Month: May 2021

Reference of 2009-83-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 2009-83-8, name is 6-Chlorohexan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

I-a-4-3) (6 g, 43 mmol) p-hydroxybenzoic acid, (7.1 g, 52 mmol) chlorohexanol, (3.44 g, 86 mmol) sodium hydroxide,(0.7g, 4.3mmol) potassium iodide and 50mL water were added to a three-necked flask, heated to reflux, and refluxed for 4 hours,The temperature was lowered, hydrochloric acid was added to the reaction solution, the reaction solution was filtered, and the filter cake was recrystallized twice from ethyl acetate to obtain (6.1 g, 26 mmol) in a yield of 60%

According to the analysis of related databases, 2009-83-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shijiazhuang Cheng Zhiyonghua Display Materials Co., Ltd.; Zhao Lei; Meng Jingsong; Li Ming; Wei Tianyu; Yuan Guoliang; Liang Zhian; (27 pag.)CN110551078; (2019); A;,
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Reference of 5344-90-1 ,Some common heterocyclic compound, 5344-90-1, molecular formula is C7H9NO, 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.

A. 2-Amino-5-bromobenzyl alcohol (1a): A solution of 12.316 g (0.1 mol) of 2-aminobenzyl alcohol in 300 mL of dry ether was treated at about 0° C. with 40.97 g (0.1 mol) of 2,4,4,6-tetrabromocyclohexa-2,5-dienone added in portions with vigorous stirring. Stirring was continued for about 1 hour at about 0° C., then the mixture was extracted twice with dilute HCl. The combined acid extracts were washed with ether and the ether was discarded. The acid solution was made alkaline with NaOH and extracted with fresh ether. The ether extracts were washed with water, brine, dried (Na2 SO4) and concentrated to afford 17.86 g (88percent) of 1a, mp 107-110° C. 1 H NMR (CDCl3): d=7.22-7.17 (m, 2 H); 6.57 (d, 1 H); 4.61 (s, 2 H). (MS (El): m/z=201, 203 (M+, Br isotopes).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5344-90-1, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5843972; (1998); A;,
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Related Products of 145691-59-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 145691-59-4, name is (3,5-Dibromophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

(3,5-Dibromophenyl)methanol (10 g, 37.60 mmol, 1 eq) was dissolved in anhydrous DCM (100 mL) in a dried flask under nitrogen. The reaction mixture was cooled to 0°C and stirred under nitrogen atmosphere. DIEA (9.72 g, 75.21 mmol, 13.10 mL, 2 eq) was added drop wise to the above solution, after 10 minutes of stirring at 0°C, MsCl (6.46 g, 56.41 mmol, 4.37 mL, 1.5 eq) was added drop-wise to the above reaction mixture. Finally, the reaction mixture was allowed to stir at 26°C for 2hrs. TLC (Petroleum ehter : EtOAc = 5:1, uv & stained by KMnO4) showed starting alcohol was consumed up and two new spots were formed. Reaction mixture was washed with water (80 mL) followed by NaHCO3 (80 mL) solution and brine (80 mL), dried over anhydrous Na2SO4, filtered and evaporated to dryness to give the desired product as a brown liquid (12.11g). The above liquid was used directly for the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 3.04 (s, 3 H) 4.49 (s, 2 H) 5.16 (s, 2 H) 7.48 (d, J=1.76 Hz, 2 H) 7.50 (d, J=1.76 Hz, 2 H) 7.63 (t, J=1.76 Hz, 1 H) 7.70 (t, J=1.76 Hz, 1 H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 145691-59-4, (3,5-Dibromophenyl)methanol.

Reference:
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
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Related Products of 7735-42-4 ,Some common heterocyclic compound, 7735-42-4, molecular formula is C16H34O2, 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.

The diol (1 eq.) and 100 mL acetonitrile were placed in a 200 mL beaker with a stirring element. The mixture was re-heated to a temperature of 50C, after which copper complex [Cu(MeCN)4]PF6 (10 mol%), TEMPO (10 mol%) 2,2′-bipyridyl (10 mol%) and 1 -methylimidazole (20 mol%) were added one by one. The reaction was conducted for 4 hours until the substrate disappeared. Afterwards, the whole was evaporated and dissolved in methylene chloride, and SnachCat solution was then added. After stirring, the solution was filtered (through Si02), washing it with methylene chloride, and then the solution was evaporated. (0814) Hexyl triphenylphosphine bromide (2.1 eq.) was dissolved in 120 mL tetrahydrofuran under the atymosphere of argon in a 250 mL single-necked round flask. 2.5M solution of n-butyllithium in hexane (2.1 eq) was added dropwise to the resulting mixture, and allowed to rest while stirring for 30 minutes. The resulting solution was cooled to 0C, and the previously obtained aldehyde in a solution of tetrahydrofuran (1 eq.) was slowly added dropwise. The reaction mixture was heated to room temperature and then stirring was continued for another 2 hours at room temperature. 50 mL of saturated ammonium chloride solution was then added. The mixture was washed four times with methylene chloride. The combined ether layers were dried over MgS04. The product was purified by chromatography using n- hexane. A colourless oil was obtained. 75% yield. (0815) 1 H NMR (400 MHz, CDCI3) 5.46 – 5.27 (m, 4H), 2.10 – 1 .90 (m, 8H), 1 .44 – 1 .16 (m, 36H), 0.97 – 0.80 (m, 6H); 13C NMR (101 MHz, CDCI3) delta 130.05, 130.04, 31 .69, 29.93, 29.85, 29.82, 29.73, 29.62, 29.48, 27.36, 27.33, 22.75, 14.25

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. 7735-42-4, 1,16-Hexadecanediol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIWERSYTET WARSZAWSKI; GRELA, Karol; CZARNOCKA-?NIAD?A, Sylwia; SYTNICZUK, Adrian; MILEWSKI, Mariusz; URBAN, Mateusz; BANACH, ?ukasz; D?BROWSKI, Micha?; (109 pag.)WO2018/197963; (2018); A1;,
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Electric Literature of 39895-56-2, 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 39895-56-2 as follows.

1-Methyl-4-piperidone (84 muL, 0.73 mmol) was dissolved in methanol (5 mL) and 4-(aminomethyl)benzylalcohol (57MBT52B) (100 mg, 0.73 mmol) was added followed by acetic acid (125 muL). NaBH3CN (92 mg, 1.46 mmol) was added and the mixture was stirred for 3 h. The reaction mixture was evaporated and 2M NaOH (5 mL) was added. Extraction with CH2Cl2 (4*5 mL), drying with Na2SO4 and evaporation gave 152 mg (87%) of N-((4-(hydroxymethyl)phenyl)methyl)-4-amino-1-methylpiperidine (57MBT56D) as a white solid. HPLC-MS (method B) showed MH+=235. UV/MS (%)=100/100.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39895-56-2, its application will become more common.

Reference:
Patent; ACADIA Pharmaceuticals Inc.; ANDERSSON, Carl-Magnus A.; CROSTON, Glenn; HANSEN, Eva Louise; ULDAM, Allan Kjaersgaard; US2015/259291; (2015); A1;,
Alcohol – Wikipedia,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.16700-55-3, name is (2,6-Dimethoxyphenyl)methanol, molecular formula is C9H12O3, molecular weight is 168.1898, as common compound, the synthetic route is as follows.Computed Properties of C9H12O3

Step A: Preparation of Ethyl 2-(3-(2,6-Dimethoxybenzyloxy)phenyl)acetate:; A solution of 2,6-Dimethoxylbenzyl alcohol (3.33 g, 19.8 mmol) and diisopropyl azodicarboxylate (DIAD, 4.36 g, 21.6 mmol) in THF (30 ml) was added drop wise to a solution of Ethyl 2-(3-hydroxyphenyl)acetate (4 g, 22.2 mmol) and triphenylphosphine (5.66g, 21.6 mmol) in THF (80 ml). The reaction mixture was stirred at room temperature for 8 hours, diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1) to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16700-55-3, (2,6-Dimethoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; WELLSTAT THERAPEUTICS CORPORATION; WO2009/151695; (2009); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 86770-74-3, 2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethanol, 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, Computed Properties of C8H19NO4, blongs to alcohols-buliding-blocks compound. Computed Properties of C8H19NO4

To a solution of 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethanol (0.50 g, 2.6 mmol) was added BCN-OSu (29-1 , 0.69 g, 2.3 mmol) and Et3N (0.97 ml_, 0.70 g, 7.0 mmol). The resulting mixture was mixture was stirred for 80 min and saturated aqueous NH4CI (60 ml_) was added. After separation, the aqueous phase was extracted with DCM (60 ml_). The combined organic layers were dried (Na2SC>4) and concentrated. The residue was purified with silica gel chromatography (DCM 10% MeOH in DCM), which yielded 578 mg (1.56 mmol, 67%) of the desired product. 1 H NMR (400 MHz, CDCIs) d (ppm) 5.98-5.85 (bs, 1 H), 4.14 (d, J = 8.0 Hz, 2H), 3.78-3.59 (m, 12H), 3.58-3.52 (m, 2H), 3.42-3.32 (m, 2H), 3.19-3.06 (bs, 1 H), 2.35-2.16 (m, 6H), 1 .70-1.50 (m, 2H), 1.36 (quintet, J = 8.6 Hz, 1 H), 0.99-0.87 (m, 2H).

The synthetic route of 86770-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNAFFIX B.V.; VERKADE, Jorge Merijn Mathieu; HOOGENBOOM, Jorin; VAN BERKEL, Maria Antonia; VAN DELFT, Floris Louis; (95 pag.)WO2019/110725; (2019); A1;,
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Synthetic Route of 23377-40-4, 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. 23377-40-4, name is 3-(Hexadecyloxy)propan-1-ol, molecular formula is C19H40O2, The 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.

l-O-Hexadecyl^-deoxy-S-O-iS’^’-O-diacetyl^’-N-phthalimido-S’-azido-Z e’- dideoxy- -D-glucopyranosyl)-sn-glycerol (35)Compound 30 (0.4 mmol) and the previously reported lipid compound 34 (168 mg, 0.48mmol) were dissolved in anhydrous DCM (10 ml) under argon atmosphere. NIS (180 mg, 0.8 mmol) and silver triflate (20 mg, 0.08 mmol) were added. The reaction mixture was left under vigorous stirring for 3 hrs. At the completion of reaction (TLC monitoring), the reaction mixture was diluted by DCM (20 ml) and then filtered over Celite. The resulting organic layer was washed with saturated sodium thiosulphate solution (2 times), saturated sodium bicarbonate (3 times) and water (2 times). The organic layer was then dried over anhydrous Na2S04 and then concentrated under vacuum to give a brownish gel residue. The residue was then purified by flash chromatography (Hexane/Ethyl acetate, 4:6) to give compound 35 as a white solid. Yield 51%. (0265) 1H NMR (300 MHz, Chloroform-d) delta = 7.85 (dd, J=5.5, 3.1 , 2H, phthalimido aromatic protons), 7.73 (dd, J=5.5, 3.1 , 2H, phthalimido aromatic protons), 5.79 (dd, J=10.8, 9.0, 1 H, H-3), 5.38 (d, J=8.5, 1 H, H-1), 5.05 (dd, J=10.1 , 9.0, 1 H, H-4), 4.30 (dd, J=10.8, 8.5, H, H-2), 3.96 – 3.81 (m, 2H), 3.63 – 3.52 (m, 1 H), 3.43 (dt, J-13.6, 6.9, 1 H), 3.28 – 3.16 (m, 3H), 3.15 – 2.99 (m, 2H), 2.03 (s, 3H, Acetate CH3), 1.85 (s, 3H, Acetate CH3), 1.76 – 1.58 (m, 2H), 1.26 (s, 26H, Lipid tail), 0.89 (t, J = 6.6 Hz, 3H, lipid terminal -CH3).13C NMR (75 MHz, CDC13) delta = 170.12, 169.62, 134.27, 123.57, 97.99, 73.60, 71.82, 71.00, 70.53, 70.37, 67.04, 66.96, 54.68, 51.24, 31.91 , 29.73, 29.68, 29.59, 29.48, 29.34, 26.07, 22.67, 14.10.ES-MS: calcd: m/z: 723.4, found [M+Na]+ m/z: 723.5.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 23377-40-4, 3-(Hexadecyloxy)propan-1-ol.

Reference:
Patent; THE UNIVERSITY OF MANITOBA; OGUNSINA, Makanjuola; SAMADDER, Pranati; SCHWEIZER, Frank; ARTHUR, Gilbert; IDOWU, Temilolu; (119 pag.)WO2015/179983; (2015); A1;,
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Related Products of 5299-60-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.5299-60-5, name is Ethyl 6-hydroxyhexanoate, molecular formula is C8H16O3, molecular weight is 160.21, as common compound, the synthetic route is as follows.

To an oven-dried 3-necked 10 mL round-bottom flask under nitrogen was added l-cyclopentyl-3-(2-(4-hydroxyphenyl)-l,l-bis(3- (trifluoromethoxy)phenyl)ethyl)urea, prepared as described in Procedure 11, 6, 2 and 59, (50 mg, 0.1 mmol ), triphenylphosphine (34 mg, 0.1 mmol), ethyl 6- hydroxyhexanoate (17 mg, 0.1 mmol ) and dry THF (0.5 mL ). The reaction mixture was cooled in an ice-methanol bath and diethylazodicarboxylate ( 23 mg, 0.13 mmol ) was added via syringe. The reaction was allowed to warm to rt and stirred overnight. The reaction mixture was concentrated in vacuo and purified by ISCO silica gel chromatography using a gradient of 5-25% EtOAc / hexanes as eluent to yield ethyl 6-(4-(2-(3-cyclopentylureido)-2,2-bis(3-(trifluoromethoxy)phenyl)ethyl)phenoxy)hexanoate (Example 313) was isolated as a white solid (43 mg, 61% yield). HPLC: RT = 4.69 minutes ( Phenomenex Luna C18 5mu column 4.6 x 50 mm eluting with 10-90% aqueous methanol containing 0.1% phosphoric acid over a 4 minute gradient monitoring at 220 nni). LC/MS [M+H] 711.3 ( Phenomenex Luna C18 5mu column 4.6 x 30 mm eluting with 10-90% aqueous methanol containing 0.1% TFA over a 4 minute gradient monitoring at 220 nm). 1H NMR (400MHz , CDCl3) delta ppm 7.33 (t, J= 7.9 Hz, 2 H), 7.20 (d, J= 7.9 Hz, 2 H), 7.12 (d, J= 7.9 Hz, 2 H), 7.07 (s, 2 H), 6.62 (d, J= 8.8 Hz, 2 H), 6.56 (d, J= 8.8 Hz, 2 H), 4.10 (q, J= 7.1 Hz, 2 H), 3.86 t, J = 6.1Hz, 2 H), 3.68 (s, 1 H), 3.62 (t, J= 6.6Hz, 1 H), 2.30-2.27 (m, 2 H), 1.82-1.14 (m, 17 H), 1.23 (t, J= 7.1Hz, 3 H).

The chemical industry reduces the impact on the environment during synthesis 5299-60-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/62308; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1113-21-9, 3,7,11,15-Tetramethylhexadeca-1,6,10,14-tetraen-3-ol, 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, 1113-21-9, blongs to alcohols-buliding-blocks compound. Recommanded Product: 3,7,11,15-Tetramethylhexadeca-1,6,10,14-tetraen-3-ol

The 5E, 9E, 13E-geranyl geranyl acetone (1) can be prepared by reacting 6E-10E-geranyl linalool (23) with diketene (24) catalyzed by DMAP in ethyl ether to give the ester 25. The ester 25 in the Carroll rearrangement using Al(OiPr)3 at elevated temperature can afford the desired 5E, 9E, 13E-geranyl geranyl acetone (1). In another approach, the GGA (1) can be prepared by treating geranyl linalool (23) with the Meldrum’s acid 26 in the Carroll rearrangement using Al(OiPr)3 at 160 C. Similarly, the use of tert-butyl acetoacetate (27) with geranyl linalool (23) in the Carroll rearrangement can also give the desired 5E,9E,13E-geranyl geranyl acetone (1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1113-21-9, its application will become more common.

Reference:
Patent; COYOTE PHARMACEUTICALS, INC.; Look, Gary C.; US2015/133431; (2015); A1;,
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