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molecular formula C26H23FIN5O4 B1429255 N-(3-(3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino)phenyl)acetamide CAS No. 871700-25-3

N-(3-(3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino)phenyl)acetamide

Cat. No. B1429255
M. Wt: 615.4 g/mol
InChI Key: VUCVSBZRQBGJPT-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US09181243B2

Procedure details

Under a nitrogen atmosphere, tetrahydrofuran (40 mL) was added to N-{3-[3-cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-ylamino]-phenyl}-acetamide (5 g) and a methanol solution (1.57 g) containing 28% sodium methoxide was added and the mixture was stirred at room temperature for 4 hours. Acetic acid (0.56 mL) was added to the mixture and the mixture was stirred at room temperature for 30 min. And then water (40 mL) was added and the mixture was further stirred for 1 hour. The crystals were collected by filtration and dried under reduced pressure at 40° C. to give trametinib (4.75 g). Its HPLC content of A impurity is 0.42 wt %.
Quantity
40 mL
Type
reactant
Reaction Step One
Quantity
1.57 g
Type
reactant
Reaction Step Two
Name
sodium methoxide
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
40 mL
Type
solvent
Reaction Step Three
Quantity
0.56 mL
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
O1CCCC1.[CH:6]1([N:9]2[C:14](=[O:15])[C:13]3[C:16]([NH:23][C:24]4[CH:25]=[C:26]([NH:30][C:31](=[O:33])[CH3:32])[CH:27]=[CH:28][CH:29]=4)=[C:17]([CH3:22])[C:18](=[O:21])[N:19]([CH3:20])[C:12]=3[N:11]([C:34]3[CH:39]=[CH:38][C:37]([I:40])=[CH:36][C:35]=3[F:41])[C:10]2=[O:42])[CH2:8][CH2:7]1.CO.C[O-].[Na+]>O.C(O)(=O)C>[CH3:22][C:17]1[C:18](=[O:21])[N:19]([CH3:20])[C:12]([NH:11][C:34]2[CH:39]=[CH:38][C:37]([I:40])=[CH:36][C:35]=2[F:41])=[C:13]2[C:14]([N:9]([CH:6]3[CH2:8][CH2:7]3)[C:10]([N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([CH3:32])=[O:33])[CH:25]=3)[C:16]=12)=[O:42])=[O:15] |f:3.4|

Inputs

Step One
Name
Quantity
40 mL
Type
reactant
Smiles
O1CCCC1
Name
Quantity
5 g
Type
reactant
Smiles
C1(CC1)N1C(N(C2=C(C1=O)C(=C(C(N2C)=O)C)NC=2C=C(C=CC2)NC(C)=O)C2=C(C=C(C=C2)I)F)=O
Step Two
Name
Quantity
1.57 g
Type
reactant
Smiles
CO
Name
sodium methoxide
Quantity
0 (± 1) mol
Type
reactant
Smiles
C[O-].[Na+]
Step Three
Name
Quantity
40 mL
Type
solvent
Smiles
O
Step Four
Name
Quantity
0.56 mL
Type
solvent
Smiles
C(C)(=O)O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
the mixture was stirred at room temperature for 4 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added
STIRRING
Type
STIRRING
Details
the mixture was stirred at room temperature for 30 min
Duration
30 min
STIRRING
Type
STIRRING
Details
the mixture was further stirred for 1 hour
Duration
1 h
FILTRATION
Type
FILTRATION
Details
The crystals were collected by filtration
CUSTOM
Type
CUSTOM
Details
dried under reduced pressure at 40° C.

Outcomes

Product
Details
Reaction Time
4 h
Name
Type
product
Smiles
CC1=C2C(=C(N(C1=O)C)NC=3C=CC(=CC3F)I)C(=O)N(C(=O)N2C=4C=CC=C(C4)NC(=O)C)C5CC5
Measurements
Type Value Analysis
AMOUNT: MASS 4.75 g
YIELD: CALCULATEDPERCENTYIELD 95%

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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