °C for 2 h. After cooling to rt, sodium borohydride (2.01 g, 53.1 mmol) was added in small portions. The final reaction mixture was stirred at rt overnight. The solvent was removed in vacuo and the residue was taken up in EtOAc (100 mL) and washed with water (150 mL). The separated aqueous component was saturated with NaCl, extracted with EtOAc (100 mL) and the combined organic components were washed with brine (50 mL), dried over MgS04, filtered, and concentrated in vacuo. The residue was taken up into DCM (10 mL) and purified by FCC (80 g silica gel cartridge), eluting with gradient 5percent~50percent EtO Ac- hexanes to afford 3-fluoro-4-methoxy-N-methylaniline (3.08 g) as a light yellow oil. LC- MS retention time = 1.34 min; m/z = 153.42 [M-H]-. (Start percent B = 0, Final percent B = 100, Gradient Time = 2 min, Flow Rate = 1 ml/min, Wavelength = 220, Solvent Pair = Water: Acetonitrile 10 mM Ammonium Acetate, Solvent A = 95percent Water: 5percent Acetonitrilel 10 mM Ammonium Acetate, Solvent B = 5percent Water: 95percent Acetonitrile 10 mM Ammonium Acetate, Column = Phenomenex Luna CI 8 2.0 X 30mm 3um, MW1 = 132+/- Oven Temp. = 40 °C).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 54314-84-0

The reaction mixture of 28 (0.50 g, 1.5 mmol) and [(3-bromopropoxy)methyl]benzene (32) (0.44 ml, 2.5 mmol) in dry 1,4-dioxane (16 ml) was stirred for 5 days to afford the title compound as a white solid in 73% yield (0.62 g). mp: 228-229 C; 1H-NMR (400 MHz, DMSO-d6): delta = 7.27-7.40 (m, 15H), 6.76 (s, 1H), 5.21 (br, 1H), 4.46 (s, 2H), 3.85 (m, 1H), 3.46 (t, J = 5.8 Hz 2H), 3.21-3.39 (m, 6H), 3.03 (m, 1H), 2.25 (m, 1H), 1.49-1.95 (m, 6H); 13C-NMR (500 MHz, DMSO-d6): delta = 172.8, 158.9, 143.6, 143.5, 130.1, 128.5, 128.4, 128.2, 128.1, 127.6, 127.5, 121.1, 115.0, 81.3, 69.1, 67.0, 63.0, 59.8, 54.1, 53.2, 26.2, 23.9, 20.9, 19.0, 18.1; HRMS calcd. for C31H36N1O4 [M]+: 486.2644; found: m/z = 486.2663; HPLC (Method B): tR (min) = 15.2 (98%).

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:
Article; Yamashita, Yasunobu; Tanaka, Ken-ichiro; Yamakawa; Asano; Kanda, Yuki; Takafuji; Kawahara, Masahiro; Takenaga, Mitsuko; Fukunishi, Yoshifumi; Mizushima; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3339 – 3346;,
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