302964-24-5

Basic information

• Product Name: 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
• Synonyms: Dasatinib IMpurity 2;2-AMino-N-(2-chloro-6-Methylphenyl)thiazole-5-carboxiMide);2-Amino-5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazole, 2-Amino-5-[(6-chloro-o-tolyl)carbamoyl]-1,3-thiazole;2-AMino-N-(2-chloro-6-Methylphenyl)-5-thiazolecarboxaMide;5-ThiazolecarboxaMide,2-aMino-N-(2-chloro-6-Methylphenyl);Dasatinib Int N-2;2-AMino-N-(2-chloro-6-Meth;2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
• CAS NO: 302964-24-5
• Molecular Formula: C₁₁H₁₀ClN₃OS
• Molecular Weight: 267.73
• EINECS: 1806241-263-5
• Product Categories: Dasatinib;API intermediates
• Mol File: 302964-24-5.mol
• Article Data: 32

Chemical Properties

• Melting Point: 208.0 to 212.0 °C
• Boiling Point: 362 °C at 760 mmHg
• Flash Point: 172.7 °C
• Appearance: /
• Density: 1.474 g/cm³
• Vapor Pressure: 1.99E-05mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 11.09±0.70(Predicted)
• CAS DataBase Reference: 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide(302964-24-5)
• EPA Substance Registry System: 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide(302964-24-5)

Safety Data

• Hazardous Substances Data: 302964-24-5(Hazardous Substances Data)

Usage

General Description

2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, also known as TMC-120, is a chemical compound that belongs to the class of thiazole derivatives. It is a yellow solid substance with a molecular formula of C11H10ClN3OS and a molecular weight of 265.7 g/mol. TMC-120 is primarily used in the pharmaceutical industry for its potential medicinal properties, including its antifungal and antimicrobial activities. It is also being investigated for its potential use in the treatment of various diseases and infections. The compound is typically synthesized through chemical reactions and processes in a laboratory setting.

InChI:InChI=1/C15H17N3O/c1-9-6-10(2)14(11(3)7-9)18-15(19)12-4-5-17-8-13(12)16/h4-8H,16H2,1-3H3,(H,18,19)

Synthetic route

N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide + thiourea (17356-08-0) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide With 1-butyl-3-methylimidazolium Tetrafluoroborate; copper(I) bromide In tetrahydrofuran for 0.5h; Stage #2: thiourea In tetrahydrofuran at 40℃; for 1.5h; Temperature; Solvent; Reagent/catalyst;	98.9%
Stage #1: N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide With N-Bromosuccinimide In 1,4-dioxane; water at 0 - 10℃; Stage #2: thiourea In 1,4-dioxane; water at 20 - 80℃;	85 g
With N-Bromosuccinimide at -10 - 80℃;

(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

C10H9BrClNO2 + thiourea (17356-08-0) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
for 0.0611111h; Microwave irradiation;	97.23%
at 20℃; for 1h;	95.94%
In water at 20℃; for 2h; Solvent;	95.94%

C10H10ClNO2 (1044209-25-7) + thiourea (17356-08-0) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
With copper(ll) bromide In tetrahydrofuran; water at 35 - 40℃; for 0.5h; Reagent/catalyst; Solvent;	96.13%

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 N-Bromosuccinimide In 1,4-dioxane; water at -10 - 22℃; for 3h; Stage #2: thiourea In 1,4-dioxane; water at 80℃; for 2h;	94.9%

3-oxo-propionic acid ethyl ester (34780-29-5) + thiourea (17356-08-0) + 2-chloro-6-methylaniline (87-63-8) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 0.75h; Reflux; Stage #3: thiourea Solvent; Further stages;	92.31%
Stage #1: 3-oxo-propionic acid ethyl ester; 2-chloro-6-methylaniline With sodium methylate In tetrahydrofuran for 0.75h; Reflux; Stage #2: With copper(ll) bromide In tetrahydrofuran for 1h; Reflux; Stage #3: thiourea In tetrahydrofuran at 20 - 25℃; for 0.25h; Reagent/catalyst;	90.94%

[5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester (302964-06-3) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
With trifluoroacetic acid at 25 - 30℃; for 2h;	89%
With trifluoroacetic acid In dichloromethane at -5 - 20℃; for 10.5h;	85%
With trifluoroacetic acid at 25 - 30℃; Reagent/catalyst; Temperature;	78%

N-(2-chloro-6-methylphenyl)-2-(tritylamino)thiazole-5-carboxamide → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
With formic acid In ethanol Heating / reflux;	70%

2-chloro-6-methylaniline (87-63-8) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: i-Pr2NEt / tetrahydrofuran 2: TFA / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran 2: N-Bromosuccinimide / -10 - 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium methylate / tetrahydrofuran / 0.17 h / 20 °C 1.2: 1 h / Reflux 1.3: 2 h / Reflux 2.1: water / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium methylate / tetrahydrofuran / 10 h / 20 °C 1.2: 1 h / Reflux 2.1: copper(ll) bromide / tetrahydrofuran; water / 0.5 h / 35 - 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium methylate / tetrahydrofuran / 1 h / Reflux 1.2: 2 h / Reflux 2.1: 0.06 h / Microwave irradiation View Scheme

2-chloro-N-(2-chloro-6-methyl-phenyl)-3,3-dimethoxy-propionamide + thiourea (17356-08-0) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: 2-chloro-N-(2-chloro-6-methyl-phenyl)-3,3-dimethoxy-propionamide; thiourea With hydrogenchloride; acetic acid at 50 - 65℃; for 11h; Industry scale; Stage #2: With sodium methylate In methanol pH=8 - 9; Industry scale;

C12H13BrClNO2 + thiourea (17356-08-0) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: C12H13BrClNO2; thiourea In 1,4-dioxane; water at 80℃; for 2h; Stage #2: With ammonium hydroxide In 1,4-dioxane; water at 20 - 22℃;	5.3 g

C11H11BrClN3OS → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
In dichloromethane at 20℃;

N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / 1,4-dioxane; water 2: dichloromethane / 20 °C View Scheme

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

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; water / 1,4-dioxane / 3 h / -10 - 22 °C 2: 1,4-dioxane; water / 2 h / 80 °C View Scheme

C12H15BrClNO3 (1416737-47-7) + thiourea (17356-08-0) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
In 1,4-dioxane; water at 80℃; for 2h;	2.4 g

2-amino-thiazole-5-carboxylic acid ethyl ester (32955-21-8) + 2-chloro-6-methylaniline (87-63-8) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: 2-chloro-6-methylaniline With ethyl bromide; iodine; magnesium In tetrahydrofuran at 0 - 20℃; Stage #2: 2-amino-thiazole-5-carboxylic acid ethyl ester In tetrahydrofuran	17.0 g

N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide + N-tritylthiourea (76758-01-5) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide With N-Bromosuccinimide In 1,4-dioxane; water at 0 - 10℃; Stage #2: N-tritylthiourea In 1,4-dioxane; water at 20 - 80℃;	85 g

3-ethoxyacryloyl chloride (6191-99-7) + thiourea (17356-08-0) + 2-chloro-6-methylaniline (87-63-8) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: 3-ethoxyacryloyl chloride; 2-chloro-6-methylaniline Stage #2: thiourea With N-Bromosuccinimide

2,4-dichloro-2-methylpyrimidine (1780-26-3) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (302964-08-5)

Conditions	Yield
With potassium hydride In tetrahydrofuran at -25 - -10℃; for 4h; Reagent/catalyst; Temperature;	98.7%
Stage #1: 2,4-dichloro-2-methylpyrimidine; 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide In tetrahydrofuran at 5 - 20℃; for 0.75h; Stage #2: With sodium t-butanolate In tetrahydrofuran at 5 - 10℃; for 2.25h;	97%
Stage #1: 2,4-dichloro-2-methylpyrimidine; 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide With sodium t-butanolate In tetrahydrofuran at 10 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0 - 5℃; for 2h; pH=2 - 3; Temperature; Reagent/catalyst;	94%

C10H18N2O4 + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → C20H24ClN5O4S

Conditions	Yield
Stage #1: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide With trimethylaluminum In hexane; dichloromethane at 20℃; for 2h; Stage #2: C10H18N2O4 In hexane; dichloromethane at 60℃; for 5h; Solvent; Reagent/catalyst;	98%

1-(2-hydroxyethyl)piperazine (103-76-4) + 2,4-dichloro-2-methylpyrimidine (1780-26-3) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → dasatanib (302962-49-8)

Conditions	Yield
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine With potassium phosphate; 1-butyl-3-methylimidazolium aminoethanic acid salt at 80℃; for 1.5h; Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide at 20 - 80℃; for 2h; Reagent/catalyst;	92.27%
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine With potassium phosphate; 1-butyl-3-methylimidazolium aminoethanic acid salt In N,N-dimethyl acetamide at 80℃; for 2h; Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide In N,N-dimethyl acetamide at 80℃; for 3h; Solvent;	89.31%
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine With copper(l) iodide; dimethylaminoacetic acid; O4P(3-)*O4P(3-)*3K(1+) In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide at 120℃; for 6h; Inert atmosphere;	88.41%

Monomethyl terephthalate (1679-64-7) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → C20H16ClN3O4S

Conditions	Yield
Stage #1: Monomethyl terephthalate With triethylamine; HATU In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide In tetrahydrofuran at 20℃;	85%

2,4-dichloro-2-methylpyrimidine (1780-26-3) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → (2-(6-chloro-2-methylpyrimidine-4-ylamino)-N-(2-chloro-6-methylpbenyl)thiazole-5-carboxamide)

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at 10 - 30℃; Inert atmosphere; Large scale;	83.5%

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol (127116-19-2) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → dasatanib (302962-49-8)

Conditions	Yield
In 1,4-dioxane at 75℃; for 3h; Concentration;	83.2%
With potassium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl at 100 - 110℃; for 20h;

chloroacetyl chloride (79-04-9) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → N-(2-chloro-6-methylphenyl)-2-(2-chloroacetamido)-5-thiazolecarboxamide (1323138-80-2)

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 0 - 60℃; for 3.08h;	80.6%
With triethylamine In dichloromethane at 0 - 20℃;	73.6%

p-(chloromethyl)benzoyl chloride (876-08-4) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → N-(2-chloro-6-methylphenyl)-2-[4-(chloromethyl)benzamido]thiazole-5-carboxamide

Conditions	Yield
Stage #1: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide With triethylamine In tetrahydrofuran for 0.25h; Cooling; Stage #2: p-(chloromethyl)benzoyl chloride In tetrahydrofuran for 3h;	76.44%

2-((pyridin-4-ylmethyl)amino)nicotinic acid (854382-06-2) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → N-(2-chloro-6-methylphenyl)-2-(2-((pyridin-4-ylmethyl)amino)nicotinamido)thiazole-5-carboxamide

Conditions	Yield
Stage #1: 2-((pyridin-4-ylmethyl)amino)nicotinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide In N,N-dimethyl-formamide at 20℃; for 16h; Cooling with ice;	74.1%

6-bromohexanoic acid (4224-70-8) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → C17H20ClN3O3S

Conditions	Yield
With triethylamine In tetrahydrofuran at 60℃;	62%

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → 2-bromo-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-07-4)

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 20℃;	51%
With copper(I) bromide; sodium nitrite

tert.-butylnitrite (540-80-7) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → 2-bromo-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-07-4)

Conditions	Yield
With copper(ll) bromide In acetonitrile at 20℃;	51%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → C25H18Cl3N9O2S2

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide With sodium t-butanolate In tetrahydrofuran at 0 - 20℃; for 1.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water	40%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → C15H12Cl2N6OS (1035343-44-2)

Conditions	Yield
With diisopropylamine In tetrahydrofuran at 0 - 20℃; for 2.5h;	33%
With diisopropylamine In tetrahydrofuran at 0 - 20℃; for 2.5h;	33%

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) + Tert-butyl isocyanate (1609-86-5) → 2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 1h;	28%

cyclopropanecarboxylic anhydride (33993-24-7) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → 2-[(Cyclopropylcarbonyl)amino]-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide

Conditions	Yield
In 1,4-dioxane at 93℃;	17%
In 1,4-dioxane at 93℃;	11 mg

2,4-dichloro-6-iso-butyl-1,3,5-triazine (536993-71-2) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → C18H18Cl2N6OS (1258411-45-8)

Conditions	Yield
With diisopropylamine In tetrahydrofuran at 0℃; for 6h;	9%

2-furancarbonyl chloride (527-69-5) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → N-(2-chloro-6-methylphenyl)-2-[(2-furanylcarbonyl)amino]-5-thiazolecarboxamide

Conditions	Yield
With dmap In tetrahydrofuran

cyclopropanecarboxylic acid chloride (4023-34-1) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → 2-[(Cyclopropylcarbonyl)amino]-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide

Conditions	Yield
With dmap In tetrahydrofuran

benzoyl chloride (98-88-4) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → 2-(benzoylamino)-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide

Conditions	Yield
With dmap In tetrahydrofuran

4-chloro-2-methylpyrimidine (4994-86-9) + 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5) → N-(2-chloro-6-methylphenyl)-2-(2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide

Conditions	Yield
With sodium hydride In tetrahydrofuran

Upstream product

• 17356-08-0 thiourea 
• 1044209-25-7 C₁₀H₁₀ClNO₂ 
• 34780-29-5 3-oxo-propionic acid ethyl ester 
• 87-63-8 2-chloro-6-methylaniline 
• 6191-99-7 3-ethoxyacryloyl chloride 
• 76758-01-5 N-tritylthiourea 
• 32955-21-8 2-amino-thiazole-5-carboxylic acid ethyl ester 
• 1416737-47-7 C₁₂H₁₅BrClNO₃ 
• 863127-76-8 (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide 
• 302964-06-3 [5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester 

Downstream Products

• 1035343-44-2 C₁₅H₁₂Cl₂N₆OS 
• 1323138-80-2 N-(2-chloro-6-methylphenyl)-2-(2-chloroacetamido)-5-thiazolecarboxamide 
• 1349900-64-6 N-(2-chloro-6-methylphenyl)-2-[2-(diethylamino)acetamido]-5-thiazolecarboxamide 
• 1323138-54-0 N-(2-chloro-6-methylphenyl)-2-[2-(pyrrolidin-1-yl)acetamido]-5-thiazolecarboxamide 
• 1323138-55-1 N-(2-chloro-6-methylphenyl)-2-[2-(piperidin-1-yl)acetamido]-5-thiazolecarboxamide 
• 1323138-58-4 N-(2-chloro-6-methylphenyl)-2-[2-(morpholin-4-yl)acetamido]-5-thiazolecarboxamide 
• 1323138-60-8 N-(2-chloro-6-methylphenyl)-2-[2-(4-methyl-1-piperazinyl)acetamido]-5-thiazolecarboxamide 
• 1323138-62-0 N-(2-chloro-6-methylphenyl)-2-[2-(4-(2-hydroxyethyl)-1-piperazinyl)acetamido]-5-thiazolecarboxamide 
• 1349900-65-7 N-(2-chloro-6-methylphenyl)-2-[2-(4-(4-chlorobenzoyl)-1-piperazinyl)acetamido]-5-thiazolecarboxamide 
• 1323138-63-1 2-(2-(azepan-1-yl)acetamido)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide 
• 863127-77-9 dasatinib monohydrate 
• 302962-49-8 dasatanib 
• 302964-08-5 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide 
• 302964-27-8 2-(6-chloro-pyrimidin-4-ylamino)-thiazole-5-carboxylic acid (2-chloro-6-methyl-phenyl)-amide 

Relevant articles and documents

SUBSTITUTED ARYLUREA COMPOUNDS FOR INDUCING APOPTOSIS AND COMPOSITION FOR ANTICANCER COMPRISING THE SAME

The present invention relates to a substituted arylurea compound inducing apoptosis and an anticancer composition comprising the same. The present invention relates to a novel compound capable of preventing, treating and alleviating cancer diseases such as prostate cancer, breast cancer, lung cancer, colorectal cancer, and skin cancer by inhibiting apoptosis of cancer cells and inhibiting proliferation of cancer cells.

Preparation process of dasatinib

The invention relates to a preparation process of dasatinib. The preparation process includes the following steps that 3-ethyl propionate reacts with 2-chlorine-6-methylaniline under an alkaline condition to obtain a compound 3; the compound 3, copper bromide and thiourea react under action of hydroxyethyl-beta-cyclodextrin to obtain 2-amino-N-(2-chlorine-6-methyl phenyl) thiazole-5-formamide through a heating reaction; secondly, 4,6-dichloro-2-methyl pyrimidine reacts with N-hydroxyethyl piperazine, 2-amino-N-(2-chloro-6-methyl phenyl) thiazole-5-formamide sequentially in the presence of alkali, a catalytic system and an organic solvent, and a compound 1, namely dasatinib, is obtained. The conditions are mild, the steps are simple, the process is environmentally friendly, the yield is high, and the process is suitable for industrial production.

Preparation method of dasatinib intermediate

The invention relates to a preparation method of a dasatinib intermediate. The method comprises the following steps: performing heating reflux on ethyl 3-oxopropanoate and 2-chloro-6-methylaniline under alkaline conditions, adding copper bromide, and performing warming reflux to obtain a compound 2; and cyclizing the compound 2 and thiourea in a solvent PEG 400 to obtain a target product, namely 2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. The method involved in the invention has mild conditions, simple steps, environmental friendliness and high yield, and is suitable for industrial production.