tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate CAS#: 866084-31-3; ChemWhat Code: 1257845

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Nametert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate
IUPAC Nametert-butyl 4-[6-[[6-(1-butoxyethenyl)-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylate  
Molecular Structuretert-butyl-4-6-8-cyclopentyl-5-Methyl-7-oxo-6-1-propoxyvinyl-78-dihydropyrido23-dpyriMidin-2-ylaMinopyridin-3-ylpiperazine-1-carboxylate-CAS-866084-31-3
CAS Registry Number 866084-31-3
MDL NumberMFCD18642713
Synonyms866084-31-3
tert-butyl 4-(6-((6-(1-butoxyvinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate
4-[6-[[6-(1-Butoxyvinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylic acid tert-butyl ester
tert-butyl 4-[6-[[6-(1-butoxyethenyl)-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylate
4-[6-[6-(1-butoxy-vinyl)-8-cyclopentyl-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-[6-(1-butoxy-vinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester
tert-Butyl 4-[6-[[6-(1-Butoxyethenyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl]amino]-pyridin-3-yl]-piperazine-1-carboxylate
MFCD28978558
SCHEMBL2076205
SCWKOLRZBMGTNT-UHFFFAOYSA-N
BCP15574
CS-M0541
AKOS025293472
CS-W004355
AC-33717
DS-19152
DB-120225
C11197
tert-butyl4-(6-((6-(1-butoxyvinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate
Molecular FormulaC33H45N7O4
Molecular Weight603.8
InChIInChI=1S/C33H45N7O4/c1-7-8-19-43-23(3)28-22(2)26-21-35-31(37-29(26)40(30(28)41)24-11-9-10-12-24)36-27-14-13-25(20-34-27)38-15-17-39(18-16-38)32(42)44-33(4,5)6/h13-14,20-21,24H,3,7-12,15-19H2,1-2,4-6H3,(H,34,35,36,37)
InChI KeySCWKOLRZBMGTNT-UHFFFAOYSA-N
Isomeric SMILESCCCCOC(=C)C1=C(C2=CN=C(N=C2N(C1=O)C3CCCC3)NC4=NC=C(C=C4)N5CCN(CC5)C(=O)OC(C)(C)C)C
Patent Information
Patent IDTitlePublication Date
WO2008/32157SYNTHESIS OF 2-(PYRIDIN-2-YLAMINO)-PYRIDO[2,3-D]PYRIMIDIN-7-ONES2008

Physical Data

AppearanceLight yellow to brown powder

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts1Hdimethylsulfoxide-d6
Chemical shifts13Cdimethylsulfoxide-d6
Chemical shifts1H
Chemical shifts1Hdimethylsulfoxide-d6500
Chemical shifts13Cdimethylsulfoxide-d6126
Chemical shifts1Hchloroform-d1300

Route of Synthesis (ROS)

Route of Synthesis (ROS) of tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate CAS 866084-31-3
Route of Synthesis (ROS) of tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate CAS 866084-31-3Route of Synthesis (ROS) of tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate CAS 866084-31-3
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In N,N-dimethyl-formamide at 80 – 85℃; for 8h; Time; Heck Reaction;

Experimental Procedure
step 1: A mixture of 4-[6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyridino[2,3-d]pyridine-2-yl-amino)-pyridine-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (9.8 g, 0.017 mol), DMF (140 ml), vinyl n-butyl ether (17 g,0.17 mol), K2CO3 (5.27 g, 0.041 mol), Pd2dba3 (1.6 g, 0.17 mmol) and DABCO (0.23 g, 2.04 mmol) were added to the reaction flask, Heated to 80 ~ 85 reaction 8h, The reaction was terminated by TLC, Cooling to 35 deg C, filter, After adding 120 ml of purified water, Crystallization, Filtration, 60 deg C vacuum drying 8h, To give 4-[6-[[6-(1-Butoxyvinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylic acid tert-butyl ester (9.7 g, Yield 96%).		96%
With palladium diacetate; N-ethyl-N,N-diisopropylamine; DPEPhos In methanol; butan-1-ol at 40 – 60℃; for 3h; Temperature; Inert atmosphere;

Experimental Procedure
1 Preparation of a solid form of compound of formula (2)
100 g of compound of formula (3) was suspended in 375 g of dry 1 -butanol and 625 g of dry methanol at 40°C. The suspension was placed under nitrogen and 50 g of compound of formula (4), 50 g of diisopropylethylamine, 1 g of Pd(OAc)2 and 3 g of DPEPhos were added. The reaction mixture was heated at 60°C and stirred at this temperature for 3 hours. (0082) The mixture was filtered, to the fitrate 250 g of methanol and 300 g of water during 40 minutes were added. The suspension was cooled to 0-5°C, solid compound (2) was filtered off and washed with a mixture of 240 g of methanol and 40 g of water. The fitrer cake was dried at 65°C. 94 g of compound of formula (2) was obtained (yield 90% of the theoretical yield) in HPLC purity 99.1%. XRPD pattern of the obtained solid corresponds to XRPD pattern depicted in Figure 1. The content of palladium in obtained solid was 25 ppm.		90%
With dichloro(1,1′-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-ethyl-N,N-diisopropylamine In butan-1-ol at 95 – 100℃; Inert atmosphere;

Experimental Procedure
Replace the reaction flask with nitrogen, add 1580ml (10V) n-butanol, bubble with nitrogen, add 158g intermediate I, add 108.2g vinyl n-butyl ether, 69.9g N,N-diisopropylethylamine, 7.7g Pd (dppf) Cl2·DCM, nitrogen replacement 3 times, maintaining a slight nitrogen flow, heating to 95-100°C, under nitrogen protection, keeping temperature and stirring, HPLC detection, extraction, concentration under reduced pressure, recrystallization, and drying to obtain the intermediate II 135g, yield 89%.		89%

Safety and Hazards

GHS Hazard StatementsNot Classified

Other Data

Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
Molecular Weight603.765
logP6.142
HBA11
HBD1
Matching Lipinski Rules1
Veber rules component
Polar Surface Area (PSA)113.02
Rotatable Bond (RotB)12
Matching Veber Rules1
Use Pattern
Tert-butyl 4-(6-(8-cyclopentyl-5-methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)pyridin-3-yl)piperazine-1-carboxylate is a complex pharmaceutical intermediate commonly used in the development and synthesis of anti-cancer drugs. The compound’s structure, which includes multiple cyclic and heterocyclic rings, allows it to target specific enzymes or proteins, making it an essential precursor in certain targeted cancer therapies. Specifically, this compound may work by affecting DNA synthesis or protein phosphorylation pathways in tumor cells, thereby inhibiting cancer cell proliferation.

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