CAS No.641571-10-0,Nilotinib Suppliers

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Basic Information

Molecular Structure:
CAS No.:	641571-10-0
Name:	Nilotinib
Article Data:	29

Formula:	C₂₈H₂₂F₃N₇O
Molecular Weight:	529.524
Synonyms:	4-methyl-N-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzamide;4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-N-[5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl]benzamide;AMN-107;AMN107;Benzamide, 4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-(4-(3-pyridinyl)-2-pyrimidinyl)amino)-;AMN 107;Nilotinib(TINIBS );Nilotinib & its intermediates;Nilotinib hydrochloride monohydrate;
EINECS:	700-544-5
Density:	1.362 g/cm³
Melting Point:	231-233 °C
Appearance:	off-white solid
PSA:	97.62000
LogP:	6.50180

Synthetic route

: 641571-11-1
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

: 201230-82-2
carbon monoxide

: 5-bromo-2-methylphenyl(4-(pyridin-3-yl)pyrimidin-2-yl)-carbamic acid tert-butyl ester

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
Stage #1: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline; carbon monoxide; 5-bromo-2-methylphenyl(4-(pyridin-3-yl)pyrimidin-2-yl)-carbamic acid tert-butyl ester With bis(benzonitrile)palladium(II) dichloride; triethylamine; 1,2-bis-(diphenylphosphino)ethane; phenol In N,N-dimethyl-formamide at 90 - 105℃; under 6000.6 Torr; for 48h; Molecular sieve; Inert atmosphere; Autoclave; Stage #2: With trifluoroacetic acid In ethanol Inert atmosphere; Stage #3: With potassium hydroxide In ethanol; water pH=6 - 9; Reagent/catalyst; Solvent; Pressure; Inert atmosphere;	100%

Yield

Stage #1: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline; carbon monoxide; 5-bromo-2-methylphenyl(4-(pyridin-3-yl)pyrimidin-2-yl)-carbamic acid tert-butyl ester With bis(benzonitrile)palladium(II) dichloride; triethylamine; 1,2-bis-(diphenylphosphino)ethane; phenol In N,N-dimethyl-formamide at 90 - 105℃; under 6000.6 Torr; for 48h; Molecular sieve; Inert atmosphere; Autoclave;
Stage #2: With trifluoroacetic acid In ethanol Inert atmosphere;
Stage #3: With potassium hydroxide In ethanol; water pH=6 - 9; Reagent/catalyst; Solvent; Pressure; Inert atmosphere;

100%

...Expand

: 4-methyl-N-[3-(4-methyl-1H-imidazolyl)-5-trifluoromethylphenyl]-3-guanidinobenzamide nitrate

: 55314-16-4, 75415-01-9, 123367-26-0
3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 40h; Reagent/catalyst; Reflux;	95.2%

: 641571-11-1
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

: 641569-94-0
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In 1-methyl-pyrrolidin-2-one at 60℃; for 1.25h; Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In 1-methyl-pyrrolidin-2-one at 90℃; for 3h; Product distribution / selectivity;	94%
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In 1-methyl-pyrrolidin-2-one at 60℃; for 1.25h; Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In 1-methyl-pyrrolidin-2-one at 90℃; for 3h; Stage #3: With sodium hydroxide In 1-methyl-pyrrolidin-2-one; water at 80℃; pH=11 - 12; Product distribution / selectivity;	94%
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In 1-methyl-pyrrolidin-2-one at 60℃; for 1.5h; Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In 1-methyl-pyrrolidin-2-one at 90℃; for 0.5h;	90%

: 641571-11-1
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

: 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
With trimethylaluminum In toluene for 5h; Concentration; Time; Reflux;	91%

: 641571-11-1
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

: 917392-54-2
methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;	90%
With sodium t-butanolate In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;	81%
With potassium tert-butylate In tetrahydrofuran at -5 - 20℃; for 30h; Inert atmosphere; Large scale;	68%

: nilotinib trihydrochloride

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 45 - 70℃;	90%
With sodium hydroxide In methanol; water at 45 - 70℃;	90%

: 55314-16-4, 75415-01-9, 123367-26-0
3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / butan-1-ol / 12 h / Inert atmosphere; Reflux 2: C43H63ClNO2PPd; caesium carbonate / 1,4-dioxane / 1.5 h / 120 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / butan-1-ol / 12 h / Inert atmosphere; Reflux 2: C43H63ClNO2PPd; caesium carbonate / 1,4-dioxane / 1.5 h / 120 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 4: 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate / 1,4-dioxane / 12 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide / butan-1-ol / 12 h / Inert atmosphere; Reflux 1.2: 0.33 h / 25 - 125 °C 1.3: 1 h / 25 - 35 °C 2.1: Carbonyldiimidazole; 1H-imidazole hydrochloride / 1-methyl-pyrrolidin-2-one / 2 h / 20 - 55 °C / Inert atmosphere 2.2: 24 h / 50 - 105 °C / Inert atmosphere View Scheme

: 66521-66-2
4-pyridin-3-ylpyrimidin-2-ylamine

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: C43H63ClNO2PPd; caesium carbonate / 1,4-dioxane / 1.5 h / 120 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: C43H63ClNO2PPd; caesium carbonate / 1,4-dioxane / 1.5 h / 120 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 3: 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate / 1,4-dioxane / 12 h / 120 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 2 steps
1: C43H63ClNO2PPd; caesium carbonate / 1,4-dioxane / 1.5 h / 120 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere
View Scheme

Multi-step reaction with 3 steps
1: C43H63ClNO2PPd; caesium carbonate / 1,4-dioxane / 1.5 h / 120 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere
3: 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate / 1,4-dioxane / 12 h / 120 °C / Inert atmosphere
View Scheme

: 54962-75-3
[3-bromo-5-(trifluoromethyl)phenyl]amine

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate / 1,4-dioxane; toluene / 12 h / 120 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; 8-quinolinol; potassium carbonate / dimethyl sulfoxide / 18 h / 120 °C / Inert atmosphere; Sealed tube 2: sodium t-butanolate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: copper(l) iodide; 8-quinolinol; potassium carbonate / dimethyl sulfoxide / 18 h / 120 °C / Inert atmosphere; Sealed tube 2.1: thionyl chloride; N,N-dimethyl-formamide / 6 h / Reflux 2.2: 6 h / 0 - 20 °C View Scheme

: 55314-16-4, 75415-01-9, 123367-26-0
(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

: 641571-10-0
nilotinib

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / butan-1-ol / 24 h / Reflux 2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; tert-butyl alcohol / 7 h / 100 °C View Scheme

Raw Materials

350-03-8

Downstream Products

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History

Chemists created nilotinib with the idea of improving the target specificity of an earlier kinase inhibitor, imatinib. Novartis, the manufacturer, says Nilotinib caused a hematologic response in 74% of cases in clinical trials for use on Ph+ CML leukemia. It appears that these drugs seem to improve the action of cancer treatment in certain conditions, but actually have detrimental effects in other conditions. In October 2007, the FDA approved Nilotinib for CML. In June 2008 Italian doctors presented evidence of the efficacy and tolerability of nilotinib in CLL. The complete cytogenic response among patients in their tests was 84%.

Specification

1. Introduction of Nilotinib
Nilotinib is one kind of white to off white powder or off-white solid. The IUPAC Name of this chemical is 4-Methyl-N-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzamide. Besides, Nilotinib belongs to API; Molecular Targeted Antineoplastic; Nucleotides and Nucleosides; Bases & Related Reagents; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals; Pharmaceutical intermediate. In addition, the Classification Code of Nilotinib is Antineoplastic; Antineoplastic Agents. What's more, Nilotinib is sparingly soluble in ethanol and methanol.

2. Properties of Nilotinib
Physical properties about Nilotinib are:
(1)XLogP3-AA: 4.9; (2)H-Bond Donor: 2; (3)H-Bond Acceptor: 9; (4)Water solubility: 2.01e-03 g/l; (5)LogP: 4.51; (6)LogP: 4.41; (7)LogS: -5.4; (8)PKa: 13.47; (9)Hydrogen acceptor count: 6; (10)Hydrogen donor count: 2; (11)Polar surface area: 97.62; (12)Rotatable bond count: 7; (13)Refractivity: 152.85; (14)Polarizability: 52.35; (15)Index of Refraction: 1.649; (16)Molar Refractivity: 141.75 cm³; (17)Molar Volume: 388.6 cm³; (18)Polarizability: 56.19 10^-24cm³; (19)Surface Tension: 47.4 dyne/cm.

3. Structure Descriptors of Nilotinib
(1)InChI: InChI=1S/C28H22F3N7O/c1-17-5-6-19(10-25(17)37-27-33-9-7-24(36-27)20-4-3-8-32-14-20)26(39)35-22-11-21(28(29,30)31)12-23(13-22)38-15-18(2)34-16-38/h3-16H,1-2H3,(H,35,39)(H,33,36,37)
(2)InChIKey: HHZIURLSWUIHRB-UHFFFAOYSA-N
(3)Canonical SMILES : CC1=C(C=C(C=C1)C(=O)NC2=CC(=CC(=C2)N3C=C(N=C3)C)C(F)(F)F)NC4=NC=CC(=N4)C5=CN=CC=C5
(4)Smiles: c1c(cc(cc1n1cc(nc1)C)NC(=O)c1cc(c(cc1)C)Nc1nccc(n1)c1cccnc1)C(F)(F)F

4. Safety information of Nilotinib
Nilotinib may cause QTc prolongation , such as an irregular heart rhythm that can lead to fainting, loss of consciousness, seizures, or sudden death.

5. Uses of Nilotinib
Nilotinib is a selective Bcr/Abl tyrosine kinase inhibitor with the form of the hydrochloride monohydrate salt. Nilotinib is an analog of Imatinib with similar multiple kinase targets, but without inhibition of the Src gene. Nilotinib (CAS NO.641571-10-0) is used in treatment of leukemia (specifically chronic myeloid leukemia). In that study 92% of patients (already resistant or unresponsive to Gleevec) achieved a normal white blood cell counts after five months of treatment. The drug carries a black box warning for possible heart complications.