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molecular formula C28H23ClF3N7O B1258797 Nilotinib hydrochloride CAS No. 923288-95-3

Nilotinib hydrochloride

Cat. No. B1258797
M. Wt: 566.0 g/mol
InChI Key: VTGGYCCJUPYZSX-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08829015B2

Procedure details

4.0 g 4-methyl-N-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide free base is dissolved in 60 mL methanol at 50° C. 1.05 equivalent (688.7 μL) of hydrochloric acid is added as a solution in 2 mL of methanol. The solution is let stand for 60 minutes at 50° C. The solution is cooled down to 42° C. and kept at this temperature for 15 minutes. A suspension of 4 mg of 4-methyl-N-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide hydrochloride in methanol (40 mg)/water (0.4 mg) homogenized for 10 seconds in an ultrasonic bath is added. The suspension is let stand for 2.5 hours at 42° C., then cooled down in 7 hours at 20° C. The suspension remains at 20° C. for 56 hours. The suspension is not filtrated before analysis. The dimethanol solvate form SB of the hydrochloride salt of 4-methyl-N-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide is obtained.
Quantity
60 mL
Type
reactant
Reaction Step One
Quantity
688.7 μL
Type
reactant
Reaction Step Two
Quantity
2 mL
Type
reactant
Reaction Step Two
Name
Quantity
0.4 mg
Type
reactant
Reaction Step Three
Quantity
40 mg
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
CC1C=C[C:5]([C:6](NC2C=C(C(F)(F)F)C=C(N3C=C(C)N=C3)C=2)=[O:7])=CC=1NC1N=C(C2C=NC=CC=2)C=CN=1.Cl.Cl.[CH3:42][C:43]1[CH:67]=[CH:66][C:46]([C:47]([NH:49][C:50]2[CH:55]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:53]=[C:52]([N:60]3[CH:64]=[C:63]([CH3:65])[N:62]=[CH:61]3)[CH:51]=2)=[O:48])=[CH:45][C:44]=1[NH:68][C:69]1[N:74]=[C:73]([C:75]2[CH:76]=[N:77][CH:78]=[CH:79][CH:80]=2)[CH:72]=[CH:71][N:70]=1.[OH2:81].[CH3:82][OH:83]>>[CH2:6]([O:7][CH2:47][OH:48])[CH2:5][O:81][CH2:82][OH:83].[CH3:42][C:43]1[CH:67]=[CH:66][C:46]([C:47]([NH:49][C:50]2[CH:55]=[C:54]([C:56]([F:57])([F:58])[F:59])[CH:53]=[C:52]([N:60]3[CH:64]=[C:63]([CH3:65])[N:62]=[CH:61]3)[CH:51]=2)=[O:48])=[CH:45][C:44]=1[NH:68][C:69]1[N:74]=[C:73]([C:75]2[CH:76]=[N:77][CH:78]=[CH:79][CH:80]=2)[CH:72]=[CH:71][N:70]=1 |f:2.3|

Inputs

Step One
Name
Quantity
4 g
Type
reactant
Smiles
CC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1
Name
Quantity
60 mL
Type
reactant
Smiles
CO
Step Two
Name
Quantity
688.7 μL
Type
reactant
Smiles
Cl
Name
Quantity
2 mL
Type
reactant
Smiles
CO
Step Three
Name
Quantity
4 mg
Type
reactant
Smiles
Cl.CC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1
Name
Quantity
0.4 mg
Type
reactant
Smiles
O
Name
Quantity
40 mg
Type
reactant
Smiles
CO

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
42 °C
Stirring
Type
CUSTOM
Details
homogenized for 10 seconds in an ultrasonic bath
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
for 60 minutes
Duration
60 min
CUSTOM
Type
CUSTOM
Details
at 50° C
ADDITION
Type
ADDITION
Details
is added
CUSTOM
Type
CUSTOM
Details
for 2.5 hours
Duration
2.5 h
CUSTOM
Type
CUSTOM
Details
at 42° C.
TEMPERATURE
Type
TEMPERATURE
Details
cooled down in 7 hours at 20° C
Duration
7 h
WAIT
Type
WAIT
Details
The suspension remains at 20° C. for 56 hours
Duration
56 h
FILTRATION
Type
FILTRATION
Details
The suspension is not filtrated before analysis

Outcomes

Product
Details
Reaction Time
15 min
Name
Type
product
Smiles
C(COCO)OCO
Name
Type
product
Smiles
Name
Type
product
Smiles
CC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US08829015B2

Procedure details

4.0 g 4-methyl-N-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide free base is dissolved in 60 mL methanol at 50° C. 1.05 equivalent (688.7 μL) of hydrochloric acid is added as a solution in 2 mL of methanol. The solution is let stand for 60 minutes at 50° C. The solution is cooled down to 42° C. and kept at this temperature for 15 minutes. A suspension of 4 mg of 4-methyl-N-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide hydrochloride in methanol (40 mg)/water (0.4 mg) homogenized for 10 seconds in an ultrasonic bath is added. The suspension is let stand for 2.5 hours at 42° C., then cooled down in 7 hours at 20° C. The suspension remains at 20° C. for 56 hours. The suspension is not filtrated before analysis. The dimethanol solvate form SB of the hydrochloride salt of 4-methyl-N-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide is obtained.
Quantity
60 mL
Type
reactant
Reaction Step One
Quantity
688.7 μL
Type
reactant
Reaction Step Two
Quantity
2 mL
Type
reactant
Reaction Step Two
Name
Quantity
0.4 mg
Type
reactant
Reaction Step Three
Quantity
40 mg
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
CC1C=C[C:5]([C:6](NC2C=C(C(F)(F)F)C=C(N3C=C(C)N=C3)C=2)=[O:7])=CC=1NC1N=C(C2C=NC=CC=2)C=CN=1.Cl.Cl.[CH3:42][C:43]1[CH:67]=[CH:66][C:46]([C:47]([NH:49][C:50]2[CH:55]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:53]=[C:52]([N:60]3[CH:64]=[C:63]([CH3:65])[N:62]=[CH:61]3)[CH:51]=2)=[O:48])=[CH:45][C:44]=1[NH:68][C:69]1[N:74]=[C:73]([C:75]2[CH:76]=[N:77][CH:78]=[CH:79][CH:80]=2)[CH:72]=[CH:71][N:70]=1.[OH2:81].[CH3:82][OH:83]>>[CH2:6]([O:7][CH2:47][OH:48])[CH2:5][O:81][CH2:82][OH:83].[CH3:42][C:43]1[CH:67]=[CH:66][C:46]([C:47]([NH:49][C:50]2[CH:55]=[C:54]([C:56]([F:57])([F:58])[F:59])[CH:53]=[C:52]([N:60]3[CH:64]=[C:63]([CH3:65])[N:62]=[CH:61]3)[CH:51]=2)=[O:48])=[CH:45][C:44]=1[NH:68][C:69]1[N:74]=[C:73]([C:75]2[CH:76]=[N:77][CH:78]=[CH:79][CH:80]=2)[CH:72]=[CH:71][N:70]=1 |f:2.3|

Inputs

Step One
Name
Quantity
4 g
Type
reactant
Smiles
CC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1
Name
Quantity
60 mL
Type
reactant
Smiles
CO
Step Two
Name
Quantity
688.7 μL
Type
reactant
Smiles
Cl
Name
Quantity
2 mL
Type
reactant
Smiles
CO
Step Three
Name
Quantity
4 mg
Type
reactant
Smiles
Cl.CC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1
Name
Quantity
0.4 mg
Type
reactant
Smiles
O
Name
Quantity
40 mg
Type
reactant
Smiles
CO

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
42 °C
Stirring
Type
CUSTOM
Details
homogenized for 10 seconds in an ultrasonic bath
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
for 60 minutes
Duration
60 min
CUSTOM
Type
CUSTOM
Details
at 50° C
ADDITION
Type
ADDITION
Details
is added
CUSTOM
Type
CUSTOM
Details
for 2.5 hours
Duration
2.5 h
CUSTOM
Type
CUSTOM
Details
at 42° C.
TEMPERATURE
Type
TEMPERATURE
Details
cooled down in 7 hours at 20° C
Duration
7 h
WAIT
Type
WAIT
Details
The suspension remains at 20° C. for 56 hours
Duration
56 h
FILTRATION
Type
FILTRATION
Details
The suspension is not filtrated before analysis

Outcomes

Product
Details
Reaction Time
15 min
Name
Type
product
Smiles
C(COCO)OCO
Name
Type
product
Smiles
Name
Type
product
Smiles
CC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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