Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, 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 89521-55-1, Recommanded Product: 89521-55-1

107C. 3:1 regio isomeric mixture of tert-butyl 4-(2-amino-3- (benzyloxy)phenylcarbamo vD- 1 -( 1 H-pyrazo Io [3 ,4-d1pyrimidin-4- yl)piperidin-4- ylcarbamate and tert-butyl 4-(2-amino-6-(benzyloxy)phenylcarbamoyl)-l-(lH- pyrazolor3,4-dlpyrimidin-4-yl)piperidin-4-ylcarbamate.N,N-Diisopropylethylamine (6.58 mL, 37.75 mmol) was added in one portion to a stirred suspension o f 4-(tert-butoxycarbonylamino)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4- yl)piperidine-4-carboxylic acid (9.12 g, 25.17 mmol) and O-(7-Azabenzotriazol-l-yl)- N,N,N’,N’-tetramethyluronium hexafluorophosphate (10.53 g, 27.68 mmol) in NMP (60 mL). The mixture was warmed to 5O0C for 15 minutes under nitrogen and cooled to 2O0C. 3-(benzyloxy)benzene-l,2-diamine (5.39 g, 25.17 mmol) was added in one portion and the resulting solution was stirred at 20 0C for 70 hours. The reaction mixture was diluted with EtOAc (200 mL), and washed sequentially with water (3 x 100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product which was purified by flash silica chromatography, elution gradient 1 to 10% MeOH in DCM. Fractions containing product were were evaporated to dryness to afford a pink foam which was shown to be an 82% pure 3:1 regio isomeric mixture of tert- butyl 4-(2-amino-3 -(benzyloxy)phenylcarbamoyl)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4- yl)piperidin-4-ylcarbamate and tert-butyl 4-(2-amino-6-(benzyloxy)phenylcarbamoyl)-l- (lH-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-ylcarbamate. (8.1g, 58% of 82% pure), m/z (ESI+) (M+H)+ = 559; HPLC tR = 2.21 min (28%), 2.41 min (72%); IH NMR (399.9 MHz, DMSO-d6) delta 1.44 (9H, d), 1.96 (0.5H, m), 2.13 (1.5H, s), 3.72 (2H, d), 4.31 (IH, m), 4.46 (IH, m), 4.94 (0.5H, s), 5.13 (1.5H, s), 6.28 (0.25H, d), 6.32 (0.25H, d), 6.51 (0.75H, t), 6.62 (0.75H, s), 6.81 (0.75H, d), 6.90 (0.25H, m), 7.22 – 7.43 (6H, m), 7.50 (1.5H, d), 8.15 (0.25H, s), 8.25 (IH, m), 8.32 (0.75H, s), 8.61 (0.25H, s), 9.10 (0.75H, s), 13.51 (IH, s)

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-(Benzyloxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75109; (2008); 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H6F3NO

General procedure: 1-Aryl-4-nitro-1H-imidazoles were prepared following the general procedure we have developed in our laboratory [23] with some slight modifications. Equimolar amount of aniline derivative was treated with 1,4-dinitro-1H-imidazole in aqueous methanol at ambient temperature in the dark for several hours until complete disappearance of 1,4-dinitro-1H-imidazole monitored by TLC. In some cases, the mixture was heated under reflux to complete the reaction. On cooling, the desired crude 1-aryl-4-nitro-1H-imidazoles separated from the mixture by precipitation. After filtration and recrystallization the pure product was obtained. Yields, solvents used for recrystallization and specific data are given below in the respective sections. Further details are available on request.

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; Trunz, Bernadette Bourdin; Jdrysiak, Rafa?; Tweats, David; Brun, Reto; Kaiser, Marcel; Suwi?ski, Jerzy; Torreele, Els; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1524 – 1535;,
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Application of 29578-83-4,Some common heterocyclic compound, 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, molecular formula is C8H9BrO, 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 1 Synthesis of (1R,10R,11S,16S)-5-methoxy-1,3,11,15,15-pentamethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene Cu(I)I (0.05 g, 0.25 mmol) and NaI (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 min. Anhydrous dioxane (5 mL), N,N’-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and 1-bromo-3-methoxy-5-methylbenzene (1) (1.0 g, 5.0 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110 C. in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2Cl2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (2) (1.05 g, 87% yield) as a pale yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-methoxy-5-methylbenzene, its application will become more common.

Reference:
Patent; Aquinox Pharmaceuticals Inc.; US2011/136802; (2011); A1;,
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Reference of 261762-35-0, 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. 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-benzyloxy-5,6,7,8-tetrahydro-1,6-naphthyridine (500 mg, 2.4 mmol) and 5-bromo-1,2-difluoro-3-methoxy-benzene (696 mg, 3.1 mmol) in dioxane (10 mL) was added tBuONa (345.6 mg, 3.6 mmol), Pd2(dba)3 (44 mg, 0.05 mmol) and RuPhos (34 mg, 0.07 mmol)under N2. After being heated with stuffing at 100 C for 12 hrs, the resulting mixture was filtered and concentrated in vacuo. The residue was purified to give 2-benzyloxy-6-(3,4-difluoro-5- methoxy-phenyl)-7,8-dihydro-5H-1,6-naphthyridine (500 mg), which was used in 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, 5-Bromo-1,2-difluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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Application of 33311-29-4,Some common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, 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.

[00511] To a solution of tert-butyl 3-(2-chloro-5-nitropyrimidin-4-ylamino )phenylcarbamate(1) (430 mg, 1.37 mmol) in THF (10 mL) was added DIEA (530 mg, 4.1 mmol) and 4-(2-methoxyethoxy)aniline (39) (274 mg, 1.64 mmol) at r.t. under N2 atmosphere. The resultingmixture was stirred at r.t. overnight. The solvent was removed and the residue was purified byflash column chromatography (silica gel, 0 to 5% ethyl acetate in PE/DCM (1/1), with 0.5%TEA) to provide tert-butyl 3-(2-( 4-(2-methoxyethoxy)phenylamino )-5-nitropyrimidin-4-ylamino)phenylcarbamate (2) (559 mg, 96%) as a yellow solid. LC-MS (ESI) m/z (M+1) 497.1.

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; YAN, Shunqi; LOURY, David, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; WANG, Longcheng; WO2014/130693; (2014); A1;,
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Reference of 589-10-6, 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. 589-10-6, name is (2-Bromoethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 110 N’-[1-imadazol-1-yl-1-[1-(2-phenoxyethyl)imidazol-2-yl]methylidene]-N,N-dimethylhydrazine (compound Nos. 111, 112) To a solution of ethyl imidazole-2-carboxylate (0.505 g, 3.60 mmol) in N,N-dimethylformamide (6 ml) were added beta-bromophenetole (0.804 g, 4.00 mmol) and potassium carbonate (0.598 g, 4.32 mmol), and the mixture was stirred at 80C for 1 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give ethyl 1-(2-phenoxyethyl)imidazole-2-carboxylate (0.869 g, 3.34 mmol, yield 93%).

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-Bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; EP2168951; (2010); A1;,
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Synthetic Route of 16452-01-0, 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. 16452-01-0 name is 3-Methoxy-4-methylaniline, 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.

A mixture of 0.339 g (2 mmol) 2-Chlorobenzthiazole (commercially available) and 0.275 g (2 mmol) 3-methoxy-4-methylaniline (commercially available) in 4 ml acetic acid was heated to 115 C. for 4 h. After cooling to room temperature the mixture was subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. The product fractions of Benzothiazol-2-yl-(3-methoxy-4-methyl-phenyl)-amine were evaporated to dryness and reacted according to the procedure described for Example 2 with 2-chlorobenzoyl chloride to yield the title compound. MS (m/e): 409.3 (MH+, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Nettekoven, Matthias Heinrich; Roever, Stephan; US2004/266845; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, 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 60876-70-2, HPLC of Formula: C10H13BrO

[3-(4-Benzyloxy)phenoxy]benzo[b]thiophene-2-boronic acid was reacted with 4-(-tertbutoxy)bromobenzene according to the conditions described above for ?2-iodo-3-(4-benzyloxy)[phenoxy]-benzo[b]thiophene and 4-(tertbutoxy)phenyl boronic acid to give [2-(4-tertbutyloxyphenyl)-3-(4-benzyloxy)phenoxy]benzo[b] thiophene in 81% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-(tert-butoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US5856339; (1999); A;,
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Reference of 93919-56-3, 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. 93919-56-3 name is (4-(Trifluoromethoxy)phenyl)methanamine, 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.

(i) N-[4-(Trifluoromethoxy)benzyl]acetamide To a solution of 4-(trifluoromethoxy)benzylamine (3.46 g, 57.6 mmol) in DMF (75 mL) and acetic acid (10.0 g, 52.3 mmol) at -10 C. were added O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (20.2 g, 62.8 mmol) and N,N-diisopropylethylamine (20.0 mL, 115 mmol) and the reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added and the organic phase was washed with water (100 mL), 0.25 M NaOH (100 mL), saturated aqueous NaHCO3 (100 mL), water (100 mL), 0.5 M HCl (100 mL), and water (100 mL), dried over MgSO4, and concentrated in vacuo to afford 11.2 g (92%) of a colourless oil. 1H NMR (600 MHz, CDCl3): delta 2.03 (s, 3H), 4.43 (d, 2H), 5.83 (bs, 1H), 7.17 (d, 2H), 7.31 (d, 2H). 13C NMR (125 MHz, CDCl3): delta 22.9, 42.8, 120.5 (q), 121.1, 129.0, 137.3, 148.4, 170.6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-(Trifluoromethoxy)phenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; Alstermark, Eva-Lotte Lindstedt; Olsson, Anna Christina; Li, Lanna; US2005/282822; (2005); A1;,
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Reference of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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: Catalytic acetic acid was added to a stirred solution of the appropriate formyl pyrimidine (1 eq) (ex: tert-butyl (tert-butoxycarbonyl)(4-((tert-butoxycarbonyl)(p- tolyl)amino)-6-formylpyrimidin-2-yl)carbamate) and the appropriate benzyl amine (1.5 eq) (ex: l-(3-methoxyphenyl)-N-methylmethanamine) in 1 ,2-dichloroethane at 0C then followed by sodium cyanoborohydride (2 eq) was added then the reaction mixture was stirred at room temperature for 16h. After completion of the reaction, the reaction mixture was quenched with minimum amount of saturated sodium bicarbonate solution, the organic product was extracted with dichloromethane (3x). The combined organic extracts were dried over anhydrous sodium sulfate. Solvent was distilled under reduced pressure to give the crude compound. The crude was purified by flash column chromatography (10-20% ethyl acetate/petroleum ether or 2-5% methanol/dichloromethane) to get the desired BOC protected product (ex: tert-butyl (tert-butoxycarbonyl)(4-((tert-butoxycarbonyl)(p- tolyl)amino)-6-(((3-methoxybenzyl)(methyl)amino)methyl)pyrimidin-2-yl)carbamate). (0942) In some examples, the reaction was carried out with trimethyl orthoformate (10 eq) and sodium triacetoxyborohydride (2.5 eq).

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MINORYX THERAPEUTICS S.L.; GARCIA COLLAZO, Ana Maria; BARRIL ALONSO, Xavier; CUBERO JORDA, Elena; REVES VILAPLANA, Marc; ROBERTS, Richard Spurring; (213 pag.)WO2018/122775; (2018); A1;,
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