Synthesis routes 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-{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

Katalognummer B8676315

Molekulargewicht: 575.7 g/mol

InChI-Schlüssel: ZSUHBFDUYDVOFZ-UHFFFAOYSA-N

Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.

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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.

Name

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

Quantity

4.5 g

Type

reactant

Reaction Step One

Name

DCM

Quantity

100 mL

Type

solvent

Reaction Step One

Name

diethyl ether

Quantity

200 mL

Type

solvent

Reaction Step Two

[Compound]

Name

hydrochloride salt

Name

6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

Yield

92%

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	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
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	DCM
Quantity	100 mL
Type	solvent
Smiles	C(Cl)Cl

Step Two

Name	diethyl ether
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

[Compound]

Name	hydrochloride salt
Type	product
Smiles

Name	6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one
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

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.