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[ CAS No. 827022-32-2 ] {[proInfo.proName]}

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Chemical Structure| 827022-32-2
Chemical Structure| 827022-32-2
Structure of 827022-32-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 827022-32-2 ]

CAS No. :827022-32-2 MDL No. :
Formula : C24H30ClN7O2 Boiling Point : -
Linear Structure Formula :- InChI Key :STEQOHNDWONVIF-UHFFFAOYSA-N
M.W : 483.99 Pubchem ID :11431660
Synonyms :
PD 0332991 monohydrochloride;PD 0332991 (hydrochloride);Palbociclib;Palbociclib HCl

Calculated chemistry of [ 827022-32-2 ]

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.46
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 143.0
TPSA : 105.04 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.62
Log Po/w (WLOGP) : 3.01
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 2.51
Consensus Log Po/w : 1.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.51
Solubility : 0.015 mg/ml ; 0.0000309 mol/l
Class : Moderately soluble
Log S (Ali) : -4.48
Solubility : 0.0162 mg/ml ; 0.0000334 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.49
Solubility : 0.000157 mg/ml ; 0.000000324 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.65

Safety of [ 827022-32-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 827022-32-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 827022-32-2 ]
  • Downstream synthetic route of [ 827022-32-2 ]

[ 827022-32-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 571189-10-1 ]
  • [ 827022-32-2 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride In dichloromethane at 0 - 20℃; EXAMPLE 3 Preparation of 6-ACETVL-8-CVCLOPENTVI-5-METHYL-2- (5-PIPERAZIN-1- EL-PVRIDIN-2-YLAMINO)- 8H-PVRIDOR2, 3-DLPYRIMIDIN-7-ONE HVDROCHLORIDE 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] idin-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 percent).
92% With hydrogenchloride In dichloromethane at 20℃; Comparative Example 1C: Preparation of ψ-acetyl-δ-cyclopentyl-S-methyl^-tS-piperazin-i-yl-pyridin^- ylamino)-8H-pyrido[2,3-c/]pyrimidin-7-one hydrochloride; Hydrogen chloride gas was bubbled into an ice-bath cooled solution of 4-{6-[8-cyclopentyl-6-(1-ethoxy- vinyO-S-methyl-Z-oxo-Z.β-dihydro-pyridop.S-c/lpyrimidin-Z-ylaminol-pyridin-S-ylJ-piperazine-i-carboxylic acid tert-butyl ester (4.50 g, 0.00783 mol, prepared as in 2005-0059670A1 ) 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)-8/-/-pyrido[2,3-d]pyrimidin-7-one as a yellow solid (4.01 g, 92 percent). Melting point 2000C. HPLC, C18 reverse phase, 10 percent-95 percent gradient of 0.1 percentTFA/CH3CN in 0.1 percent TFA/H2O during 22 minutes: 99.0 percent at 11.04 minutes. MS (APCI) M+ +1 : calc'd, 448.2, found, 448.3. Anal, calc'd for C24H29N7O2-2.4 H2CM .85 HCI: C, 51.64; H, 6.44; N, 17.56, Cl (total), 11.75. Found: C, 51.31 ; H, 6.41 ; N1 17.20; Cl (total), 12.11.
Reference: [1] Patent: WO2005/5426, 2005, A1, . Location in patent: Page/Page column 22
[2] Patent: US2003/149001, 2003, A1,
[3] Patent: WO2008/32157, 2008, A2, . Location in patent: Page/Page column 24-25
  • 2
  • [ 571190-30-2 ]
  • [ 827022-32-2 ]
YieldReaction ConditionsOperation in experiment
90.8% With hydrogenchloride In ethanol; water at 20℃; for 93 h; Heating 1.5 g (3.35 mmol) palbociclib base and 30 ml ethanol are measured into a device providing intensive stirring, then during boiling 3.18 ml (3.18 mmol) of a 1 M hydrochloric acid solution is added to it drop by drop. The solution is cooled to room temperature, mixed for 93 hours, then this crystalline product is filtered, washed with a small amount of cold ethanol and then MTBE, then dried in the air.Yield: 0.62 g (90.8percent)Mp.: 288—290°CAnalysis with respect to the chemical formula C24H30C1N702 (484.00):Calculated C: 59.56 percent H: 6.25 percent N: 20.26 percent Cl: 7.32 percent. Measured C: 59.40 percent H: 6.26 percent N: 20.00 percent Cl: 7.30 percent. 1H-NMR (DMSO-d6, 400 MHz): 10.21 (bs, 1H), 9.27 (b, 2H), 8.97 (s, 1H), 8.12 (d, 1=2.9 Hz, 1H), 7.92 (d, 1=9.0 Hz, 1H), 7.54 (dd, 11=2.9 Hz, 12=9.1 Hz, 1H), 5.83 (m, 1H), 3.40 (m, 4H),32.25 (m, 4H), 2.43 (s, 3H), 2.32 (s, 3H), 2.24 (m, 2H), 1.89 (m, 2H), 1.78 (m, 2H), 1.59 (m, 2H). 13C-NMR (DMSO-d6, 125 MHz): 202.52, 160.87, 158.62, 158.37, 154.90, 145.45, 142.48,142.16, 136.28, 129.53, 125.73, 115.11, 106.86, 53.11, 45.76, 42.61, 31.42, 27.70, 25.25,13.76.
Reference: [1] Patent: WO2017/72543, 2017, A1, . Location in patent: Page/Page column 44
  • 3
  • [ 571188-82-4 ]
  • [ 827022-32-2 ]
Reference: [1] Patent: CN105924439, 2016, A,
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[ 827022-32-2 ]

Chemical Structure| 571190-30-2

A295334[ 571190-30-2 ]

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

Reason: Free-salt