![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
货号 B1429255
分子量: 615.4 g/mol
InChI 键: VUCVSBZRQBGJPT-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
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
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REACTION_CXSMILES
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[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
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Inputs
Step One
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Name
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|
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Quantity
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28 g
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|
Type
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reactant
|
|
Smiles
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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
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Name
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|
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Quantity
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13.2 g
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Type
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reactant
|
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Smiles
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NC=1C=C(NC(C)=O)C=CC1
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Name
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|
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Quantity
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84 mL
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|
Type
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reactant
|
|
Smiles
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CN(C(C)=O)C
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|
Name
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|
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Quantity
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15.3 mL
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|
Type
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reactant
|
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Smiles
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N1=C(C=CC=C1C)C
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Step Two
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Name
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|
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Quantity
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196 mL
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Type
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solvent
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Smiles
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CO
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Conditions
Temperature
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Control Type
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UNSPECIFIED
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Setpoint
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130 °C
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Stirring
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Type
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CUSTOM
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Details
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the mixture was stirred at 130° C. for 4 hrs
|
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Rate
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UNSPECIFIED
|
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RPM
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0
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Other
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Conditions are dynamic
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1
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Details
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See reaction.notes.procedure_details.
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Workups
TEMPERATURE
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Type
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TEMPERATURE
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Details
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to cool
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STIRRING
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Type
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STIRRING
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Details
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with stirring
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STIRRING
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Type
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STIRRING
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Details
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the mixture was stirred at room temperature
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FILTRATION
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Type
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FILTRATION
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Details
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The crystals were collected by filtration
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CUSTOM
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Type
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CUSTOM
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|
Details
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dried
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Outcomes
Product
Details
Reaction Time |
4 h |
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Name
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|
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Type
|
product
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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
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Source
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Open Reaction Database (ORD) |
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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. |
