Author: tianli

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;,
Alcohol – Wikipedia,
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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;,
Alcohol – Wikipedia,
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Reference of 431-38-9 ,Some common heterocyclic compound, 431-38-9, molecular formula is C3H6F3NO, 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 solution of 150 mg intermediate 6-[4-(difluoromethoxy)phenyl]-2-(3-fluorophenyl)-3-oxo-2,3- dihydropyridazine-4-carboxylic acid, 92.6 mg amino-1 ,1 ,1 -trifluoro-2-propanol, 273 mg HATU, 0.19 mL ethyldiisopropylamine and 2.2 mg 4-dimethylaminopyridine in 3 mL of DMF was stirred at room temperature for 48 hours. Then the reaction mixture was filtered and subjected to RP-HPLC (Instrument: Waters Autopurification MS SingleQuad; Colum: Waters XBrigde C18 5mu 100x30mm; eluent A: water + 0.2 vol % aqueous ammonia (32%), eluent B: acetonitrile; gradient: 0-5.5 min 5-100% B; flow 70 mL/min; temperature: 25 C; DAD scan: 210-400 nm) to yield 62 mg 6-[4-(difluoromethoxy)phenyl]-2-(3-fluorophenyl)-3-oxo-N-(3,3,3- trifluoro-2-hydroxypropyl)-2,3-dihydropyridazine-4-carboxamide. 1H NMR (400 MHz, DMSO-d6) delta ppm = 3.48 (br dd, 1 H), 3.69 – 3.81 (m, 1 H), 4.22 (br s, 1 H), 6.66 (br d, 1 H), 7.27 – 7.43 (m, 4 H), 7.55 (br d, 1 H), 7.58 – 7.66 (m, 2 H), 7.99 – 8.08 (m, 2 H), 8.67 (s, 1 H), 8.62 – 8.74 (m, 1 H), 9.66 (br s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,431-38-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); SCHMEES, Norbert; GUTCHER, Ilona; IRLBACHER, Horst; BADER, Benjamin; ZHAO, Na; PLATTEN, Michael; (437 pag.)WO2017/202816; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 23147-58-2, Glycerol aldehyde dimer, 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, Formula: C4H8O4, blongs to alcohols-buliding-blocks compound. Formula: C4H8O4

Step 2: (S)-2-Amino-N-[(S)-1-(6-bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl]-butyramide was dissolved in MeOH (2 mL) and15 glycolaldehyde dimer (10.9 mg, 90.5 ).IDOl, Eq: 0.55), acetic acid (9.5 )lL, 165 ).IDOl, Eq: 1.0) andsodium cyanoborohydride (15.5 mg, 247 ).IDOl, Eq: 1.5) were successively added. The mixturewas stirred at RT overnight. The mixture was diluted with 1 N HCl, 1 N NaOH added to adjust thepH to ca. 11. The mixture was extracted with EtOAc, the extracts washed with brine, dried overNa2S04, concentrated and the resulting material purified by flash chromatography to afford the20 title compound which was lyophilized from MeCN/H20 (55 mg, 60 %). MS m/z 556.0 (MH+

The synthetic route of 23147-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xiaochun; LOU, Yan; MICHOUD, Christophe; MISCHKE, Steven Gregory; REMISZEWSKI, Stacy; RUPERT, Kenneth Carey; WO2014/9495; (2014); A1;,
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Synthetic Route of 261723-32-4 ,Some common heterocyclic compound, 261723-32-4, molecular formula is C7H6BrFO, 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 (3-bromo-2-fluoro-phenyl)methanol (2.750 g, 13.413 mmol) in dichloromethane (50 mL) was added manganese dioxide (9.32 g, 107.31 mmol) and the resulting mixture was stirred at 45C overnight. Once complete, the reaction was filtered through diatomaceous earth and washed with dichloromethane to obtain 3-bromo-2-fluoro-benzaldehyde as a white solid (2.24 g, 83%). lU NMR (400 MHz, DMSO-i ) delta 10.19 (dt, = 1.3, 0.7 Hz, 1H), 8.05 (tdd, = 6.8, 3.1, 1.5 Hz, 1H), 7.85 (ddt, = 7.9, 6.4, 1.5 Hz, 1H), 7.37 (tdt, = 7.8, 1.6, 0.8 Hz, 1H).

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. 261723-32-4, (3-Bromo-2-fluorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; YU, Jiang; WU, Guosheng; YUEN, Po-Wai; VILLEMURE, Elisia; SCHWARZ, Jacob; LY, Cuong; SELLERS, Benjamin; VOLGRAF, Matthew; WO2015/52226; (2015); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 10488-69-4, Ethyl 4-chloro-3-hydroxybutanoate, 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, 10488-69-4, blongs to alcohols-buliding-blocks compound. Recommanded Product: Ethyl 4-chloro-3-hydroxybutanoate

S(-)-4-chloro-3-hydroxybutyric acid ethyl ester (100g) andL-2-Aminobutyramide is the starting material (61.3g),With chloroform as solvent,Add acid agent potassium carbonate (81.3g),While stirring at reflux, the reaction was incubated for 4 hours.After confirming that the reaction of raw materials is completed, the reaction solution is washed twice with 150 mL of dichloromethane, and the organic phase is dried.It is reduced to no fractions and purified by column to give product intermediate I, namely (S)-2-((S)-4-hydroxy-2-oxopyrrolidin-1-yl)butyrylAmine, 96.3 g, purity 98.4percent, yield 86.3percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10488-69-4, its application will become more common.

Reference:
Patent; Emeishan Hongsheng Pharmaceutical Co., Ltd.; Lu Chengxian; Tian Jianhong; Tian Yangyang; Che Shangze; Tian Jinyuan; (10 pag.)CN107513032; (2017); A;,
Alcohol – Wikipedia,
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