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

Uses

Used in Pharmaceutical Industry:
2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is used as a pharmaceutical compound for its antifungal and antimicrobial properties. It is being explored for its potential in treating various diseases and infections, making it a promising candidate for medicinal applications.
Used in Antifungal Applications:
In the pharmaceutical industry, 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is used as an antifungal agent to combat fungal infections. Its ability to inhibit fungal growth makes it a valuable component in the development of antifungal medications.
Used in Antimicrobial Applications:
2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is also used as an antimicrobial agent in the pharmaceutical industry. Its potential to inhibit the growth of bacteria and other microorganisms contributes to the development of new antimicrobial drugs and treatments.
Used in Disease and Infection Treatment Research:
In the pharmaceutical industry, 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is used as a research compound for exploring its potential in treating various diseases and infections. Its unique properties and activities make it a valuable asset in the search for new therapeutic solutions.

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

• 1044209-25-7 C₁₀H₁₀ClNO₂ 
• 17356-08-0 thiourea 
• 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

• 302961-18-8 N-(2-chloro-6-methylphenyl)-2-[(2,6-dimethyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide 
• 1035343-44-2 C₁₅H₁₂Cl₂N₆OS 

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The present invention provides a compound of formula 1 having an activity of inhibiting protein kinase and its use.

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.

A reach [...] preparation method

The invention relates to a preparation method of up to [...], the method comprises the following steps: 3 - ethyl oxo propionic acid under alkaline condition first with 2 - chloro - 6 - methylaniline reaction, then adding [...] copper solution reaction, to obtain compound 3; with the thiourea reaction, from 2 - amino - N - (2 - chloro - 6 - methyl phenyl) thiazole - 5 - carboxamide; after the 4, 6 - dichloro - 2 - methyl pyrimidine in alkali, catalytic system, organic solvents, successively with the N - hydroxyethyl piperazine, 2 - amino - N - (2 - chloro - 6 - methyl phenyl) thiazole - 5 - carboxamide reaction, to obtain compound 1, has reached the [...]. Mild condition of this invention, the step is simple, short reaction time, speed, friendly to the environment and have high yield, 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.

Preparation process of dasatinib

The invention relates to a preparation process of dasatinib. The method comprises the following steps: enabling 3-oxopropionic acid ethyl ester to react firstly with 2-chlo-6-methylaniline under an alkaline condition, then adding a solvent dissolved with cupric bromide, and reacting to obtain a compound 3; cyclizing the compound 3 and thiourea in solvent water to obtain 2-amino-N-(2-chlo-6-methylphenyl)thiazole-5-formamide; and then synthesizing dasatinib from 4,6-dichloro-2-methyl pyrimidine, N-ethoxyl piperazine, and 2-amino-N-(2-chlo-6-methyl phenyl)thiazole-5-formamide through a one-pot method under the actions of an alkali K3PO4 and a catalyst 1-butyl-3-methylimidazole glycinate. The conditions are mild, the steps are simple, and the preparation process is environmentally-friendly, high in yield and suitable for industrial production.

Method for preparing dasatinib tablets

The invention relates to a method for preparing dasatinib tablets. The method comprises the following steps: enabling 3-oxo-ethyl propionate to react with 2-chlorine-6-methylaniline under an alkali condition, further adding a solvent in which cupric bromide is dissolved to carry out a reaction, further adding thiourea, and cyclizing with a catalyst so as to obtain 2-amino-N-(2-chlorine-6-methyphenyl)thiazole-5-formamide; further synthesizing dasatinib tablets from 4,6-dichloro-2-methyl pyrimidine, N-ethoxy piperazine and 2-amino-N-(2-chlorine-6-methyphenyl)thiazole-5-formamide according to a one-pot method under the action of an alkali and an ionic liquid 1-butyl-3-methylimidazole glycinate. The method is mild in condition, simple in step, environmentally friendly, high in yield and applicable to industrial production.

Process for preparing dasatinib

The invention relates to a process for preparing dasatinib. The process includes steps of carrying out heating reflux on 3-oxo-propionic acid ethyl ester and 2-chlorine-6-methylaniline under alkalineconditions, adding cupric bromide, carrying out temperature-rise reflux, adding thiourea and a catalyst heteropoly acid salt, and carrying out room-temperature stirring reaction to obtain 2-amine-N-(2-chlorine-6-methyl phenyl)thiazole-5-formamide; carrying out 'one-pot reaction' on the 2-amine-N-(2-chlorine-6-methyl phenyl)thiazole-5-formamide, 4, 6-dichloro-2-methylpyrimidine and N-hydroxyethyl piperazine under the effects of catalysts to obtain the dasatinib. The process has the advantages of mild condition, simple step, environmental friendliness, high yield and applicability to industrialproduction.

Scalable and impurity-free process for dasatinib: Src and BCR-Abl inhibitor

An efficient, telescopic, impurity-free and scalable process for Bcr-Abl and Src family tyrosine kinase inhibitor for synthesis of Dasatinib with high yield and purity is described.

AN IMPROVED PROCESS FOR THE PREPARATION OF DASATINIB POLYMORPH

The present invention is related to an improved process for the preparation of dasatinib anhydrous crystalline Neat form N-6 with high purity and high yield. The present invention also relates to purification of dasatinib crystalline Neat form N-6.