294190-18-4 Archives - Esters-buliding-blocks

Sources of common compounds: Methyl 3-amino-5-chloro-2-methylbenzoate

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.

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. 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 294190-18-4

[01713] Step 1 : Synthesis of methyl 5-chloro-3-(isobutyl amino)-2-methylbenzoate[01714] To a stirred solution of methyl 3-amino-5-chloro-2-methyl benzoate (5.0 g, 25 mmol) and isobutyraldehyde (4.5 g, 62 mmol) in methanol (50 mL), acetic acid (3.0 g, 50 mmol) was added and reaction stirred at room temperature for 2 h. Then sodium cyanoborohydride (3.94 g, 62 mmol) was added at 0C and reaction stirred overnight at room temperature. On completion, the solvent was removed under reduced pressure and the crude material was purified by column chromatography to afford the title compound (6.0 g, 94 %).

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Introduction of a new synthetic route about C9H10ClNO2

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. 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 294190-18-4

[0968] tert-Buty 4-{[5-chloro-3-(methoxycarbonyl)-2-methylphenyI]amino}piperidine-l- carboxylate[0969] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1.40 g, 7.04 mmol) in CH2CI2 (30 mL) and AcOH (2.50 g, 42.2 mmol) was added N-Boc piperidinone (1.96 g, 9.85 mmol) and sodium triacetoxyborohydride (4.40 g, 21 .1 mmol). The reaction mixture was stirred at 23 C for 1 8 hours and then saturated NaHC03 was added and the mixture was separated. The aqueous layer was extracted with CH2CI2 (3 x 20 mL) and the combined organic layers were concentrated in vacuo. The residue was purified by silica gel columnchromatography (Si02 heptane/ethylacetate=10/l to 1 /1 ) to give the titled compound as oil (2.40 g, 89% yield). -NMR (400 MHz, CDC13) 5ppm; 7.09 (s, 1 H), 6.69 (s, 1 H), 4.05(m, 2H), 3.88 (s, 3H), 3.63 (m, 1 H), 3.42 (m, 1 H), 2.97 (m, 2H), 2.23 (s, 3H), 2.05 (m, 2H), 1 .45 (s, 9H), 1 .27 (m, 2H).

According to the analysis of related databases, 294190-18-4, the application of this compound in the production field has become more and more popular.

Research on new synthetic routes about C9H10ClNO2

[01341 ] Step 1 : Synthesis of methyl -chloro-3-(cycloheptylamino)-2-methylbenzoate[01 342] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1 g, 5.02 mmol) and cycloheptanone (2.81 g, 25 mmol) in methanol (10 mL), acetic acid (0.3 g, 5.02 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.65 g, 10.05 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford 5- chloro-3-(cycloheptylamino)-2-methylbenzoate (0.8 g, 56.2 %).

A new synthetic route of 294190-18-4

Synthetic Route of 294190-18-4,Some common heterocyclic compound, 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, molecular formula is C9H10ClNO2, 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.

[01289] Step 1 : Synthesis of methyl 3-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-5-chloro- 2-methylbenzoate[01290] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1 g, 4.6 mmol) and tert-butyl (2-oxoethyl)carbamate ( 1 .4 g, 8.8 mmol) in methanol ( 10 mL), acetic acid (0.027 g, 4.6 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.352 g, 4.68 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford the desired product (0.62 g, 38 %).

The synthetic route of 294190-18-4 has been constantly updated, and we look forward to future research findings.

New learning discoveries about 294190-18-4

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, Methyl 3-amino-5-chloro-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 294190-18-4, The chemical industry reduces the impact on the environment during synthesis 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, I believe this compound will play a more active role in future production and life.

Step 1 : Synthesis of methyl 3-(((trans)-4-((tert-butoxycarbonyl) amino) cyclohexyl) amino)-5-chloro-2-methylbenzoate: [0910] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate (100 g, 502 mmol) and tert-butyl (4-oxocyclohexyl) carbamate (160.5 g, 753 mmol) in dichloroethane (1 L), acetic acid (180.9 g, 3015 mmol) was added and the reaction was stirred at rt for 30 min. Then sodium triacetoxyborohydride (319.5 g, 1507 mmol) was added at 0 C and the reaction was stirred at rt for 16 h. The progress of the reaction was monitored by TLC. Upon completion; the reaction was quenched with aqueous sodium bicarbonate, the organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography (100-200 mesh size) eluting with 2, 4, 6 & 8% ethyl acetate in hexane to remove maximum cis isomer. This afforded 120 g of mixture of cis and trans isomers (40:60 by HPLC). The trans isomer was purified by repetitive recrystazlisation with ethyl acetate: hexane (1 :2) to afford 65 g of pure trans isomer (65 g, 33%).

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10049; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Simple exploration of 294190-18-4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-5-chloro-2-methylbenzoate, its application will become more common.

Reference of 294190-18-4,Some common heterocyclic compound, 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, molecular formula is C9H10ClNO2, 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.

[01783] Step 1 : Synthesis of methyl 3-(((l r,4r)-4-((tert- butoxycarbonyl)amino)cyclohexyl)amino)-5-chloro-2-methylbenzoate[01 784] To a stirred solution of methyl 3-amino-5-chloro-2-methyl benzoate (5.0 g, 25 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (6.95 g, 32.6 mmol) in 25 ml of dichloroethane, was added acetic acid (9.0 mL, 450.75 mmol) at room temperature. The reaction mixture was cooled and sodium triacetoxyborohydride (22.8 g, 108 mmol) was added and the mixture stirred at room temperature overnight. The mixture was neutralized with sat. NaHC03 and extracted with DCM. The combined organic phases were dried over a2S04, concentrated under reduced pressure and the product isomers separated by silica gel (100-200) column chromatography to give the less polar as m-isomer, methyl 3-((( l s,4s)-4-((tert- butoxycarbonyl)amino)cyclohexyl)amino)-5-chloro-2-methylbenzoate (5.2 g, 52%) and the more polar title compound /rara-isomer, methyl 3-(((l r,4r)-4-((tert- butoxycarbonyl)amino)cyclohexyl)amino)-5-chloro-2-methylbenzoate (3.5 g, 35%).