Month: March 2021

Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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. HPLC of Formula: C13H11BrO

.2 eq BuLi in hexane,1.2 eq TMEDA, 8 eq SO2 in Et2O, 3 eq N-chlorosuccinimide, EtjO, -75 C to 25 C, then dioxane, aq NH3. 250C1 16 hA solution of l-benzyloxy-3-bromobenzene (28.3 g) in Et2O (375 mL) is cooled to – 70 C and treated with TMEDA (19.2 mL) and tt-BuLi in hexane (1.6 M, 79 mL). The solution is stirred at -70 C for 1 h and transferred into a cooled solution (-70 0C) of SO2 (54.4 g) in Et2O (375 mL). The mixture is kept at -700C for 15 minutes, then allowed to warm to RT over 1 h. The solvent is evaporated and the residue is suspended in aqueous sodium phosphate (IM, 750 mL, pH 6). EtOAc (500 mL) is added and the solution is cooled to 00C. JV-Chlorosuccinimide (43.5 g) is slowly added and the pH is readjusted to pH 6 by addition OfNa3PO4. The reaction mixture is stirred vigorously for 1 h. The phases are separated and the aqueous phase is extracted twice with EtOAc. The combined organic phases are washed with H2O and brine, dried and concentrated to give a yellowish oil. The residue is taken up in dioxane (400 mL) and NH3 in H2O (28%, 200 mL) is added. The reaction mixture is stirred for 12 h and then concentrated to dryness. The residue is chromatographed on SiO2 gel (eluent hexanes/EtOAc 4:1 to 3:7) to give 3-benzyloxy- benzenesulfonamide as a white powder. API-MS: M-I ?= 262.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53087-13-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2007/120595; (2007); A2;,
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Reference of 216067-66-2, The chemical industry reduces the impact on the environment during synthesis 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, I believe this compound will play a more active role in future production and life.

Example 5 5-(N-Benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-hydroxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione To a solution of the compound obtained in Reference Example 6 (2.0 g, 3.36 mmol) in dichloromethane (40 ml) was added triethylamine (0.94 ml, 6.73 mmol) with ice-cooling, followed by stirring. Then, N,N’-carbonyldiimidazole (1.09 g, 6.73 mmol) was added to the reaction mixture with ice-cooling. The reaction mixture was allowed to warm to room temperature and was stirred for 24 hours. The reaction mixture was ice-cooled again and O-(2,4-dimethoxybenzyl)hydroxylamine (3.11 g, 16.98 mmol) was added. The reaction mixture was then allowed to return to room temperature and stirred for 19 hours. This reaction mixture was partitioned between chloroform and saturated aqueous sodium hydrogencarbonate solution and the aqueous layer was extracted with chloroform. The extracts were combined, washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure. To a solution of the residue in dichloromethane (50 ml) was added trifluoroacetic acid (5 ml), followed by stirring at room temperature for 20 minutes. This reaction mixture was partitioned between chloroform and saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted with chloroform. The extracts were combined, washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel to give white amorphous powder, which was recrystallized from chloroform-ether to give the title compound as white crystals (2.2 g, 100%). mp: 164-165 C.; 1H-NMR (300 MHz, CDCl3) delta: 2.05 (3H, s), 3.46 (2H, s), 3.92 (2H, s), 5.35 (2H, s), 6.65(1H, br), 6.90 (2H, t, J=8.0 Hz), 7.28-7.65 (15H, m), 8.04 (1H, s), 9.73 (1H, br). IR (KBr): 3326, 2856, 1715, 1665, 1628, 1591, 1531, 1468 cm-1. FAB-Mass m/z 654(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, O-(2,4-Dimethoxybenzyl)hydroxylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6297379; (2001); B1;,
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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 6298-96-0 as follows. Safety of 1-(4-Methoxyphenyl)ethylamine

To 11.0 g (72.7 mmol) (S)-1-(4-methoxy-phenyl)-ethylamine is added carefully 30 mL HBr (30% in HOAc). The mixture is stirred at 100 C for 4 h. After cooling down to r.t., the solvent is removed in vacuo and the residue is dried in vacuo. The resultingproduct is used without further purification.C6H11NO*HBr (M= 218.1 g/mol)ESI-MS: 121 [M+H-NH3]+ Rt (HPLC): 0.50 min (method A)

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; ROTH, Gerald Juergen; NOSSE, Bernd; HEINE, Niklas; WO2013/92616; (2013); A1;,
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Related Products of 39538-68-6, 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. 39538-68-6, name is 2-Methoxy-4-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a magnetically stirred ice-bath cooled solution of the selected succinic monoamide derivative (4 mmol) in anhydrous dioxane (20 ml) neat oxalyl chloride was added (8 mmol). After stirring over 30 min the reaction mixture was warmed to room temperature. Two hours later, the reaction mixture was re-cooled to 0 C in ice bath followed by drop wise addition of the particular aromatic amine (4 mmol) in pyridine (10 mL) to the reaction mixture. After stirring over 30 min the reaction mixture was warmed to room temperature and allowed to stir over 24 h. Subsequently, the reaction was carefully quenched with saturated sodium bicarbonate solution (200 mL). Finally, the mixture was filtered to offer the products as whitish to gray solids that were re-crystallized from acetone (see Scheme 2).

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

Reference:
Article; Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4746 – 4771;,
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Synthetic Route of 1535-75-7, 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Added the 1 -methylethyl 2-{4-[(4-bromophenyl)methyl]-1 -pi perazinyl}-3-pyrid me carboxylate (25.0 mg, 0.060 mmol), Anilines (0.120 mmol), Xphos (5.7 mg, 0.012 mmol), potassium phosphate (38.1 mg, 0.179 mmol) and palladium(ll) acetate (1.34mg, 10 mol%) in 3.0 mL Toluene in a 5 mL reaction vial, and then stirred the mixture for 30mm at room temperature under nitrogen atmosphere. The stirring was kept for 12 hr at 105 C. Pretreated a StratoSpheres PL-Thiol MP SPE column with methanol, filtered reaction mixture through column, washed with Methanol. Concentrated to give the crude product, which was dissolved in DMSO, and purified on a Gilson HPLC (XBridge 19 x 100mm 5u preparatory column), eluting at 18 mLmin with a linear gradient running from 20% to 95% acetonitrile and 0.1% aqueous NH4OH over 18 mm. The desired fractions were concentrated under a stream of nitrogen at 45 C, giving the desired product (12.83 mg, 41.7%).LCMS: mz= 515.0 [M+H], Ret. Time: 1.16 mm.

The synthetic route of 2-(Trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BOEHM, Jeffrey, Charles; DAVIS, Roderick, S.; KERNS, Jeffrey; LIN, Guoliang; MURDOCH, Robert, D.; NIE, Hong; WO2013/6596; (2013); A1;,
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Application of 54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 1-[2-(2-methoxy-ethoxy)-ethyl]-5-nitro-1,2-dihydro-indazol-3-one A mixture of 5-nitro-1,2-dihydro-indazol-3-one (399 mg, 2.22 mmol), 1-bromo-2-(2-methoxy-ethoxy)-ethane (454 muL, 3.34 mmol), potassium iodide (370 mg, 2.22 mmol) and 1N sodium hydroxide solution (6.7 mL, 6.7 mmol) in 2 ml dioxane was stirred at 60 C. overnight. The reaction mixture was then cooled, poured into 50 mL H2O and 300 L 10N NaOH was added. The aqueous layer was extracted with CH2Cl2 and then acidified to ~pH 2 with 6N aqueous HCl. The aqueous layer was extracted with ethyl acetate. The combined organic layer dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography to afford the product 1-[2-(2-methoxy-ethoxy)-ethyl]-5-nitro-1,2-dihydro-indazol-3-one (380 mg, 61%). ES-MS calcd for C12H15N3O5 (m/e) 281.26, obsd 282.17 (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, 1-Bromo-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bolin, David Robert; Cai, Jianping; Goodnow, JR., Robert Alan; US2009/163546; (2009); A1;,
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Synthetic Route of 701-56-4, These common heterocyclic compound, 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, 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.

General procedure: To a screw-capped tube (5 mL) containing freshly distilled MeCN (2.0-3.0 mL) was successively added CoCl2 (0.10 equiv for N-substituted maleimide), an aromatic tertiary amine (2.0 equiv for N-substituted maleimide), an N-substituted maleimide (0.50-1.0 mmol), and 5.5 M TBHP in decane solution (1.5 equiv for N-substituted maleimide) under N2 atmosphere. After the tube was sealed with a cap that contained a PTFE septum, the resultant mixture was stirred at 60 C (bath temperature). After cooling to room temperature, the mixture was passed through a silica gel-packed short column (EtOAc as the eluent), and the filtrate was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane : EtOAc =5 : 1) to give the corresponding tetrahydroquinoline derivative. If necessary, the isolated product was further purified by a preparative HPLC equipped with a GPC column (chloroform as the eluent).

The synthetic route of 701-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakai, Norio; Matsumoto, Shun; Ogiwara, Yohei; Tetrahedron Letters; vol. 57; 49; (2016); p. 5449 – 5452;,
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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. 136-90-3, name is 4-Methoxy-3-methylphenylamine, A new synthetic method of this compound is introduced below., SDS of cas: 136-90-3

Compound 107 3-[[(3S)-tetrahydrofuran-3-yl]sulfamoyl]benzoic acid (270 mg, 1.0 mmol) was dissolved in dichloromethane (5 mL). 3-methyl-4-methoxyaniline (165 mg, 1.2 mmol) and triethylamine (145 mg, 1.4 mmol) were added to the mixture at 20C. The mixture was stirred at 20C for 5 minutes. HATU (456 mg, 1.2 mol) was added and the mixture was further stirred at 20C for 8 hours. The solvent was removed in vacuo and the obtained residue was purified by high performance liquid chromatography (Column: Phenomenex Synergi C18 150*20mm*5um.. A: H2O+0.1%TFA B: MeCN from 30% to 60 % B in A). The product fractions were collected and the organic solvent was evaporated in vacuo. The aqueous layer was neutralized with saturated aqueous NaHCC>3 and extracted with dichloromethane (2 x 10 mL). The combine organic layers was dried over Na2S04 and concentrated in vacuo resulting in compound 107 (135 mg). Method A; Rt: 5.24 min. m/z : 391.3 (M+H)+ Exact mass: 390.1

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; JANSSEN R&D IRELAND; LAST, Stefaan, Julien; RABOISSON, Pierre, Jean-Marie, Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; WO2014/33176; (2014); A1;,
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Reference of 658-89-9, The chemical industry reduces the impact on the environment during synthesis 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

Intermediate 51 : Mixture of (trans)-N-{2-amino-4-[(trifluoromethyl)oxy1phenyl)-3-(6-methyl- 2-pyridinyl)-2-oxo-1-oxa-3-azaspiro[4.51decane-8-carboxamide and (trans)-N-{2-amino-5- [(trifluoromethyl)oxy1phenyl)-3-(6-methyl-2-pyridinyl)-2-oxo-1-oxa-3-azaspiro[4.51decane- 8-carboxamide; To a shaken mixture of (trans)-3-(6-methyl-2-pyridinyl)-2-oxo-1-oxa-3- azaspiro[4.5]decane-8-carboxylic acid (Intermediate 52, 65.4 mg, 0.225 mmol) and 4- [(trifluoromethyl)oxy]-1 ,2-benzenediamine (Intermediate 32, 64.9 mg, 0.338 mmol) in pyridine (1.5 ml) was added EDCHCI (86 mg, 0.451 mmol) and the mixture was shaken for 2 hours. The mixture was concentrated under vacuum; the residue was partitioned between saturated sodium bicarbonate solution and EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under vacuum to give a residue. The residue was purified twice by silica gel chromatography (elution in gradient with 0-100% Et2ODCM) to afford the title compound as brown residue (98 mg, 80%). No further purification followed. UPLC-MS: 0.76 min, m/z 465 [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-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
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5397-31-9, name is 3-((2-Ethylhexyl)oxy)propan-1-amine, 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. Safety of 3-((2-Ethylhexyl)oxy)propan-1-amine

Example 13A reaction vessel was charged with 180 parts by weight of 3-(2-ethylhexyloxy)propylamine, 180 parts by weight of DL-4,4-dimethyl pyroglutamine acid, and 100 parts by weight of methanol, and the mixture was stirred at 70 C. for 3 hours. The resulting reaction mixture was stripped at 90 C. under reduced pressure to remove the methanol, and 335 parts by weight of white solid was obtained at a yield of 93%. Results of the 13C-NMR shown in Table 13, below, and absorption at 1685 cm-1 (from amide bond) in the measurement of IR spectrum confirmed that the resulting product was an amino acid compound represented by the following formula: TABLE 13 13C-NMR (CDCl3) 11.2~74.3ppm (CH, -CH2-, -CH3) 180.9ppm (-NH-CO-) 35.0ppm (-CO-C) 22.4ppm (C-CH3) 41.8ppm (-C-CH2-) 56.4ppm [-CH(NH2)(COOH)] 179.2ppm (-COOH)

The synthetic route of 5397-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MORIYA, Hiroyuki; US2011/144369; (2011); A1;,
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