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molecular formula C31H41N7O4 B8676315 4-{6-[8-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester

4-{6-[8-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester

Cat. No. B8676315
M. Wt: 575.7 g/mol
InChI Key: ZSUHBFDUYDVOFZ-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07863278B2

Procedure details

Hydrogen chloride gas was bubbled into an ice-bath cooled solution of 4-{6-[8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester (4.50 g, 0.00783 mol, prepared as in Example 2) in DCM (100 mL). The resulting suspension was stoppered and stirred at RT overnight, then diluted with diethyl ether (200 mL). The solid was collected by filtration, washed with diethyl ether, and dried to give the hydrochloride salt of 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid (4.01 g, 92%). Melting point 200° C. HPLC, C18 reverse phase, 10%-95% gradient of 0.1% TFA/CH3CN in 0.1% TFA/H2O during 22 minutes: 99.0% at 11.04 minutes. MS (APCl) M++1: calc'd, 448.2, found, 448.3. Anal. calc'd for C24H29N7O2.2.4 H2O.1.85 HCl: C, 51.64; H, 6.44; N, 17.56, Cl (total), 11.75. Found: C, 51.31; H, 6.41; N, 17.20; Cl (total), 12.11.

Identifiers

REACTION_CXSMILES
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:30]([CH3:31])=[C:29]([C:32]([O:34]CC)=[CH2:33])[C:28](=[O:37])[N:27]([CH:38]5[CH2:42][CH2:41][CH2:40][CH2:39]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(OCC)C>[C:32]([C:29]1[C:28](=[O:37])[N:27]([CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[C:25]2[N:26]=[C:21]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[CH:15][N:16]=3)[N:22]=[CH:23][C:24]=2[C:30]=1[CH3:31])(=[O:34])[CH3:33]

Inputs

Step One
Name
Quantity
4.5 g
Type
reactant
Smiles
C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C=NC(=CC1)NC=1N=CC2=C(N1)N(C(C(=C2C)C(=C)OCC)=O)C2CCCC2
Name
Quantity
100 mL
Type
solvent
Smiles
C(Cl)Cl
Step Two
Name
Quantity
200 mL
Type
solvent
Smiles
C(C)OCC

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred at RT overnight
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
Hydrogen chloride gas was bubbled into an ice-bath
FILTRATION
Type
FILTRATION
Details
The solid was collected by filtration
WASH
Type
WASH
Details
washed with diethyl ether
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
8 (± 8) h
Name
Type
product
Smiles
Name
Type
product
Smiles
C(C)(=O)C1=C(C2=C(N=C(N=C2)NC2=NC=C(C=C2)N2CCNCC2)N(C1=O)C1CCCC1)C
Measurements
Type Value Analysis
AMOUNT: MASS 4.01 g
YIELD: PERCENTYIELD 92%
YIELD: CALCULATEDPERCENTYIELD 114.4%

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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