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| CAS No.: | 152459-95-5 |
|---|---|
| Name: | Imatinib |
| Molecular Structure: | |
|
|
|
| Formula: | C29H31N7O |
| Molecular Weight: | 493.611 |
| Synonyms: | alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl amino)-p-tolu-p-toluidide;4-[(4-Methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide; |
| EINECS: | 604-855-6 |
| Density: | 1.256 g/cm3 |
| Melting Point: | 113°C |
| Boiling Point: | 451°C |
| Flash Point: | 196°C |
| Appearance: | off white powder |
| Hazard Symbols: |
 T, N
|
| Risk Codes: | R23/24/25; R40; R48/23/24; R51/53 |
| Safety: | 24/25 |
| PSA: | 86.28000 |
| LogP: | 4.61210 |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
| Conditions | Yield |
|---|---|
| Stage #1: 4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride; 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In water at 0℃; Stage #2: With sodium hydroxide In water at 50 - 55℃; pH=9 - 9.5; Product distribution / selectivity; | 99.26% |
| With pyridine at 0 - 20℃; for 1h; Product distribution / selectivity; | 95% |
| Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With pyridine for 0.333333h; Autoclave; Stage #2: 4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride at 0 - 25℃; for 8h; | 92.7% |
imatinib
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water at 0 - 55℃; pH=9 - 9.5; | 99.26% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 40 - 50℃; for 6h; Time; | 97.8% |
1-methyl-piperazine
4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide
imatinib
| Conditions | Yield |
|---|---|
| With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4.5h; Temperature; | 97.52% |
| In 1,4-dioxane at 135℃; for 3h; Conversion of starting material; | 91% |
| at 120 - 130℃; for 1.5h; Conversion of starting material; | 91% |
imatinib
| Conditions | Yield |
|---|---|
| With ammonia In water Product distribution / selectivity; | 97% |
4-[(4-methylpiperazin-1-yl)methyl]bromobenzene
carbon monoxide
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
| Conditions | Yield |
|---|---|
| With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 50℃; under 760.051 Torr; for 36h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 95.8% |
imatinib
| Conditions | Yield |
|---|---|
| With ammonia In water; isopropyl alcohol at 20℃; for 4h; pH=7.6 - 8.5; | 93% |
3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
imatinib
| Conditions | Yield |
|---|---|
| In butan-1-ol at 120 - 150℃; for 5h; Inert atmosphere; | 93% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
| Conditions | Yield |
|---|---|
| Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With pyridine; thionyl chloride at 50 - 60℃; for 3h; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine at -10 - 0℃; for 1h; | 92.5% |
| Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50℃; for 2h; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In N,N-dimethyl-formamide at 70℃; for 12h; | 91% |
| Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With pyridine; thionyl chloride at 20 - 50℃; for 1 - 2h; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With pyridine at 0 - 25℃; for 1h; Product distribution / selectivity; | 90% |
N-(3-bromo-4-methylphenyl)-4-((4-methylpiperazin-1-yl)-methyl)benzamide
4-pyridin-3-ylpyrimidin-2-ylamine
imatinib
| Conditions | Yield |
|---|---|
| With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 5h; Temperature; | 92% |
| Stage #1: N-(3-bromo-4-methylphenyl)-4-((4-methylpiperazin-1-yl)-methyl)benzamide; 4-pyridin-3-ylpyrimidin-2-ylamine In ethanol at 60℃; for 3h; Inert atmosphere; Stage #2: With sodium hydroxide In water pH=8.7; Reagent/catalyst; | 91% |
| With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 5.16667h; Inert atmosphere; Reflux; Sonication; | 72% |
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Imatinib (CAS NO.152459-95-5) was developed by rational drug design. After the Philadelphia chromosome mutation and defective bcr-abl protein were discovered, the investigators screened chemical libraries to find a drug that would inhibit that protein. They identified 2-phenylaminopyrimidine with high-throughput screening, then it is tested and modified by the introduction of methyl and benzamide groups to give it enhanced binding properties, producing Imatinib.
1. Introduction of Imatinib
Imatinib is one kind of white to off-white crystalline or pale yellow powder. The IUPAC Name of this chemical is 4-[(4-Methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide. Besides, Imatinib belongs to Molecular Targeted Antineoplastic;Pharmaceutical intermediate;Imatinib. In addition, the Classification Code of this chemical is Antineoplastic; Antineoplastic Agents; Enzyme Inhibitors; Protein Kinase Inhibitors. Imatinib is very soluble in water at pH < 5.5 (mesylate salt). It should be stored at refrigerator.
2. Properties of Imatinib
Physical properties about Imatinib are:
(1)Index of Refraction: 1.671; (2)Surface Tension: 63.6 dyne/cm; (3)Density: 1.255 g/cm3; (4)H bond acceptors: 8; (5)H bond donors: 2; (6)Freely Rotating Bonds: 6; (7)Polar Surface Area: 68.7 Å2; (8)Index of Refraction: 1.671; (9)Molar Refractivity: 147.09 cm3; (10)Molar Volume: 393 cm3; (11)XLogP3-AA: 3.5; (12)H-Bond Donor: 2; (13)H-Bond Acceptor: 7; (14)Rotatable Bond Count: 7; (15)Tautomer Count: 6; (16)Exact Mass: 493.259009; (17)MonoIsotopic Mass: 493.259009; (18)Topological Polar Surface Area: 86.3; (19)Heavy Atom Count: 37; (20)Formal Charge: 0; (21)Complexity: 706; (22)Isotope Atom Count: 0; (23)Defined Atom Stereocenter Count: 0; (24)Undefined Atom Stereocenter Count: 0; (25)Defined Bond Stereocenter Count: 0; (26)Undefined Bond Stereocenter Count: 0; (27)Covalently-Bonded Unit Count: 1; (28)Feature 3D Acceptor Count: 3; (29)Feature 3D Donor Count: 2; (30)Feature 3D Cation Count: 3; (31)Feature 3D Ring Count: 5; (32)Effective Rotor Count: 9.2; (33)Conformer Sampling RMSD: 1.
3. Structure Descriptors of Imatinib
(1)SMILES: O=C(Nc3ccc(c(Nc2nc(c1cccnc1)ccn2)c3)C)c4ccc(cc4)CN5CCN(CC5)C
InChI: InChI=1/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
(2)InChIKey: KTUFNOKKBVMGRW-UHFFFAOYAJ
(3)Std. InChI: InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
(4)Std. InChIKey: KTUFNOKKBVMGRW-UHFFFAOYSA-N
4. Uses of Imatinib
Imatinib is used in chronic myelogenous leukemia (CML), gastrointestinal stromal tumors (GISTs) and a number of other malignancies. Imatinib (originally STI571) is a drug used to treat certain cancers. It is the first member of a new class of agents that act by inhibiting particular tyrosine kinase enzymes, instead of non-specifically inhibiting rapidly dividing cells.
5. Production of Imatinib
N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine and 4-(4-Methylpiperazin-1-ylmethyl)benzoyl chloride can used to manufacture Imatinib when them are soluble in Azabenzene. And the condition of this reaction can be taken place under the room temperature and nitrogen. Then stir them, reduced pressure concentration, add water, cooling, filter, filter cake vacuum drying, join methylene chloride - methanol, and filtering. At last, you can get the Imatinib.
