Tag: M.W=200-300

Application of 1174044-78-0, The chemical industry reduces the impact on the environment during synthesis 1174044-78-0, name is 4-(tert-Butoxy)cyclohexanamine hydrochloride, I believe this compound will play a more active role in future production and life.

(a) 4-((2-(4-tert-butoxypiperidine-1-carbonyl)pyridin-4-yl)methyl)phthalazin-1(2H)-one (73) A solution of 4-tert-butoxypiperidine hydrochloride (227 mg, 1.17 mmol) and triethylamine (0.327 mL, 2.35 mmol) in N,N-dimethlformamide (3 mL) was added in one portion to a stirred solution of 4-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)picolinic acid (5) (300 mg, 1.07 mmol), Triethylamine (0.327 mL, 2.35 mmol) and O-Benzotriazol-1-yl-N,N,N’,N’-tetra-methyluronium hexafluorophosphate (607 mg, 1.60 mmol) in N,N-dimethlformamide (3 mL) at 25 C. The resulting solution was stirred at 25 C. for 4 hours, then The crude mixture was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5mu silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness and lyophilised to afford the desired compound as a solid (250 mg, 55.7% yield); 1H NMR (400.132 MHz, DMSO) delta 1.15 (9H, s), 1.25-1.40 (2H, m), 1.56-1.63 (1H, m), 1.71-1.79 (1H, m), 3.08-3.23 (2H, m), 3.44-3.50 (1H, m), 3.71-3.78 (1H, m), 4.01-4.08 (1H, m), 4.40 (2H, s), 7.39 (1H, dd), 7.48-7.49 (1H, m), 7.83-7.87 (1H, m), 7.90 (1H, td), 7.94-7.97 (1H, m), 8.28 (1H, dd), 8.46-8.48 (1H, m), 12.60 (1H, s); m/z (LC-MS, ESI+), RT=1.67 (M+H 421.5).

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-(tert-Butoxy)cyclohexanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MENEAR, Keith Allan; Javaid, Muhammad Hashim; Gomez, Sylvie; Hummersone, Marc Geoffrey; Lence, Carlos Fenandez; Martin, Niall Morrison Barr; Rudge, David Alan; Roberts, Craig Anthony; Blades, Kevin; US2009/192156; (2009); A1;,
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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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-(Benzyloxy)aniline hydrochloride

To a solution of 6-chloro-5-nitro-nicotinic acid methyl ester (216mg, 1. OMMOL) and 4- benzyloxyaniline hydrochloride (280mg, 1. 2MMOL) in MEOH (LOML) was added PR2NET (0.35mL, 2. 0MMOL). The resulting mixture was stirred at rt overnight, a red solid precipitated from the mixture, which was collected by filtration. MS (ES, Pos. ) : m/z 380 [MH+]. 1H NMR (CDC13, 400 MHz) : 8 = 3.94 (s, 3H), 5.10 (s, 2H), 7.03 (d, J= 8. 8 Hz, 2H), 7.38-7. 46 (M, 5H), 7.50 (d, J= 8. 8 Hz, 2H), 9.01 (d, J= 2.0 Hz, 1H), 9.08 (d, J= 2.0 Hz, 1H), 10.2 (br s, 1H).

The synthetic route of 51388-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2005/21544; (2005); A2;,
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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. 31465-36-8, name is 4-(4-Methoxyphenoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-(4-Methoxyphenoxy)aniline

EXAMPLE 1 In this experiment, 1,3-bis(4-(4-hydroxyphenoxy)phenyl)urea was synthesized utilizing a three step procedure. In the first step of this procedure ethyl(4-(4-methoxyphenoxy)phenyl)carbamate was synthesized by reacting 4-(4-methoxyphenoxy)aniline in the presence of pyridine and ethyl chloroformate according to the following reaction: In the procedure used 23.7 mmol of starting material, 100 ml of DCM and 46.5 mmol of pyridine were combined in a round bottom flask and cooled to a temperature of 0 C. Then 34.8 mmol of ethyl chloroformate was added drop wise over time and maintained at a temperature of 0 C. Then the reaction product was quenched with hydrochloric acid (HCl), dried, concentrated, washed with hexanes solvent, and dried. In this step of the procedure a yield of about 94 percent was attained. In the second step of the procedure was then carried out according to the following reaction scheme where 1,3-bis(4-(4-Methoxyphenoxy)phenyl)urea was made from ethyl(4-(4-Methoxyphenoxy)phenyl)carbamate and 4-(4-Methoxyphenoxy)aniline in the presence of toluene and trimethyl aluminum: In this step of the procedure 4-(4-methoxyphenoxy)aniline was dissolved in toluene (1:25 in toluene) and cooled to a temperature -5 C. Trimethyl aluminum (AlCH3)3 was then added over time under positive nitrogen (N2) pressure with a significant exotherm being experienced). Ethyl(4-(4methoxyphenoxy)phenyl)carbamate was then added as a solid in small portions and heated to a temperature of 80 C. for 8 hours. It was then cooled and quenched with hydrochloric acid (HCl). This step was conducted using caution because the hydrochloric acid generates a significant exothermic reaction and gas formation. The resulting paste was filtered, rinsed with ether and water and was then dried under vacuum with a yield of 79% being attained. The following reaction was carried out as the third and final step of the synthesis procedure wherein the 1,3-bis(4-(4-hydroxyphenoxy)phenyl)urea (U-2EPO) was made from 1,3-bis(4-(4-methoxyphenoxy)phenyl)carbamate in dichloromethane and tetrabromoborane (BBr3):

The synthetic route of 31465-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ruffer, JR., Ronald Q.; (10 pag.)US2016/89919; (2016); A1;,
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Synthetic Route of 17715-69-4,Some common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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: A suspension of Pd2(dba)3 (6.9mg, 0.0075mmol), tBu3PHBF4 (8.7mg, 0.03mmol), KOH (42mg, 0.75mmol), aryl bromide 4 (0.36mmol) and tetralone 3 (0.3mmol) in a mixture of dioxane/water (4:1, v/v, 3mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100¡ãC, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography. Dioxane quality is extremely important for the success of the reaction. Characterization of alpha-aryl-alpha-tetralones is given in Ref.[26].

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-2,4-dimethoxybenzene, its application will become more common.

Reference:
Article; Fernandes, Talita de A.; Costa, Paulo R. R.; Manvar, Dinesh; Basu, Amartya; Kaushik-Basu, Neerja; Domingos, Jorge L. O.; Nichols, Daniel Brian; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 33 – 38;,
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Related Products of 18800-30-1, These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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.

To a solution of 1-bromo-4-(2-bromoethoxy)benzene (19.9 g, 100 mmol; see step (a) above) in THF (120 mL) was portion-wise added t-BuOK (14.0 g, 125 mmol) over 10 min at 0C. After stirring at room temperature for 16 h, the mixture was diluted with ‘water (400 mL) and the product was extracted with light petrol (4×100 mL). The combined organic extracts were washed with brine, dried (Na(at)S04), concentrated and distilled under vacuum to yield the sub-title compound (11.5 g, 58%).

The synthetic route of 18800-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2005/123673; (2005); A1;,
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These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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. Application In Synthesis of 1-(Benzyloxy)-3-bromobenzene

Magnesium strip (1.29 g, 52.8 mmol) in anhydrous THF (50 mL)To the suspension was added iodine which was heated with magnesium.The mixture was refluxed and an approximately 5% solution of 3-bromobenzyl phenol(13.9 g, 52.8 mmol) was added.At the beginning of the reaction, the bromide solution is added dropwise and the mixture is then refluxed again1 hour. The mixture was cooled to about 5 C and a solution of cyclopentanone (4.44 g, 52.8 mmol) in THF (50 mL) was added dropwise. The mixture was stirred at rt for 72 h,The reaction was then quenched with a cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

The synthetic route of 1-(Benzyloxy)-3-bromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; KALAYANOV, GENADIY; TORSSEL, STAFFAN; WAHLING, HORST; (130 pag.)TW2018/15396; (2018); A;,
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Reference of 1112210-82-8,Some common heterocyclic compound, 1112210-82-8, name is 1,3-Dibromo-5-isopropoxybenzene, molecular formula is C9H10Br2O, 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.

Synthesis of Intermediate 2)Molecular Weight: 293.98 Molecular Weight: 186.21[00530] In a 3-neck 100 mL round-bottomed flask, intermediate- 1 (3.5 g, 1 eq.) was dissolved in DMF and degassed it for 20-30 min. To this reaction mixture, Zinc Cyanide (1.72 g, 1.2 eq.) and tetrakis (0.705 g, 0.05 eq.) was added. Resulting reaction mixture was stirred at 80-90C and reaction was monitored by TLC using Ethyl acetate: hexane (1 :9) as mobile phase, which shows starting material was consumed after 5 h. Reaction was quenched into ice-water slurry and compound was extracted using ethyl acetate (50 mL x 3), combined organic layer were dried over anhydrous sodium sulfate and concentrated under reduce pressure to give crude compound. The crude material was subjected to column chromatography using silica 60/120 as stationary phase and ethyl acetate :n-Hexane as mobile phase. Compound was eluted in 7% ethyl acetate in Hexane. Fractions containing compound was distilled out using rotary evaporation at 40 C/250 mm Hg to obtain 2.095 g (94.51%). Mass/LCMS: LC-MS purity 92.36%, NMR: Confirmed.

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

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SHECHTER, Sharon; KAUFFMAN, Michael; SANDANYAKA, Vincent, P.; SHACHAM, Sharon; WO2011/109799; (2011); A1;,
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Some common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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. name: 4-Bromo-2-methoxyaniline

a) tert-Butyl N-(4-bromo-2-methoxyphenyl)carbamate. A mixture of 4-bromo-2-methoxyaniline (34.0 g, 0.17 mol) and di-tert-butyl dicarbonate (44.5 g, 0.20 mol) in tetrahydrofuran (350 ml) was heated at reflux for 22 h. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (350 ml) and washed with 1 N citric acid (200 ml), dried over magnesium sulfate, filtered and evaporated to give tert-butyl N-(4-bromo-2-methoxyphenyl)carbamate as a yellow oil (80% pure, 57.10 g, 0.15 mol): 1H NMR (DMSO-d6, 400 MHz) delta 8.01 (s, 1H), 7.63 (d, 1H), 7.17 (d, 1H), 7.07 (dd, 1H), 3.82 (s, 3H), 1.45 (s, 9H); TLC (n-heptane/ethyl acetate=2:1) Rf 0.67.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59557-91-4, its application will become more common.

Reference:
Patent; CALDERWOOD, DAVID; ARNOLD, LEE; MAZDIYASNI, HORMOZ; HIRST, GAVIN C.; DENG, BOJUAN B.; JOHNSTON, DAVID N.; RAFFERTY, PAUL; TOMETZKI, GERALD B.; TWIGGER, HELEN L.; MUNSCHAUER, RAINER; US2003/187001; (2003); A1;,
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Reference of 36805-97-7, 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 36805-97-7 as follows.

1 ,1-Di-tert-butoxy-W,A/-dimethylmethanamine (1.03 ml, 4.30 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1 -ethyl-1 H-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 39 (380 mg, 1.08 mmol) in toluene (10 ml). The reaction was heated at 80 C for 2 h then allowed to cool to RT. 1 ,1-Di-tert-butoxy-A/,/v- dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 80 C for 3 h then allowed to cool to RT. 1 ,1-Di-terf-butoxy-A/,W-dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 110 C for 1 h then allowed to cool to RT. The reaction mixture was diluted with EtOAc (20 ml) then washed with water (2 x 20 ml), saturated aq. NaHC03 solution (2 x 20 ml) and brine (10 ml), then dried over Na2S04, filtered and evaporated to afford an orange solid (510 mg). The crude material was purified by flash column chromatography on a silica column (25 g). The column was eluted with EtOAc: heptane, increasing the gradient linearly from 0:100 to 50:50 over 10 column volumes. The desired fractions were combined and evaporated to yield the product as a white solid (320 mg, 72%).1H NMR (500 MHz, DMSO-de) delta 8.07 (s, 1 H), 7.98 (t, J = 5.8 Hz, 1 H), 7.77 (dd, J = 8.4, 1.3 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.41 – 7.12 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 5.9 Hz, 2H), 4.38 – 4.24 (m, 2H), 1.58 (s, 9H), 1.29 (t, J = 7.1 Hz, 3H). LC/MS (System A): m/z (ESI+) = 4 0 [MH+], R, = 1.17 min, UV purity = 99%.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, 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 24988-36-1, Computed Properties of C8H8Br2O2

2,4-dibromo-1,5-dimethoxybenzene (88.8 g, 300 mmol), 2-fluorophenyl boric acid (100.7 g, 720 mmol), 2 M aqueous solution of Na2CO3 (600 mL), Pd[PPh3]4 (6.73 g, 6 mmol), DME (150 mL), and toluene (150 mL) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 36 hours. After the completion of the reaction, the obtained solution was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with toluene. The extract was dried with MgSO4, and was then filtered and concentrated. The resultant sample was purified by silica gel column chromatography. The purified product was concentrated to dryness, and was then recrystallized, whereby a white solid was obtained in an amount of 86.5 g in 88% yield. FD-MS analysis C20H16F2O2: theoretical value 326, observed value 326

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; Idemitsu Kosan Co., Ltd.; EP2301926; (2011); A1;,
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