Category: 6933-47-7

Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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: 6933-47-7

General procedure: A solution of (7: R1=cyclopentyloxy) (100mg, 363mumol) in dichloromethane (5 mL), cooled to 0C, was treated with oxalyl chloride (63.6 muL, 727 mumol), followed by a drop of N,N-dimethylformamide. The resultant mixture was stirred for 1h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in dichloromethane (5 mL) and then treated with a solution of methyl 4-aminobenzoate (8: R2=H, R=Me) (54.9mg, 363mumol) and di-isopropylethylamine (190muL, 1.09mmol) in dichloromethane (5mL). The reaction mixture was stirred for 12 h at room temperature and then partitioned between dichloromethane (20 mL) and aqueous 1M hydrochloric acid (20 mL). The phases were separated, and the organic phase was washed successively with water (2×20 mL), and brine (20 mL), dried over magnesium sulfate, filtered and then the solvent was removed in vacuo. The residue was purified by silica gel chromatography (12 g, 0-100 % ethyl acetate/isohexane) to afford methyl 4-[3,5-dichloro-4-(cyclopentyloxy)benzamido]benzoate (10: R1 = cyclopentyloxy, R2 = H, R =Me) (30mg, 20% yield). 1H NMR (400MHz, CDCl3) delta 8.06 (2H, d, J=8.8Hz,), 7.85 (1H, br s), 7.82 (2H, s), 7.71 (2H, d, J=8.8Hz), 5.07-5.03 (1H, m), 3.92 (3H, s), 2.10-1.90 (4H, m), 1.85-1.70 (2H, m), 1.70-1.60 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6933-47-7, its application will become more common.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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. Formula: C9H11NO2

Step 1: A stirred solution of compound 14 (1.0 g, 6.1 mmol) in acetic acid (10 mL) was treated dropwise with a solution of bromine (1.5 mL, 12 mmol) in acetic acid (5 mL). On completion of the addition, the resultant suspension was stirred at room temperature for 30 minutes, then water (50 mL) was added. A thick white ppt formed which was filtered, washed with water (3×50 mL) and air dried. The solid still contained water, so it was dissolved in dichloromethane and the solution was dried by passing through a hydrophobic frit. Evaporation of the solvent under reduced pressure afforded compound 15 as a cream solid (1.90 g). 1H NMR (400MHz, CDC13) delta 8.02 (s, 1H), 6.23 (br. s., 2H), 3.85 (s, 3H), 2.67 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6933-47-7, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MITCHELL, Glynn; MULHOLLAND, Nicholas, Phillip; BHONOAH, Yunas; (44 pag.)WO2016/198585; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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 Methyl 4-amino-2-methylbenzoate

General procedure: A solution of (7: R1=cyclopentyloxy) (100mg, 363mumol) in dichloromethane (5 mL), cooled to 0C, was treated with oxalyl chloride (63.6 muL, 727 mumol), followed by a drop of N,N-dimethylformamide. The resultant mixture was stirred for 1h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in dichloromethane (5 mL) and then treated with a solution of methyl 4-aminobenzoate (8: R2=H, R=Me) (54.9mg, 363mumol) and di-isopropylethylamine (190muL, 1.09mmol) in dichloromethane (5mL). The reaction mixture was stirred for 12 h at room temperature and then partitioned between dichloromethane (20 mL) and aqueous 1M hydrochloric acid (20 mL). The phases were separated, and the organic phase was washed successively with water (2×20 mL), and brine (20 mL), dried over magnesium sulfate, filtered and then the solvent was removed in vacuo. The residue was purified by silica gel chromatography (12 g, 0-100 % ethyl acetate/isohexane) to afford methyl 4-[3,5-dichloro-4-(cyclopentyloxy)benzamido]benzoate (10: R1 = cyclopentyloxy, R2 = H, R =Me) (30mg, 20% yield). 1H NMR (400MHz, CDCl3) delta 8.06 (2H, d, J=8.8Hz,), 7.85 (1H, br s), 7.82 (2H, s), 7.71 (2H, d, J=8.8Hz), 5.07-5.03 (1H, m), 3.92 (3H, s), 2.10-1.90 (4H, m), 1.85-1.70 (2H, m), 1.70-1.60 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6933-47-7, its application will become more common.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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. 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 6933-47-7

Step (viii): Methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate. A suspension of 217 3-chloro-4-ethoxy 5-isopropoxybenzoic acid (48: R2=iPr, R3=Et) (2.82g, 10.9mmol) and 145 methyl 4-amino-2-methylbenzoate (38: R1=Me) (2.16g, 13.1mmol) in 45 ethyl acetate (33mL) was treated with 46 triethylamine (4.56mL, 32.7mmol) followed by 44 T3P (50wt% in ethyl acetate) (17.34mL, 27.3mmol) and the mixture was heated at 60C for 4h and allowed to cool to room temperature for 16h. The reaction mixture was stirred vigorously with an aqueous solution of 218 sodium hydrogencarbonate (50mL) for 10min and separated. The aqueous layer was extracted with dichloromethane (3×100mL) and the combined organic phases were dried (magnesium sulfate), filtered concentrated in vacuo and the residue purified by silica gel chromatography (40g, 0:50:50 to 20:40:40 ethyl acetate:120 dichloromethane:isohexane) to produce 219 methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate as a beige solid (3.24g, 70% yield). 1H NMR (400MHz, CDCl3) delta 8.0 (1H, d, J=8.4Hz), 7.8 (1H, s), 7.59-7.50 (2H, m), 7.43-7.36 (2H, m), 4.69-4.73 (1H, m), 4.18 (2H, q, J=7.1Hz), 3.92 (3H, s), 2.6 (3H, s), 1.46-1.37 (9H, m). m/z 406 [M+H]+ (ES+), 404 [M-H]- (ES-).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 6933-47-7 as follows. HPLC of Formula: C9H11NO2

Intermediate 7.5.24-tert-Butoxycarbonylamino-2-methyl-benzoic acid methyl esterTo a stirred solution of intermediate 7.5.1 (1.5 g) in dioxane (15 ml) at 10 C. was added a solution of Boc anhydride (2.2 g) in dioxane (15 ml) dropwise and the reaction allowed to warm to rt. After 3 h, dimethylaminopyridine (catalytic amount) was added. After overnight stirring, the mixture was concentrated, and the residue was purified by flash chromatography (dichloromethan with ethanol gradient 0 to 4%) affording 0.69 g of the title compound.ESI mass spectrum: [M+H]+=266

According to the analysis of related databases, 6933-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/28938; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6933-47-7, 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. 6933-47-7 name is Methyl 4-amino-2-methylbenzoate, 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.

General procedure: Step (viii): Methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate. A suspension of 217 3-chloro-4-ethoxy 5-isopropoxybenzoic acid (48: R2=iPr, R3=Et) (2.82g, 10.9mmol) and 145 methyl 4-amino-2-methylbenzoate (38: R1=Me) (2.16g, 13.1mmol) in 45 ethyl acetate (33mL) was treated with 46 triethylamine (4.56mL, 32.7mmol) followed by 44 T3P (50wt% in ethyl acetate) (17.34mL, 27.3mmol) and the mixture was heated at 60C for 4h and allowed to cool to room temperature for 16h. The reaction mixture was stirred vigorously with an aqueous solution of 218 sodium hydrogencarbonate (50mL) for 10min and separated. The aqueous layer was extracted with dichloromethane (3¡Á100mL) and the combined organic phases were dried (magnesium sulfate), filtered concentrated in vacuo and the residue purified by silica gel chromatography (40g, 0:50:50 to 20:40:40 ethyl acetate:120 dichloromethane:isohexane) to produce 219 methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate as a beige solid (3.24g, 70% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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. 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: To a stirred solution of tert-butyl 2-formyl-6-azaspiro[3.4]octane-6-carboxylate (CAS: 203662-55-9) (225 mg, 1.0 mmol) and 2-(3-aminopheny])acetonitrile (CAS: 4623-249) (136 mg, 1.03 mmol) in MeOH (10 mL) at room temperature was added decaborane (43 mg, 0.35 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated. The residue was purified bysilica gel chromatography eluted with PE/EtOAc(3/1,v/v) to afford intermediate 119 (340 mg, 99% yield) as a yellow solid. Intermediate 178 was prepared via an analogous reaction protocol as described forthe preparation of intermediate 119, starting from the respective starting materials.

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6933-47-7,Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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 184-(3,5-Dichloro-4-ethoxybenzamido)-2-methylbenzoic acid (AAA-019)Step (i): Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3)1A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2- methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCI (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3 x 15 mL), dried over MgS04, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2- methylbenzoate (3) (267 mg, 56%): m/z 380 (M-H)” (ES”). 1H NMR (400 MHz, CDCI3) delta: 7.97 (1 H, s), 7.80 (3H, m), 7.54 (1 H, dd), 7.51 (1 H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; CORCORAN, Jonathan Patrick Thomas; KALINDJIAN, Sarkis Barret; BORTHWICK, Alan David; ADAMS, David Reginald; BROWN, Jane Theresa; TADDEI, David Michel Adrien; SHIERS, Jason, John; WO2011/27106; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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. 6933-47-7.

General procedure: Step (viii): Methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate. A suspension of 217 3-chloro-4-ethoxy 5-isopropoxybenzoic acid (48: R2=iPr, R3=Et) (2.82g, 10.9mmol) and 145 methyl 4-amino-2-methylbenzoate (38: R1=Me) (2.16g, 13.1mmol) in 45 ethyl acetate (33mL) was treated with 46 triethylamine (4.56mL, 32.7mmol) followed by 44 T3P (50wt% in ethyl acetate) (17.34mL, 27.3mmol) and the mixture was heated at 60C for 4h and allowed to cool to room temperature for 16h. The reaction mixture was stirred vigorously with an aqueous solution of 218 sodium hydrogencarbonate (50mL) for 10min and separated. The aqueous layer was extracted with dichloromethane (3¡Á100mL) and the combined organic phases were dried (magnesium sulfate), filtered concentrated in vacuo and the residue purified by silica gel chromatography (40g, 0:50:50 to 20:40:40 ethyl acetate:120 dichloromethane:isohexane) to produce 219 methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate as a beige solid (3.24g, 70% yield).

The synthetic route of Methyl 4-amino-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6933-47-7, name is Methyl 4-amino-2-methylbenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 6933-47-7

A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2-methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCl (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3*15 mL), dried over MgSO4, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3) (267 mg, 56%): m/z 380 (M-H)- (ES-). 1H NMR (400 MHz, CDCl3) delta: 7.97 (1H, s), 7.80 (3H, m), 7.54 (1H, dd), 7.51 (1H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics