![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](/img/structure/B1429255.png)
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
Peso molecular: 615.4 g/mol
Clave InChI: VUCVSBZRQBGJPT-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US08835443B2
Procedure details
To p-toluenesulfonic acid 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-yl ester 77 (28.0 g) and 3′-aminoacetanilide 57 (13.2 g) were added N,N-dimethylacetamide (84.0 ml) and 2,6-lutidine (15.3 ml), and the mixture was stirred at 130° C. for 4 hrs. After allowing to cool with stirring, methanol (196 ml) was added dropwise, and the mixture was stirred at room temperature. The crystals were collected by filtration and dried to give 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 58 (25.2 g, yield 93%) as colorless crystals.
Quantity
28 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11](OS(C4C=CC(C)=CC=4)(=O)=O)=[C:12]([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:29]3[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=3[F:36])[C:5]2=[O:37])[CH2:3][CH2:2]1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=1)[NH:42][C:43](=[O:45])[CH3:44].CN(C)C(=O)C.N1C(C)=CC=CC=1C>CO>[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11]([NH:38][C:39]4[CH:40]=[C:41]([NH:42][C:43](=[O:45])[CH3:44])[CH:46]=[CH:47][CH:48]=4)=[C:12]([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:29]3[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=3[F:36])[C:5]2=[O:37])[CH2:2][CH2:3]1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
28 g
|
|
Type
|
reactant
|
|
Smiles
|
C1(CC1)N1C(N(C2=C(C1=O)C(=C(C(N2C)=O)C)OS(=O)(=O)C2=CC=C(C=C2)C)C2=C(C=C(C=C2)I)F)=O
|
|
Name
|
|
|
Quantity
|
13.2 g
|
|
Type
|
reactant
|
|
Smiles
|
NC=1C=C(NC(C)=O)C=CC1
|
|
Name
|
|
|
Quantity
|
84 mL
|
|
Type
|
reactant
|
|
Smiles
|
CN(C(C)=O)C
|
|
Name
|
|
|
Quantity
|
15.3 mL
|
|
Type
|
reactant
|
|
Smiles
|
N1=C(C=CC=C1C)C
|
Step Two
|
Name
|
|
|
Quantity
|
196 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
130 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the mixture was stirred at 130° C. for 4 hrs
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to cool
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
with stirring
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
the mixture was stirred at room temperature
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The crystals were collected by filtration
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
Details
Reaction Time |
4 h |
|
Name
|
|
|
Type
|
product
|
|
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
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 25.2 g | |
| YIELD: PERCENTYIELD | 93% | |
| YIELD: CALCULATEDPERCENTYIELD | 93.2% |
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. |
