Category: 1186-73-8

Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, 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 1186-73-8, Recommanded Product: Trimethyl methanetricarboxylate

N-benzyl-3-isopropyl-7-methoxy-6-(3-methoxypropoxy)tetralin-1-imine (1 g, 2.53 mmol) and trimethyl methanetricarboxylate (1.44 g, 7.6 mmol) were dissolved in diglyme (10 mL). The reaction mixture was stirred at 180 C in a microwave reactor for 30 minutes. Ethyl acetate (20 mL), followed by H2O (30 mL) were added to the reaction mixture. The separated organic layer was washed with H2O (2 x 20 mL), saturated aqueous brine solution (2 x 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by normal phase SiO2; chromatography (0 to 70 % EtO Ac/hexanes) to give methyl 1-benzyl-4-hydroxy-5-isopropyl-9-methoxy-8-(3-methoxypropoxy)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carboxylate as a yellow oil (560 mg, 42% yield, m/z: 522 [M+H] observed).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trimethyl methanetricarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Trimethyl methanetricarboxylate

Step 1: Methyl l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-9-tosyl-2,5,6,9-tetrahydro- 1H-pyrido[2′,3′:4,5]thiepino[3,2-f]indole-3-carboxylate o a stirring solution of Intermediate 9 (1.02 g, 2.75 mmol), (2,4-dimethoxyphenyl)methanamine (0.51 g, 0.45 mL, 3.03 mmol), triethylamine (0.83 g, 1.14 mL, 8.25 mmol) in CH2C12(6.0 mL) at 0 C was added a solution of TiCl4(1M in CH2C12,1.4 mL, 1.4 mmol) dropwise. After the addition, the mixture was brought to roomtemperature and stirred overnight. The reaction was quenched with satd. NaHC03solution (3 mL) and the mixture was diluted with CH2C12(12 mL). The CH2C12layer was separated and the aqueous layer was extracted with CH2C12(2 x 3 mL). The combined organics were evaporated to dryness followed by the addition of trimethyl methanetricarboxylate (1.05 g,5.5 mmol) and diphenyl ether (5.0 mL). The mixture was stirred at 230 C for 10 min, then cooled to room temperature and loaded directly onto a silica gel column. The product was chromato graphed (ethyl acetate in CH2C120-50 %) to furnish the title compound as a light brown solid (1.10 g, 62%). LC-MS: 647.2 [M+H]+, RT 1.57 min.

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1186-73-8,Some common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, molecular formula is C8H12O6, 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.

Step 5; methyl 9-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-8-methyl-2-oxo-2,5,6,8-tetrahydro-lH-indolo[6,5-h]quinoline-3- carboxylate The N-(2-(((tert-butyldimethylsilyl)oxy)methyl)- 1 -methyl-7,8-dihydro- 1H- benzo[f]indol-5(6H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (1.40 g, 2.84 mmol) and trimethyl methanetricarboxylate (0.95 g, 5.00 mmol) were mixed together in PI12O (7.0 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature) under a blanket of Argon. The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes followed by EtOAc/hexanes 25-60% gradient) to yield the product as a yellow foam (1.158 g, 63% 2 steps). XH NMR (500 MHz, CHCl3-i/) delta ppm 0.06 (s, 6 H) 0.90 (s, 9 H) 2.58 – 2.72 (m, 2 H) 2.89 (t, J=6.6 Hz, 2 H) 3.62 (s, 3 H) 3.78 (s, 3 H) 3.80 (s, 3 H) 3.97 (s, 3 H) 4.77 (s, 2 H) 5.37 (s, 2 H) 6.19 (s, 1 H) 6.42 (d, J=2.4 Hz, 1 H) 6.46 (dd, J=8.4, 2.4 Hz, 1 H) 7.14 (d, J=8.4 Hz, 1 H) 7.18 (s, 1 H) 7.63 (s, 1 H) 13.60 (s, 1 H). LC-MS 619.6 [M+H]+, RT 1.76 min.

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); 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. 1186-73-8, name is Trimethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

The intermediate N-(l-methyl-6,7-dihydrocyclohepta[fJindol-5(lH)-ylidene)prop-2-en- 1 -amine obtained above (ca. 8.46 mmol) and trimethyl methanetricarboxylate (2.75 g, 14.46 mmol) were mixed together in PI12O (17 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature). The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes, followed by EtOAc/hexanes 0-80% gradient) to provide the product as a yellow solid (2.15 g, 56% overall). ^ MR ^OO MHz, CHCl3-i/) 8 ppm 2.1 1 (ddd, J=14.1, 5.8, 2.0 Hz, 1 H) 3.51 (dd, J=14.1, 8.0 Hz, 1 H) 3.86 (s, 3 H) 4.01 (s, 3 H) 4.38 (dd, J=15.1, 5.9 Hz, 1 H) 4.53 (ddt, J=15.1, 4.6, 2.1 Hz, 1 H) 4.75 (dd, J=17.2, 1.1 Hz, 1 H) 5.05 (dd, J=10.4, 1.1 Hz, 1 H) 5.90 (dddd, J=17.2, 10.4, 5.9, 4.6 Hz, 1 H) 6.37 (ddd, J=9.8, 8.0, 5.8 Hz, 1 H) 6.53 (dd, J=3.2, 0.9 Hz, 1 H) 6.76 (dd, J=9.8, 2.0 Hz, 1 H) 7.20 (d, J=3.2 Hz, 1 H) 7.29 (s, 1 H) 7.85 (s, 1 H) 13.72 (br. s., 1 H). LC-MS 375.3 [M+H]+, 377.3 [M+H]+, RT 1.40 min.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1186-73-8.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1186-73-8, These common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, 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.

Step 1: Methyl 10-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-2,5,6,7-tetrahydro-lH-benzo[6,7]cyclohepta[l,2-b]pyridine-3-carboxylate The crude imine was combined with diphenyl ether (5 mL) and trimethylmethanetricarboxylate (1.07 g, 5.63 mmol). The reaction was stirred in a pre-heated 190 C bath for 1 hr. After cooling to room temperature, the mixture was purified by silica gel chromatography (5-50% EtOAc in hexanes). Trituration with acetone yielded the title compound (620 mg, 49%) as an off-white solid. 1H NMR (acetone- d6): delta 1.45 (m, 1H), 1.85-2.05 (m, 2H), 2.26 (m, 1H), 2.53 (dd, J = 13 Hz, 6 Hz, 1H), 2.96 (dd, J = 14 Hz, 6 Hz, 1H), 3.61 (s, 3H), 3.75 (s, 3H), 3.94 (s, 3H), 5.05 (d, J = 16 Hz, 1H), 5.28 (d, J = 16 Hz, 1H), 6.41 (m, 2H), 6.81 (d, J = 8.5 Hz, 1H), 7.27 (d, J = 8.5 Hz, 1H), 7.37 (m, 1H), 7.41 (dd, J = 8 Hz, 2.5 Hz, 1H), 13.83 (s, 1H)

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, molecular formula is C8H12O6, 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. SDS of cas: 1186-73-8

Embodiment 2; A. Synthesis of (3aS,4S,6aR)-1,3-dibenzyl-4-(omega,omega,omega-3-methoxycarbonyl butyl)-4H-1H-thiophene[3,4-d]iminazole-2,4(1H)- ketone; Put 300 ml methylbenzene and 60% sodium hydride 3.3 g (0.0825 mol) into the 500 ml four-neck flask with reflux condenser pipe, dropping pipette, stirrer and thermometric instrument which is protected by dry nitrogen; and then add 15.8 g (0.083 mol) methane tricarboxylic acid triethyl ester into the flask at the temperature of below 80 C. and protected for 2 h by heat preservation; add 33.3 g (0.075 mol) bromine sulfonium salts into the flask and then raise the temperature and control the temperature of the entire flask at 80 C. for a 15 h reaction; cool it to the normal temperature and use 5% sulfuric acid to adjust the pH to pH=3; separate the organic layer and extract the water layer by 100 ml methylbenzene for two times; use 40 ml 5% sodium bicarbonate water solution wash the organic layer for two times; dry the oil layer by anhydrous sodium sulfate, filtrate and reduce pressure to recycle faint yellow fluid, finally get the target object-0.2 g tri-ester dibenzyl biotin (95.3% of the theoretical value), and the HPLC measured content is 98.0% with no impurity 5 (hereinafter to be referred as dicarboxylic ester).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1186-73-8, its application will become more common.

Reference:
Patent; Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical Factory; US2012/65406; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1186-73-8,Some common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, molecular formula is C8H12O6, 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.

Put 300 ml methylbenzene and 60% sodium hydride 3.3g (0.0825 mol) into the 500 ml four-neck flask with reflux condenser pipe, dropping pipette, stirrer and thermometric instrument which is protected by dry nitrogen; and then add 15.8g(0.083 mol) methane tricarboxylic acid triethyl ester into the flask at the temperature of below 80C and protected for 2h by heat preservation; add 33.3g (0.075 mol) bromine sulfonium salts into the flask and then raise the temperature and control the temperature of the entire flask at 80C for a 15h reaction; cool it to the normal temperature and use 5% sulfuric acid to adjust the pH to pH=3; separate the organic layer and extract the water layer by 100 ml methylbenzene for two times; use 40 ml 5% sodium bicarbonate water solution wash the organic layer for two times; dry the oil layer by anhydrous sodium sulfate, filtrate and reduce pressure to recycle faint yellow fluid, finally get the target object-0.2g tri-ssterdibanzyl biotin (95.3% of the theoretical value), and the HPLC measured content is 98.0% with no impurity 5 (hereinafter to be referred as dicarboxylic ester).

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

Reference:
Patent; Zhejiang Medicine Co., Ltd.; EP2433942; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, 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 1186-73-8, Recommanded Product: Trimethyl methanetricarboxylate

Step 9: Methyl 10-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-2,5,6,8-tetrahydro- lH-benzo[6,7]oxocino[5,4-b]pyridine-3-carboxylate 9-Chloro-N-(2,4-dimethoxybenzyl)-4,5-dihydro-lH-benzo[c]oxocin-6(3H)-imine (ca. 0.3 g, 0.8 mmol) and trimethyl methanetricarboxylate (0.35 g, 1.8 mmol) were mixed in Ph20 (5 mL). The stirred mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after initial bubbling of MeOH was observed (occurs at approx. 160 C internal reaction temperature). The reaction mixture was cooled to room temperature, loaded directly on a silica column, eluted first with hexanes to separate Ph20 and then EtOAc/hexanes gradient (0-50%) to yield the title compound (41 mg, 11% over 2 steps) as a yellow foam. LC-MS: 484.1 [M-H]+, RT 1.45 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trimethyl methanetricarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, 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 1186-73-8, Safety of Trimethyl methanetricarboxylate

N-benzyl-3-isopropyl-7-methoxy-6-(3-methoxypropoxy)tetralin-1-imine (1 g, 2.53 mmol) and trimethyl methanetricarboxylate (1.44 g, 7.6 mmol) were dissolved in diglyme (10 mL). The reaction mixture was stirred at 180 C in a microwave reactor for 30 minutes. Ethyl acetate (20 mL), followed by H2O (30 mL) were added to the reaction mixture. The separated organic layer was washed with H2O (2 x 20 mL), saturated aqueous brine solution (2 x 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by normal phase SiO2; chromatography (0 to 70 % EtO Ac/hexanes) to give methyl 1-benzyl-4-hydroxy-5-isopropyl-9-methoxy-8-(3-methoxypropoxy)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carboxylate as a yellow oil (560 mg, 42% yield, m/z: 522 [M+H] observed).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trimethyl methanetricarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 1186-73-8

Step 1: Methyl l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-9-tosyl-2,5,6,9-tetrahydro- 1H-pyrido[2′,3′:4,5]thiepino[3,2-f]indole-3-carboxylate o a stirring solution of Intermediate 9 (1.02 g, 2.75 mmol), (2,4-dimethoxyphenyl)methanamine (0.51 g, 0.45 mL, 3.03 mmol), triethylamine (0.83 g, 1.14 mL, 8.25 mmol) in CH2C12(6.0 mL) at 0 C was added a solution of TiCl4(1M in CH2C12,1.4 mL, 1.4 mmol) dropwise. After the addition, the mixture was brought to roomtemperature and stirred overnight. The reaction was quenched with satd. NaHC03solution (3 mL) and the mixture was diluted with CH2C12(12 mL). The CH2C12layer was separated and the aqueous layer was extracted with CH2C12(2 x 3 mL). The combined organics were evaporated to dryness followed by the addition of trimethyl methanetricarboxylate (1.05 g,5.5 mmol) and diphenyl ether (5.0 mL). The mixture was stirred at 230 C for 10 min, then cooled to room temperature and loaded directly onto a silica gel column. The product was chromato graphed (ethyl acetate in CH2C120-50 %) to furnish the title compound as a light brown solid (1.10 g, 62%). LC-MS: 647.2 [M+H]+, RT 1.57 min.

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics