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302962-49-8

Basic Information
CAS No.: 302962-49-8
Name: 5-Thiazolecarboxamide,N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-
Article Data: 47
Cas Database
Molecular Structure:
Molecular Structure of 302962-49-8 (5-Thiazolecarboxamide,N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-)
Formula: C22H26ClN7O2S
Molecular Weight: 488.013
Synonyms: BMS 354825;BMS 35482513;Sprycel;Spyrcel;N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide;
EINECS: 801-607-0
Density: 1.409 g/cm3
Melting Point: 275-286 °C
Boiling Point: N/A
Flash Point: N/A
Solubility: N/A
Appearance: pale-yellow solid
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 134.75000
LogP: 3.46240
Synthetic route
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
ConditionsYield
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%
1245157-85-0

N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide

302962-49-8

dasatanib

Conditions
ConditionsYield
With potassium carbonate In methanol; water at 60 - 65℃; for 3h; Solvent; Reagent/catalyst;96.4%
Stage #1: N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
88.7%
Stage #1: N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
88.7%

C20H24ClN5O4S

124-42-5

acetamidine hydrochloride

302962-49-8

dasatanib

Conditions
ConditionsYield
With sodium methylate In methanol at 65℃; for 4h; Temperature; Cooling with ice;95.3%
103-76-4

1-(2-hydroxyethyl)piperazine

1780-26-3

2,4-dichloro-2-methylpyrimidine

302964-24-5

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

302962-49-8

dasatanib

Conditions
ConditionsYield
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%
103-76-4

1-(2-hydroxyethyl)piperazine

1245157-51-0

2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide

302962-49-8

dasatanib

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol for 7h; Solvent; Time; Reflux;87.9%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 5h; Product distribution / selectivity; Reflux;73.6%
127116-19-2

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol

302964-24-5

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

302962-49-8

dasatanib

Conditions
ConditionsYield
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;
1245157-86-1

C29H30ClN7O3S

302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C29H30ClN7O3S With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
82.5%
Stage #1: C29H30ClN7O3S With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
82.5%
1245157-70-3

C29H32ClN7O2S

302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C29H32ClN7O2S With boron trichloride In dichloromethane at -15 - 20℃;
Stage #2: With water In dichloromethane Cooling with ice;
82.2%
With boron trichloride In dichloromethane at -15 - 20℃;82.2%
103-76-4

1-(2-hydroxyethyl)piperazine

(2-(6-chloro-2-methylpyrimidine-4-ylamino)-N-(2-chloro-6-methylpbenyl)thiazole-5-carboxamide)

302962-49-8

dasatanib

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 65 - 100℃; for 1h; Inert atmosphere;82%
1245157-42-9

2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid

87-63-8

2-chloro-6-methylaniline

302962-49-8

dasatanib

Conditions
ConditionsYield
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Product distribution / selectivity; Inert atmosphere;80.9%
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Reagent/catalyst; Inert atmosphere;80.9%
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863127-77-9
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Specification

The CAS register number of 5-Thiazolecarboxamide,N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]- is 302962-49-8. It also can be called as Dasatinib and the IUPAC name about this chemical is N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide. The molecular formula about this chemical is C22H26ClN7O2S and the molecular weight is 488.01. It belongs to the following product categories, such as Intermediates & Fine Chemicals; Pharmaceuticals; Tyrosine Kinase Inhibitors; Pharmaceutical intermediate and so on. This chemical is used as a new, oral, small-molecule Tyrosine Kinase Inhibitor (TKI) for the treatment of CML and antineoplastic.

Physical properties about 5-Thiazolecarboxamide,N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]- are: (1)ACD/LogP: 0.14; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 11.084; (6)#H bond acceptors: 9; (7)#H bond donors: 3; (8)#Freely Rotating Bonds: 6; (9)Polar Surface Area: 134.75Å2; (10)Index of Refraction: 1.688; (11)Molar Refractivity: 132.039 cm3; (12)Molar Volume: 346.405 cm3; (13)Polarizability: 52.344x10-24cm3; (14)Surface Tension: 73.791 dyne/cm.

The 5-Thiazolecarboxamide,N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]- is a cancer drug produced by Bristol-Myers Squibb and sold under the trade name Sprycel. It is an oral dual BCR/ABL and Src family tyrosine kinases inhibitor approved for use in patients with chronic myelogenous leukemia (CML) after imatinib treatment and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL). It is also being assessed for use in metastatic melanoma.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1cccc(c1NC(=O)c2cnc(s2)Nc3cc(nc(n3)C)N4CCN(CC4)CCO)Cl
(2)InChI: InChI=1/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
(3)InChIKey: ZBNZXTGUTAYRHI-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
(5)Std. InChIKey: ZBNZXTGUTAYRHI-UHFFFAOYSA-N