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molecular formula C28H22F3N7O B1678881 Nilotinib CAS No. 641571-10-0

Nilotinib

Cat. No. B1678881
M. Wt: 529.5 g/mol
InChI Key: HHZIURLSWUIHRB-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08937082B2

Procedure details

To a 1 liter reactor was fed 40 g of 4-methyl-3-(4-(pyridine-3-yl)pyrimidin-2-ylamino)benzoic acid (0.13 mol), 200 ml of N-methylpyrrolidone (NMP) (5V) and 13 ml of thionyl chloride (0.18 mol). The reactor was heated to 60° C. and maintained at 60° C. for 1.5 hr. After 1.5 hr of heating, 31.5 g of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazol-1-yl)benzenamine (0.13 mol) was fed into the reactor. The reactor was then heated to 90° C., and maintained for 30 minutes at this temperature. Then 200 ml (5V) of water was added. The resulting mixture was maintained for 2 hours at 90° C. Then, an additional 240 ml (6V) of N-methylpyrrolidone was added, followed by 26.5 ml of sodium hydroxide (47% aqueous) to raise the pH to 6.5-7. The reactor was then cooled to 40° C. and maintained for 3 hours. The mixture was then filtered and the filter cake was washed with ethanol and water. The washed material was then dried in a vacuum tray oven overnight to provide dry Nilotinib base (62.1 g, Yield 90%)
Quantity
40 g
Type
reactant
Reaction Step One
Quantity
13 mL
Type
reactant
Reaction Step Two
Quantity
31.5 g
Type
reactant
Reaction Step Three
Quantity
26.5 mL
Type
reactant
Reaction Step Four
Quantity
240 mL
Type
solvent
Reaction Step Five
Name
Quantity
200 mL
Type
solvent
Reaction Step Six
Quantity
200 mL
Type
solvent
Reaction Step Seven
Yield
90%

Identifiers

REACTION_CXSMILES
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[NH:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:14][N:13]=1.S(Cl)(Cl)=O.[F:28][C:29]([F:44])([F:43])[C:30]1[CH:31]=[C:32]([NH2:42])[CH:33]=[C:34]([N:36]2[CH:40]=[C:39]([CH3:41])[N:38]=[CH:37]2)[CH:35]=1.[OH-].[Na+]>CN1CCCC1=O>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:42][C:32]2[CH:31]=[C:30]([C:29]([F:44])([F:43])[F:28])[CH:35]=[C:34]([N:36]3[CH:37]=[N:38][C:39]([CH3:41])=[CH:40]3)[CH:33]=2)=[O:8])=[CH:4][C:3]=1[NH:11][C:12]1[N:13]=[CH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=2)[N:17]=1 |f:3.4|

Inputs

Step One
Name
Quantity
40 g
Type
reactant
Smiles
CC1=C(C=C(C(=O)O)C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1
Step Two
Name
Quantity
13 mL
Type
reactant
Smiles
S(=O)(Cl)Cl
Step Three
Name
Quantity
31.5 g
Type
reactant
Smiles
FC(C=1C=C(C=C(C1)N1C=NC(=C1)C)N)(F)F
Step Four
Name
Quantity
26.5 mL
Type
reactant
Smiles
[OH-].[Na+]
Step Five
Name
Quantity
240 mL
Type
solvent
Smiles
CN1C(CCC1)=O
Step Six
Name
Quantity
200 mL
Type
solvent
Smiles
CN1C(CCC1)=O
Step Seven
Name
Quantity
200 mL
Type
solvent
Smiles
CN1C(CCC1)=O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
60 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
To a 1 liter reactor was fed
TEMPERATURE
Type
TEMPERATURE
Details
maintained at 60° C. for 1.5 hr
Duration
1.5 h
TEMPERATURE
Type
TEMPERATURE
Details
After 1.5 hr of heating
Duration
1.5 h
TEMPERATURE
Type
TEMPERATURE
Details
The reactor was then heated to 90° C.
TEMPERATURE
Type
TEMPERATURE
Details
maintained for 30 minutes at this temperature
Duration
30 min
TEMPERATURE
Type
TEMPERATURE
Details
The resulting mixture was maintained for 2 hours at 90° C
Duration
2 h
TEMPERATURE
Type
TEMPERATURE
Details
to raise the pH to 6.5-7
TEMPERATURE
Type
TEMPERATURE
Details
The reactor was then cooled to 40° C.
TEMPERATURE
Type
TEMPERATURE
Details
maintained for 3 hours
Duration
3 h
FILTRATION
Type
FILTRATION
Details
The mixture was then filtered
WASH
Type
WASH
Details
the filter cake was washed with ethanol and water
CUSTOM
Type
CUSTOM
Details
The washed material was then dried in a vacuum tray oven overnight
Duration
8 (± 8) h

Outcomes

Product
Name
Type
product
Smiles
CC=1C=CC(=CC1NC=2N=CC=C(N2)C=3C=CC=NC3)C(=O)NC=4C=C(C=C(C4)N5C=C(N=C5)C)C(F)(F)F
Measurements
Type Value Analysis
AMOUNT: MASS 62.1 g
YIELD: PERCENTYIELD 90%
YIELD: CALCULATEDPERCENTYIELD 90.2%

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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