N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide supplier

Name
N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide
EINECS
CAS No. 302964-08-5
Article Data26
CAS DataBase
Density 1.516 g/cm³
Solubility
Melting Point 333-335°C
Formula C₁₆H₁₃Cl₂N₅OS
Boiling Point
Molecular Weight 394.284
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-[(6-Chloro-2-methylpyrimidin-4-yl)amino]-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide;
PSA 108.04000
LogP 4.99860

Synthetic route

: 834888-64-1
N-(4-methoxybenzyl)-2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane at 20℃; for 3h;	99%
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane at 20℃; for 3h;	99%
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane at 20℃; for 9h; Inert atmosphere;	97.6%
With trifluorormethanesulfonic acid; trifluoroacetic acid Inert atmosphere;	97%

: 1780-26-3
2,4-dichloro-2-methylpyrimidine

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

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

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%

: N-(2-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)-amino]-5-thiazolecarboxamide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
With N-chloro-succinimide; palladium dichloride In acetonitrile at 100℃; for 12h;	96.8%

: N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 126827-01-8
N-(6-chloro-2-methylpyrimidin-4-yl)hydroxylamine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide at 100℃; for 5h; Temperature;	95%

: 6307-67-1
2-chloro-N-(2-chloro-6-methylphenyl)acetamide

: C9H12ClN5S

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
In methanol for 24h; Solvent; Reflux;	74%

: 77296-31-2
1-(6-chloro-2-methylpyrimidin-4-yl)thiourea

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In tetrahydrofuran; water at 0 - 22℃; for 3h; Stage #2: 1-(6-chloro-2-methylpyrimidin-4-yl)thiourea In tetrahydrofuran; water for 2h; Heating / reflux;	71%
Multi-step reaction with 2 steps 1: ethanol / 4 h 2: methanol / 24 h / Reflux View Scheme

: 1749-68-4
4-amino-6-chloro-2-methylpyrimidine

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

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
With sodium hydride

: 40398-01-4
2-chloro-6-methylphenyl isocyanate

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 - -75 °C 1.2: 86 percent / tetrahydrofuran; hexane / 2 h / -78 °C 2.1: NaH / dimethylformamide / 0.5 h 2.2: 95 percent / Bu4NI / dimethylformamide / 16 h / 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 3.2: 83 percent / tetrahydrofuran / 4 h / Heating 4.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 86 percent / tetrahydrofuran; hexane / 2 h / -78 °C 2.1: NaH / dimethylformamide / 0.5 h / 20 °C 2.2: 95 percent / tetrabutylammonium iodide / dimethylformamide / 16 h / 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 3.2: 83 percent / tetrahydrofuran / 4 h / Heating 4.1: 99 percent / TFA; triflic acid / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere 2.1: caesium carbonate / acetone / 10 h / Reflux; Inert atmosphere 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 4 h / Reflux; Inert atmosphere 4.1: trifluorormethanesulfonic acid; trifluoroacetic acid / dichloromethane / 9 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran / Inert atmosphere 4.1: trifluorormethanesulfonic acid; trifluoroacetic acid / Inert atmosphere View Scheme

: 302964-11-0
2-chloro-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: 95 percent / Bu4NI / dimethylformamide / 16 h / 20 °C 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 83 percent / tetrahydrofuran / 4 h / Heating 3.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 0.5 h / 20 °C 1.2: 95 percent / tetrabutylammonium iodide / dimethylformamide / 16 h / 20 °C 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 83 percent / tetrahydrofuran / 4 h / Heating 3.1: 99 percent / TFA; triflic acid / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 4 h / Reflux; Inert atmosphere 3.1: trifluorormethanesulfonic acid; trifluoroacetic acid / dichloromethane / 9 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / Inert atmosphere 2: sodium hydride / tetrahydrofuran / Inert atmosphere 3: trifluorormethanesulfonic acid; trifluoroacetic acid / Inert atmosphere View Scheme

: 834888-63-0
N-(4-methoxybenzyl)-2-chloro-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 1.2: 83 percent / tetrahydrofuran / 4 h / Heating 2.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 1.2: 83 percent / tetrahydrofuran / 4 h / Heating 2.1: 99 percent / TFA; triflic acid / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 4 h / Reflux; Inert atmosphere 2.1: trifluorormethanesulfonic acid; trifluoroacetic acid / dichloromethane / 9 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / Inert atmosphere View Scheme

: 87-63-8
2-chloro-6-methylaniline

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: i-Pr2NEt / tetrahydrofuran 2: TFA / CH2Cl2 3: NaH / tetrahydrofuran View Scheme
Multi-step reaction with 4 steps 1: i-Pr2NEt / tetrahydrofuran 2: TFA / CH2Cl2 3: NaNO2; CuBr 4: NaH View Scheme
Multi-step reaction with 3 steps 1: pyridine / tetrahydrofuran 2: N-Bromosuccinimide / -10 - 80 °C 3: sodium t-butanolate / tetrahydrofuran / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: N-chloro-succinimide / acetonitrile / 1.5 h 2: iron(III) chloride; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide / acetonitrile; water / 5 h / 80 °C 3: sodium methylate / N,N-dimethyl-formamide / 5 h / 100 °C View Scheme

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

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaNO2; CuBr 2: NaH View Scheme

: 302964-06-3
[5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 2: NaH / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 2: NaNO2; CuBr 3: NaH View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane 2: sodium t-butanolate / dichloromethane View Scheme
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / 2 h / 25 - 30 °C 2.1: sodium t-butanolate / tetrahydrofuran / 10 - 20 °C 2.2: 2 h / 0 - 5 °C / pH 2 - 3 View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 25 - 30 °C 2: sodium t-butanolate / tetrahydrofuran / 10 - 30 °C / Inert atmosphere View Scheme

: 1780-26-3
2,4-dichloro-2-methylpyrimidine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane; isopropyl alcohol / 20 h / 20 °C 2.1: triethylamine / tetrahydrofuran; water / 0.17 h / 120 °C / Microwave irradiation 2.2: 0.17 h / 20 °C 3.1: tert.-butylhydroperoxide; sodium iodide / water / 4 h / 80 °C / Inert atmosphere 4.1: N-chloro-succinimide; palladium dichloride / acetonitrile / 12 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; triethylamine / ethanol / 1.5 h / 110 °C 2: sodium methylate / N,N-dimethyl-formamide / 5 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 72 h / 0 - 20 °C / Inert atmosphere 2: sodium hydroxide; water / methanol; water / 16 h / 20 °C 3: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere View Scheme

: C13H11ClN4OS

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol; water / 2 h / 60 °C 2: methanol / 4 h 3: methanol / 24 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol; water / 2 h / 60 °C 2: ethanol / 4 h 3: methanol / 24 h / Reflux View Scheme

: 1749-68-4
4-amino-6-chloro-2-methylpyrimidine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / 24 h / Reflux 2: sodium hydroxide / 2 h / 50 °C 3: methanol / 4 h 4: methanol / 24 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: tetrahydrofuran / 24 h / Reflux 2: sodium hydroxide / 2 h / 50 °C 3: ethanol / 4 h 4: methanol / 24 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: tetrahydrofuran / 8 h / Reflux 2: sodium hydroxide / methanol; water / 2 h / 60 °C 3: methanol / 4 h 4: methanol / 24 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: tetrahydrofuran / 8 h / Reflux 2: sodium hydroxide / methanol; water / 2 h / 60 °C 3: ethanol / 4 h 4: methanol / 24 h / Reflux View Scheme

: 77296-30-1
6-chloro-2-methylpyrimidin-4-ylcarbamothioylcarbamate

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / 2 h / 50 °C 2: methanol / 4 h 3: methanol / 24 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / 2 h / 50 °C 2: ethanol / 4 h 3: methanol / 24 h / Reflux View Scheme

: 863127-76-8
(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / water; 1,4-dioxane / 3 h / 25 - 30 °C 1.2: 2 h / 25 - 70 °C 2.1: sodium t-butanolate / tetrahydrofuran / 8 h / 5 - 30 °C View Scheme

: N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / -10 - 80 °C 2: sodium t-butanolate / tetrahydrofuran / 0 - 5 °C View Scheme

: 1034919-70-4
(6-chloro-2-methylpyrimidin-4-yl)thiazol-2-yl-amine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran; water / 0.17 h / 120 °C / Microwave irradiation 1.2: 0.17 h / 20 °C 2.1: tert.-butylhydroperoxide; sodium iodide / water / 4 h / 80 °C / Inert atmosphere 3.1: N-chloro-succinimide; palladium dichloride / acetonitrile / 12 h / 100 °C View Scheme

: 2-(6-chloro-2-methylpyrimidine-4-yl)amino-5-hydroxymethylthiazole

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide; sodium iodide / water / 4 h / 80 °C / Inert atmosphere 2: N-chloro-succinimide; palladium dichloride / acetonitrile / 12 h / 100 °C View Scheme

: C7H7Cl2N

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: iron(III) chloride; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide / acetonitrile; water / 5 h / 80 °C 2: sodium methylate / N,N-dimethyl-formamide / 5 h / 100 °C View Scheme

: 1202357-66-1
ethyl 2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-1,3-thiazole-5-carboxylate

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; water / methanol; water / 16 h / 20 °C 2: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere View Scheme

: 2-((6-chloro-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxylic acid

: 87-63-8
2-chloro-6-methylaniline

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
With N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Inert atmosphere;	480 mg

: 110-85-0
piperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 910297-51-7
N-(2-chloro-6-methylphenyl)-2-((2-methyl-6-(piperazin-1-yl)pyrimidin 4-yl)amino)thiazole-5-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 4h;	98%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 110 - 120℃;	81.2%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 110℃; for 16h; Inert atmosphere;	80%

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 302962-49-8
dasatanib

Conditions

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile at 30 - 80℃;	97%
In propan-1-ol at 115 - 120℃; Temperature;	93%
With copper(l) chloride In N,N-dimethyl-formamide at 65℃; for 2h; Temperature; Reagent/catalyst;	91.6%

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 65-71-4
thymin

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: dasatinib-thymine

Conditions

Conditions	Yield
In methanol at 25 - 67℃; Solvent;	91.38%

...Expand

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: Dasatinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-(2-hydroxyethyl)piperazine; 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide With N-ethyl-N,N-diisopropylamine In 1,4-dioxane for 12h; Reflux; Stage #2: With hydrogenchloride In water	91%

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: tbutyl 4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h;	89%
Stage #1: 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: 1-t-Butoxycarbonylpiperazine In N,N-dimethyl-formamide at 110℃; for 16h;	89.9%
With N-ethyl-N,N-diisopropylamine In pentan-1-ol for 8h; Reflux;	84%
With triethylamine In N,N-dimethyl-formamide at 80℃;	56.28%

: 40004-08-8
1-(Ethoxycarbonylmethyl)piperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 910297-62-0
ethyl 2-(4-(6-(5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-ylamino)-2-methylpyrimidin-4-yl)piperazin-1-yl)acetate

Conditions

Conditions	Yield
In ethanol at 20 - 150℃; for 1.75h; Microwave irradiation;	89%
In ethanol at 150℃; for 0.75h; Irradiation;	89%

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: N-(2-chloro-6-methylphenyl)-2-(6-(4-(3-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino) thiazole-5-carboxamide ethanolate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 110℃; for 0.416667h;	88.7%

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 910297-51-7
N-(2-chloro-6-methylphenyl)-2-((2-methyl-6-(piperazin-1-yl)pyrimidin 4-yl)amino)thiazole-5-carboxamide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20 - 80℃; for 1h; Inert atmosphere;	86%

: 622-26-4
4-(2-Hydroxyethyl)piperidine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperidin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 16h;	84%

: methyl piperidine-4-acetate hydrochloride

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: C24H27ClN6O3S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 16h;	84%

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 863127-77-9
dasatinib monohydrate

Conditions

Conditions	Yield
Stage #1: 1-(2-hydroxyethyl)piperazine; 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide With N-ethyl-N,N-diisopropylamine In butan-1-ol at 118℃; for 4.5h; Stage #2: With water In ethanol	83.2%
Stage #1: 1-(2-hydroxyethyl)piperazine; 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 2.5h; Stage #2: With water In N,N-dimethyl-formamide at 20 - 100℃; for 2h;

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 123-51-3
i-Amyl alcohol

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1613319-06-4
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazole carboxamide isoamyl alcohol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 140℃; for 6h; Inert atmosphere;	81%

...Expand

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 872-50-4
1-methyl-pyrrolidin-2-one

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1613319-05-3
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazole carboxamide N-methyl-2-pyrrolidone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 90℃; for 1.16667h; Inert atmosphere;	80%

...Expand

: 7755-92-2
piperazine-1-carbaldehyde

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: N-(2-chloro-6-methylphenyl)-2-((6-(4-formylpiperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80 - 85℃; for 5h;	79%

: 107-15-3
ethylenediamine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 910297-59-5
2-({6-[(2-aminoethyl)amino]-2-methylpyrimidin-4-yl}amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
In 1,4-dioxane for 90h; Inert atmosphere;	76.2%
at 120℃; for 6h; Inert atmosphere;	57%

: 186550-13-0
3-amino-1-(t-butoxycarbonyl)pyrrolidine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: C25H30ClN7O3S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 12h;	75%

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1229345-36-1
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazole carboxamide N,N-dimethylformamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 90℃; for 3h; Inert atmosphere;	73%

...Expand

: 108-42-9
3-chloro-aniline

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1587622-91-0
C22H18Cl2N6OS

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 110℃; for 12h;	73%

: 106-47-8
4-chloro-aniline

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1587623-11-7
N-(2-chloro-6-methylphenyl)-2-((6-((4-chlorophenyl)amino)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 110℃; for 12h;	73%

: 6315-89-5
3,4-dimethoxyaniline

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1587622-97-6
N-(2-chloro-6-methylphenyl)-2-((6-((3,4-dimethoxyphenyl)amino)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 110℃; for 12h;	69%

: 186550-13-0
3-amino-1-(t-butoxycarbonyl)pyrrolidine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: C20H22ClN7OS

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20 - 80℃; for 1h; Inert atmosphere;	68%

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 67-68-5
dimethyl sulfoxide

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1228188-51-9
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazole carboxamide dimethylsulfoxide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 90℃; for 3h; Inert atmosphere;	67%

...Expand

: 104-94-9
4-methoxy-aniline

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1587622-96-5
N-(2-chloro-6-methylphenyl)-2-((6-((4-methoxyphenyl)amino)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 110℃; for 12h;	67%

: 656-65-5
3-fluoro-4-bromophenylamine

: 302964-08-5
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

: 1587622-95-4
2-((6-((4-bromo-3-fluorophenyl)amino)-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 110℃; for 12h;	59%

N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide Specification

The N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide, with the CAS registry number 302964-08-5, is also known as 5-Thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-. It belongs to the product categories of Dasatinib; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds. This chemical's molecular formula is C₁₆H₁₃Cl₂N₅OS and molecular weight is 394.28. Its systematic name is called N-(2-chloro-6-methylphenyl)-2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-1,3-thiazole-5-carboxamide. This chemical can be used as dasatinib intermediate and protein tyrosine kinase inhibitor.

Physical properties of N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide: (1)ACD/LogP: 2.46; (2)ACD/LogD (pH 5.5): 2.46; (3)ACD/LogD (pH 7.4): 2.46; (4)ACD/BCF (pH 5.5): 43.58; (5)ACD/BCF (pH 7.4): 43.57; (6)ACD/KOC (pH 5.5): 518.8; (7)ACD/KOC (pH 7.4): 518.65; (8)#H bond acceptors: 6; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.716; (12)Molar Refractivity: 102.3 cm³; (13)Molar Volume: 259.9 cm³; (14)Surface Tension: 70.3 dyne/cm; (15)Density: 1.516 g/cm³.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cccc(c1NC(=O)c2sc(nc2)Nc3nc(nc(Cl)c3)C)C
(2)InChI: InChI=1/C16H13Cl2N5OS/c1-8-4-3-5-10(17)14(8)23-15(24)11-7-19-16(25-11)22-13-6-12(18)20-9(2)21-13/h3-7H,1-2H3,(H,23,24)(H,19,20,21,22)
(3)InChIKey: LMXUWARKUIELGT-UHFFFAOYAU

Product Name

N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide

Synthetic route

N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide Specification

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