Synthesis routes of 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

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

Número de catálogo B1429255

: 871700-25-3

Peso molecular: 615.4 g/mol

Clave InChI: VUCVSBZRQBGJPT-UHFFFAOYSA-N

Atención: Solo para uso de investigación. No para uso humano o veterinario.

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Patent

US08835443B2

Procedure details

Under a nitrogen atmosphere, to a solution (1.57 g) of 28% sodium methoxide in methanol was added tetrahydrofuran (40 ml), N-{3-[3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-ylamino]phenyl}acetamide 58 (5.00 g) obtained in Step 7 was added, and the mixture was stirred at room temperature for 4 hrs. Acetic acid (0.56 ml) was added, and the mixture was stirred at room temperature for 30 min. Water (40 ml) was added and the mixture was further stirred for 1 hr. The crystals were collected by filtration and dried to give N-{3-[3-cyclopropyl-5-(2-fluoro-4-iodophenylamino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydro-2H-pyrido[4,3-d]pyrimidin-1-yl]phenyl}acetamide 59 (4.75 g, yield 95%) as colorless crystals.

Name

sodium methoxide

Quantity

1.57 g

Type

reactant

Reaction Step One

Name

tetrahydrofuran

Quantity

40 mL

Type

reactant

Reaction Step One

Name

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

Quantity

5 g

Type

reactant

Reaction Step One

Name

methanol

Quantity

0 (± 1) mol

Type

solvent

Reaction Step One

Name

Acetic acid

Quantity

0.56 mL

Type

reactant

Reaction Step Two

Name

Water

Quantity

40 mL

Type

solvent

Reaction Step Three

Name

N-{3-[3-cyclopropyl-5-(2-fluoro-4-iodophenylamino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydro-2H-pyrido[4,3-d]pyrimidin-1-yl]phenyl}acetamide

Yield

95%

Identifiers

REACTION_CXSMILES

C[O-].[Na+].O1CCCC1.[CH:9]1([N:12]2[C:17](=[O:18])[C:16]3[C:19]([NH:26][C:27]4[CH:28]=[C:29]([NH:33][C:34](=[O:36])[CH3:35])[CH:30]=[CH:31][CH:32]=4)=[C:20]([CH3:25])[C:21](=[O:24])[N:22]([CH3:23])[C:15]=3[N:14]([C:37]3[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:38]=3[F:44])[C:13]2=[O:45])[CH2:11][CH2:10]1.C(O)(=O)C>CO.O>[CH:9]1([N:12]2[C:17](=[O:18])[C:16]3=[C:15]([NH:14][C:37]4[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:38]=4[F:44])[N:22]([CH3:23])[C:21](=[O:24])[C:20]([CH3:25])=[C:19]3[N:26]([C:27]3[CH:28]=[C:29]([NH:33][C:34](=[O:36])[CH3:35])[CH:30]=[CH:31][CH:32]=3)[C:13]2=[O:45])[CH2:11][CH2:10]1 |f:0.1|

Inputs

Step One

Name	sodium methoxide
Quantity	1.57 g
Type	reactant
Smiles	C[O-].[Na+]

Name	tetrahydrofuran
Quantity	40 mL
Type	reactant
Smiles	O1CCCC1

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

Name	methanol
Quantity	0 (± 1) mol
Type	solvent
Smiles	CO

Step Two

Name	Acetic acid
Quantity	0.56 mL
Type	reactant
Smiles	C(C)(=O)O

Step Three

Name	Water
Quantity	40 mL
Type	solvent
Smiles	O

Conditions

Temperature

Control Type

AMBIENT

Stirring

Type	CUSTOM
Details	the mixture was stirred at room temperature for 4 hrs
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 hr
Duration	1 h

FILTRATION

Type	FILTRATION
Details	The crystals were collected by filtration

CUSTOM

Type	CUSTOM
Details	dried

Outcomes

Product

Details

Reaction Time

4 h

Name	N-{3-[3-cyclopropyl-5-(2-fluoro-4-iodophenylamino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydro-2H-pyrido[4,3-d]pyrimidin-1-yl]phenyl}acetamide
Type	product
Smiles	C1(CC1)N1C(N(C=2C(C1=O)=C(N(C(C2C)=O)C)NC2=C(C=C(C=C2)I)F)C=2C=C(C=CC2)NC(C)=O)=O

Measurements

Type	Value	Analysis
AMOUNT: MASS	4.75 g
YIELD: PERCENTYIELD	95%
YIELD: CALCULATEDPERCENTYIELD	95%

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.