863127-76-8

Basic information

• Product Name: (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide
• Synonyms: (E)-N-(2-CHLORO-6-METHYLPHENYL)-3-ETHOXYACRYLAMIDE;(2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxy-2-propenamide;2-PropenaMide,N-(2-chloro-6-Methylphenyl)-3-ethoxy-, (2E)-;Dasatinib Impurity 14
• CAS NO: 863127-76-8
• Molecular Formula: C₁₂H₁₄ClNO₂
• Molecular Weight: 239.7
• EINECS: 1312995-182-4
• Mol File: 863127-76-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 386.5 °C at 760 mmHg
• Flash Point: 187.6 °C
• Appearance: /
• Density: 1.197
• Refractive Index: 1.572
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.57±0.70(Predicted)
• CAS DataBase Reference: (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide(863127-76-8)
• EPA Substance Registry System: (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide(863127-76-8)

Safety Data

• Hazardous Substances Data: 863127-76-8(Hazardous Substances Data)

Usage

Uses

(2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxy-2-propenamide is a reagent used for the preparation of potent and selective anti-tumor drug Dasatinib.

InChI:InChI=1/C12H14ClNO2/c1-3-16-8-7-11(15)14-12-9(2)5-4-6-10(12)13/h4-8H,3H2,1-2H3,(H,14,15)/b8-7+

Synthetic route

(2E)-3-ethoxyprop-2-enoyl chloride (6191-99-7, 99471-66-6) + 2-chloro-6-methylaniline (87-63-8) → (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide (863127-76-8)

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 3h;	78.3%
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h;	73.6%
With pyridine In tetrahydrofuran at 0 - 20℃;	73.6%
With pyridine In tetrahydrofuran at 10 - 30℃; for 4h;	300 g

3-ethoxyacryloyl chloride (6191-99-7) + 2-chloro-6-methylaniline (87-63-8) → (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide (863127-76-8)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃;
With pyridine In tetrahydrofuran at 20℃;

ethyl 3-ethoxyacrylate (1001-26-9) → (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide (863127-76-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; water / 2 h / Reflux 2: thionyl chloride / 2 h / Reflux 3: pyridine / tetrahydrofuran / 20 °C View Scheme

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide (863127-76-8) + thiourea (17356-08-0) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With iodine(I) bromide; 1-n-butyl-3-methylimidazolim bromide In tetrahydrofuran at 40℃; Stage #2: thiourea In tetrahydrofuran for 1.5h; Temperature; Concentration; Solvent; Reagent/catalyst;	98.8%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane; water at -10 - 22℃; for 3h; Stage #2: thiourea In 1,4-dioxane; water at 100℃; for 2h; Stage #3: With ammonia In 1,4-dioxane; water at 20 - 22℃;	90%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane at -10 - 22℃; for 3h; Stage #2: thiourea In 1,4-dioxane at 100℃; for 2h; Stage #3: With ammonium hydroxide In 1,4-dioxane; water at 20 - 22℃;	90%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane; water at 25 - 30℃; for 3h; Stage #2: thiourea In 1,4-dioxane; water at 25 - 70℃; for 2h;	213 g

Upstream product

• 6191-99-7 (2E)-3-ethoxyprop-2-enoyl chloride 
• 87-63-8 2-chloro-6-methylaniline 
• 1001-26-9 ethyl 3-ethoxyacrylate 
• 6191-99-7 3-ethoxyacryloyl chloride 

Downstream Products

• 302964-24-5 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide 
• 1035343-44-2 C₁₅H₁₂Cl₂N₆OS 
• 1035343-45-3 C₂₁H₂₅ClN₈O₂S 
• 1035343-47-5 C₂₀H₂₃ClN₈OS 
• 1035343-70-4 C₂₂H₂₇ClN₈O₂S 
• 1258411-33-4 C₂₂H₂₉ClN₈OS 
• 1258411-04-9 C₂₅H₃₂ClN₉O₂S 
• 1258411-05-0 C₂₅H₂₆ClN₉OS 
• 1035343-57-7 C₂₁H₂₄ClN₇O₂S 
• 1258411-07-2 C₁₉H₂₁ClN₈OS 
• 1258411-08-3 C₂₂H₂₄ClN₉OS 
• 1258411-09-4 C₂₄H₂₄ClN₉OS 
• 1258411-10-7 C₂₃H₂₃ClN₁₀OS 
• 1258411-11-8 C₂₅H₂₅ClN₈OS 

Relevant articles and documents

CRYSTALLINE FORMS OF N-(2-CHLORO-6-METHY]PHENVN-2-[F6-[4-(2-HVDROXVETHVL)-L- PIPERAZINVIL-2-METHVL-4-PVRIMIDINVLLAMINOL-5-THIAZOLECARBOXAMIDE AND THEIR PROCESS THEREOF

The present invention relates to crystalline 1,2-Propanediol solvate of N-(2-chloro-6- methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-l-piperazinyl]-2-methyl-4-pyrimidinyl]ainino]-5- thiazolecarboxamide compound of formula- lb, its process for the preparation and its use in the preparation of anhydrous crystalline form (N-6) and monohydrate of N-(2-chloro-6- methy lphenyl)-2- [ [6- [4-(2 -hydroxy ethyl)- 1 -piperazinyl] -2-methyl-4-pyrimidinyl]amino] -5 - thiazolecarboxamide. [formula] 1,2-Propanediol solvate Formula- lb

TRIAZINE DERIVATIVES AND THEIR THERAPEUTICAL APPLICATIONS

The present invention comprises inter alia compounds as shown in formula (I) or a pharmaceutically acceptable salt thereof.

TRIAZINE DERIVATIVES AND THEIR THERAPEUTICAL APPLICATIONS

The invention provides for Triazine derivatives and their use to modulate protein kinase activity in a variety of conditions and diseases.