Welcome to the BenchChem Online Store!
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.
In Stock
  • Click on QUICK INQUIRY to receive a quote from our team of experts.
  • With the quality product at a COMPETITIVE price, you can focus more on your research.
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
13.2 g
Type
reactant
Reaction Step One
Quantity
84 mL
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.
© Copyright 2024 BenchChem. All Rights Reserved.