Tag: M.W=100-200

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 5445-17-0 as follows. Computed Properties of C4H7BrO2

Example 13 Preparation of (Z)-3-(2-cyclopropylphenyl)-5-methyl-2-((E)-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazono)thiazolidin-4-one (Compound 127C) (Synthesis Method F) To (E)-N-(2-cyclopropylphenyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide (100 mg, 0.191 mmol) and sodium acetate (63.0 mg, 0.765 mmol) in EtOH (4 mL) was added methyl 2-bromopropanoate (0.026 mL, 0.230 mmol). The reaction was heated to 60 C. overnight. The reaction was then heated to 85 C. for 72 hours. The reaction mixture was diluted with DCM and washed with water. The aqueous layer was extracted with DCM. The organic layers were poured through a phase separator and concentrated. Purification by flash column chromatography provided the title compound as a white solid (32.5 mg, 0.056 mmol, 30%): mp 112-115 C.; 1H NMR (400 MHz, CDCl3) delta 8.58 (s, 1H), 8.32 (s, 1H), 8.22 (d, J=8.3 Hz, 2H), 7.87-7.75 (m, 4H), 7.43-7.32 (m, 4H), 7.26-7.24 (m, 2H), 4.23 (q, J=7.3 Hz, 1H), 1.85-1.78 (m, 4H), 0.90-0.78 (m, 2H), 0.78-0.69 (m, 1H), 0.65-0.55 (m, 1H); ESIMS m/z 578 (M+H).

According to the analysis of related databases, 5445-17-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Crouse, Gary D.; Sparks, Thomas C.; Dent, III, William H.; McLeod, CaSandra L.; Creemer, Lawrence C.; Demeter, David A.; Fritz, Amanda E.; Fischer, Lindsey G.; Baum, Erich W.; US2012/202687; (2012); A1;,
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Application of 135908-33-7, 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. 135908-33-7 name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 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 containing methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (298mg, 1.63 mmol), 4′-tert-butylbiphenyl-2-carboxylic acid (414 mg, 1.63 mmol), DMAP (227 mg, 1.86 mmol) and EDC HCl (470 mg, 2.45 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by chromatography (elution = 16:1 petrolueum ether/EtOAc) to afford methyl 4-(4′-fcrt-butylbiphenyl-2- ylcarboxamido)bicyclo[2.2.2]octane-l -carboxylate as an off-white solid (186 mg, yield: 27%). 1H NMR (400 MHz, CDCl3): delta 7.74 (IH, d, J= 6.4 Hz), 7.48-7.39 (4H, m), 7.35- 7.31 (3H, m), 4.77 (IH, s), 3.62 (3H, s), 1.79-1.75 (6H, m), 1.62-1.58 (6H, m), 1.36 (9H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2008/100423; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 36692-49-6, name is Methyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H10N2O2

Example 5 Synthesis of methyl 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-8-carboxylate A solution of methyl-1,2-phenylenediamine-4-benzoate (0.1 mol) and isatoic anhydride (0.1 mol) in acetic acid (75%) was heated at 120 C. for 2 hrs. The mixture was diluted with water and extracted with dichloromethane, washed with water and dried over Na2SO4. Methyl 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-8-carboxylate was isolated (92%) after removal of solvent under reduced pressure.

According to the analysis of related databases, 36692-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; US2010/228023; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 89-71-4,Some common heterocyclic compound, 89-71-4, name is Methyl 2-methylbenzoate, molecular formula is C9H10O2, 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.

2-Methyl-benzoic acid methyl ester (1.50 g 10 mmol), N-bromo-succinimide (1.96 g, 11 mmol) and 2,2′-azobis(2-methyl-propionitrile) (AIBN) (25 mg, 0.15 mmol) were dissolved in chloroform (3 ml). The solution was heated at reflux for 16 hours cooled and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a gradient of ethyl acetate/hexane (1-2 %) as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 2.05 g (89 %) of 2-bromomethyl-benzoic acid methyl ester as a solid. 1H-NMR (CDCl3): delta 7.97 (d, 1H, J = 7.6 Hz), 7.45-7.52 (m, 2H), 7.38 (dt, 1H, J = 1.2 Hz and J = 7.6 Hz), 4.96 (s, 2H), 3.95 (s, 1H). To a solution of 2-amino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (100 mg, 0.20 mmol) and pyridine (0.18 ml, 2.0 mmol) in acetonitrile (1 ml) at room temperature was added benzyl chloroformate (0.28 ml, 2.0 mmol) in 10 aliquots over 48 hours. The solution was then taken into ethyl acetate (30 ml), washed with 0.5 N hydrochloric acid (3×10 ml), saturated sodium bicarbonate (3 x 10 ml), brine (10 ml), dried (MgSO4) and filtered. The solvent was evaporated in vacuo. The resulting oil crystallized upon standing for 2 days. The precipitate was filtered off and washed with diethyl ether (3 x 1 ml) affording after drying in vacuo 59 mg (47 %) of 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester as a solid. 1H-NMR (CDCl3): delta 10.60 (s, 1H), 7.60-7.92 (m, 4H), 7.38 (m, 5H), 5.26 (s, 2H), 4.30-5.10 (m, 3H), 3.40-4.00 (m, 2H), 1.57 (m, 9H), 1.15 (m, 9H). To a solution of 1 N hydrochloric acid in ethyl acetate (1.0 ml) was added 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (52 mg, 0.08 mmol). The solution was stirred at room temperature for 48 hours. A precipitate was filtered off which afforded 42 mg (90 %) of 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride as a solid. 1H-NMR (DMSO-d6): delta 10.45 (s, 1H), 9.40 (s, 1H), 9.25 (s, 1H), 7.89 (m, 4H), 7.39 (m, 5H), 5.22 (s, 2H), 4.39 (d, 1H, J = 15 Hz), 4.28 (m, 1H), 3.95 (m, 2H), 3.79 (m, 1H), 3.20 (m, 1H), 2.70 (m, 1H), 1.48 (s, 9H). To a solution of the above 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride (42 mg, 0.072 mmol) in ethanol (0.5 ml) was added hydrazine (68 mul, 0.22 mmol). The solution was stirred at 80 C for 5 hours and at room temperature for 16 hours. The mixture was filtered and the filtrate evaporated in vacuo. The residue was extracted with dichloromethane (5 x 1 ml). The combined dichloromethane washes were evaporated in vacuo affording 20 mg (67 %) of 5-(S)-aminomethyl-2-benzyloxy-carbonylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil. 1H-NMR (CDCl3): delta 10.55 (bs, 1H), 7.37 (m, 5H), 5.23 (s, 2H), 3.92 (s, 2H), 2.60-3.10 (m, 3H), 1.53 (s, 9H). To a solution of the above 5-(S)-aminomethyl-2-benzyloxy-carbonylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (20 mg, 0.048 mmol) in acetonitrile (1 ml) at 0 C was added diisopropylethylamine (18 l, 0.15 mmol) and 2-bromomethyl-benzoic acid methyl (12 mg, 0.048 mmol). The solution was stirred at 0 C for 3 hours and at room temperature for 16 hours. Di-tert-butyl dicarbonate (21 mg, 0.096 mmol) was then added to the solution. The solution was then stirred at room temperature for 16 hours. The solution was taken into ethyl acetate (30 ml), washed with 0.5 N hydrochloric acid (3 x 10 ml), saturated sodium bicarbonate (3 x 10 ml) and brine (10 ml), dried (MgSO4) and filtered. The solvent was evaporated in vacuo. The solid residue was purified by silica gel chromatography using a 5 % mixture of ethyl acetate/hexane as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 10 mg (33 %) of 2-(benzyloxycarbonylamino)-5-(S)-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester as a solid. 1H-NMR (CDCl3): delta 10.59 (s, 1H), 7.81 (m, 1H), 7.52 (m, 1H), 7.39 (m, 7H), 5.25 (s, 1H), 4.22-5.00 (m, 4H), 4.40-4.80 (m, 2H), 2.80-3.10 (m, 2H), 1.55 (s, 9H), 1.25 (s, 9H). To a solution of the above 2-benzytoxycarbonylamino-5-(S)-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (9 mg, 0.014 mmol) in methanol (2 ml) was added 10 % Pd/C (4 mg). The mixture was stirred under hydrogen (1 atm.) for 3 hours and then filtered. The filtrate was evaporated in vacuo affordi…

The synthetic route of 89-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVO NORDISK A/S; Ontogen Corporation; EP1214324; (2006); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2216-92-4, name is N-Phenylglycine Ethyl Ester, molecular formula is C10H13NO2, 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. COA of Formula: C10H13NO2

tert-Butyl 4-(3-(2-ethoxy-2-oxoethyl)-3-phenylureido)piperidine-1-carboxylate. 4-Amino-1-N-Boc-piperidine (760 mg, 3.79 mmol) was dissolved in a mixture of dichloromethane (40 mL) and aqueous sodium bicarbonate (30 mL). A solution of 20% phosgene in toluene (10 mL, 18.9 mmol) was added to the mixture with vigorous stirring. Reaction stirred vigorously at room temperature for 40 minutes. Reaction layers were partitioned. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was dissolved in toluene (30 mL). N-Phenylglycine ethyl ester was added to the mixture. Reaction was heated at reflux for 15 hours. Mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). Mixture was washed successively with 1N hydrochloric acid (3×50 mL) and brine (30 mL). Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as pale yellow solid in 63% yield. 1H NMR (300 MHz, CDCl3): delta=7.47-7.26 (m, 5H), 4.30 (s, 1H), 4.16 (q, J=7.32, 2H), 3.88 (d, J=12.81, 2H), 3.81-3.69 (m, 1H), 2.89-2.70 (m, 2H), 1.83 (dd, J1=12.62, J2=3.11, 2H), 1.38 (s, 9H), 1.23 (t, J=7.14, 3H), 1.19-1.03 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2216-92-4, its application will become more common.

Reference:
Patent; Chaturvedula, Prasad V.; Mercer, Stephen E.; Fang, Haiquan; US2006/94707; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2208-05-1, name is 2-(Dimethylamino)ethyl benzoate, belongs to esters-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 2208-05-1, COA of Formula: C11H15NO2

EXAMPLE 39 N,N-Bis(2-(Benzoyloxy)ethyl)-N,N-dimethylammonium bromide Equimolar amounts of 2-bromoethyl benzoate (45.8 g) and 2-(N,N-dimethylamino)ethyl benzoate (38.5 g) were dissolved in 170 ml of acetonitrile and heated at reflux for 16 hours. The reaction mixture was then cooled and the resultant solid was collected, washed with ether, and dried to yield 62.4 g of the title compound, mp=169°-70° C. Anal. Calcd. for C20 H24 BrNO4: C, 56.88; H, 5.73; N, 3.32; Found: C, 56.49; H, 5.68; N, 3.38.

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-(Dimethylamino)ethyl benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eastman Kodak Company; US5194472; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 36692-49-6

To a solution of trans-3′-oxospiro [cyclohexane- [1,] [1′ (3’H)-ISOBENZOFURAN]-4-CARBOXYLIC ACID] (20 mg, 0.081 mmol) and methyl 3,4-diaminobenzoate (20 mg, 0.12 mmol) in pyridine (1 mL) was added 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (25 mg, 0.13 mmol). The mixture was stirred at room temperature for one hour under a nitrogen atmosphere, and then concentrated. After addition of saturated aqueous sodium bicarbonate to the residue, the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was washed with ethyl acetate-hexane, and dried to give the title compound (30.4 mg, 95 [%).]

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; WO2004/2986; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 4224-69-5, 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 4224-69-5 as follows.

Cyclopentylamine (5.79 mL, 58.7 mmol, 3.00 eq) and triethylamine (2.73 mL, 19.6 mL, 1.00 eq) were added to DCM (98 mL) and the reaction was cooled to 0 C. Methyl 2-(bromomethyl)acrylate (2.35 mL, 19.6 mmol, 1.00 eq) in DCM (48 mL) was added dropwise. Following addition the reaction was stirred for an additional 30 minutes at 0 C. Water was added and the layers separated. The aqueous layer was extracted with an additional portion of DCM and the combined organics were dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using 0- 60% DCM/MeOH/NH4OH (89: 10: 1) afforded 1.19 g (33%) of the title compound as a clear oil: 1H MR (400 MHz, DMSO-d6) 3 6.10 (s, 1H), 5.79 (s, 1H), 3.67 (s, 3H), 3.65 (d, J= 5.9 Hz, 1H), 3.56 (d, J= 15.1 Hz, 1H), 3.21 (d, J= 7.4 Hz, 1H), 2.98 (p, J= 6.2 Hz, 1H), 1.72-1.22 (m, 8H); ES-MS [M+l]+: 184.4.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; NISWENDER, Kevin; (90 pag.)WO2017/117556; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H11NO2

General procedure: To a solution of phenethylamine (200 mg, 1.65 mmol) and Et3N (0.64 mL, 4.95 mmol) in anhydrousTHF (2.5 mL) cooled with an ice bath, a solution of CS2 (0.12 mL, 1.98 mmol) was slowly dropped in.The reaction solution was stirred at room temperature for 0.5 h, after which AcCl (0.14 mL, 1.98 mmol)was dropped in at 0 C, and after 5 min the mixture was warmed to room temperature for 15-30 min.When the starting amine was finished, as verified by checking thin layer chromatography (T.L.C.),1MHCl (aq., 2 mL) was added to quench the reaction. The solution was extracted by EtOAc three times.All organic phases were combined and washed with brine, dried over Na2SO4, and finally filtered andconcentrated under reduced pressure. The residue was purified by column chromatography on silicagel (EtOAc/petroleum = 1/1) to provide phenethyl isothiocyanate (PEITC) (253 mg, 94%).

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Luo, Bingling; Wang, Jiankang; Li, Xiaobing; Lu, Wenhua; Yang, Jing; Hu, Yumin; Huang, Peng; Wen, Shijun; Molecules; vol. 22; 6; (2017);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 145576-28-9, 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 145576-28-9 as follows.

To a solution of dry dicyclohexylamine (0.777 mL, 3.90 mmol) in toluene (20 mL) in a round-bottom flask at 0 C. under Ar was added n-butyllithium (2.44 mL, 3.90 mmol) slowly. The reaction was stirred at 0 C. for 30 min. To this prepared lithium dicyclohexylamide solution was added ethyl 4-methylenecyclohexanecarboxylate (555 mg, 3.30 mmol) in toluene (1 mL) slowly over a period of 5 min. The reaction mixture was stirred at 0 C. for additional 30 min to generate the lithium enolate. In a 5 mL pear-shaped flask was placed di-p-bromobis(tri-tert-butylphosphino)dipalladium (I) (1.2 mg, 1.5 mumol) and the flask was capped with a rubber septum. Argon gas was flushed through the flask for 10 min. 1-Bromo-3-phenoxybenzene (747 mg, 3 mmol) in toluene (1 mL) was then added. The resulting solution was transferred via cannula into the round-bottom flask containing the 0 C. THF solution of the lithium enolate of the ethyl ester. Additional toluene (2×0.5 mL) was added to the pear-shaped flask, and this solution was also transferred into the round-bottom flask by cannula. The reaction mixture was allowed to warm to rt and stirred at rt for 3 days. The reaction was quenched with saturated aq. NH4Cl and diluted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by preparative HPLC (PHENOMENEX Axia 5mu C18 30×100 mm column; detection at 220 nm; flow rate=40 mL/min; continuous gradient from 30% B to 100% B over 10 min+2 min hold time at 100% B, where A=90:10:0.1 H2O:MeOH:TFA and B=90:10:0.1 MeOH:H2O:TFA) to afford the title compound (221 mg, 22% yield) as a colorless oil. LCMS, [M+H]+=337.1. 1H NMR (500 MHz, CDCl3) delta 7.38-7.33 (m, 2H), 7.33-7.27 (m, 1H), 7.19-7.10 (m, 3H), 7.04-6.99 (m, 2H), 6.89 (ddd, J=8.0, 2.4, 0.8 Hz, 1H), 4.68 (s, 2H), 4.17 (q, J=7.2 Hz, 2H), 2.61-2.53 (m, 2H), 2.36-2.21 (m, 4H), 1.88-1.79 (m, 2H), 1.22 (t, J=7.0 Hz, 3H).

According to the analysis of related databases, 145576-28-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Hao; Cheng, Peter T.W.; Chen, Sean; Tao, Shiwei; Wu, Shung C.; Negash, Lidet A.; US2014/275173; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics