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CAS No.: | 302962-49-8 |
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Name: | Dasatinib |
Article Data: | 47 |
Cas Database | |
Molecular Structure: | |
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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 |
Appearance: | pale-yellow solid |
PSA: | 134.75000 |
LogP: | 3.46240 |
1-(2-hydroxyethyl)piperazine
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
dasatanib
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% |
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide
dasatanib
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium methylate In methanol at 65℃; for 4h; Temperature; Cooling with ice; | 95.3% |
1-(2-hydroxyethyl)piperazine
2,4-dichloro-2-methylpyrimidine
2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
dasatanib
Conditions | Yield |
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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% |
1-(2-hydroxyethyl)piperazine
2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide
dasatanib
Conditions | Yield |
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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% |
2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol
2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
dasatanib
Conditions | Yield |
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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; |
C29H30ClN7O3S
dasatanib
Conditions | Yield |
---|---|
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% |
C29H32ClN7O2S
dasatanib
Conditions | Yield |
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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% |
1-(2-hydroxyethyl)piperazine
dasatanib
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 65 - 100℃; for 1h; Inert atmosphere; | 82% |
2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid
2-chloro-6-methylaniline
dasatanib
Conditions | Yield |
---|---|
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% |
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