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[ CAS No. 142217-81-0 ] {[proInfo.proName]}

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Chemical Structure| 142217-81-0
Chemical Structure| 142217-81-0
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Product Details of [ 142217-81-0 ]

CAS No. :142217-81-0 MDL No. :MFCD11977291
Formula : C26H27N5O3 Boiling Point : -
Linear Structure Formula :- InChI Key :KROVOOOAPHSWCR-FKBYEOEOSA-N
M.W : 457.52 Pubchem ID :135565404
Synonyms :

Calculated chemistry of [ 142217-81-0 ]

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 21
Fraction Csp3 : 0.27
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 130.83
TPSA : 108.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.8
Log Po/w (XLOGP3) : 2.22
Log Po/w (WLOGP) : 3.33
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 3.46
Consensus Log Po/w : 2.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.0
Solubility : 0.0453 mg/ml ; 0.000099 mol/l
Class : Moderately soluble
Log S (Ali) : -4.12
Solubility : 0.0344 mg/ml ; 0.0000752 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.57
Solubility : 0.0000123 mg/ml ; 0.000000027 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.59

Safety of [ 142217-81-0 ]

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 [ 142217-81-0 ]

* 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.

  • Downstream synthetic route of [ 142217-81-0 ]

[ 142217-81-0 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 142217-80-9 ]
  • [ 142217-81-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; methanol; ethanol; chloroform; J. [1S-(1alpha,3alpha,4beta)]-2-Amino-1,9-dihydro-9-[2-methylene-4-(phenylmethoxy)-3-[(phenyl-methoxy)methyl]cyclopentyl]-6H-purin-6-one A mixture of crude [1S-(1alpha,3alpha,4beta)]-N-[(4-methoxyphenyl)diphenylmethyl]-6-(phenylmethoxy)-9-[2-methylene-4-(phenylmethoxy)-3-[(phenylmethoxy)-methyl]cyclopentyl]-9H-purin-2-amine (2.5 g), tetrahydrofuran (25 ml), methanol (25 ml) and 3N hydrochloric acid (12.5 ml) was heated at 50 for 2.5 hours and cooled to room temperature. The pH was adjusted to 7.3 with 1N potassium hydroxide, and the mixture was extracted with ethyl acetate (3*120 ml). The ethyl acetate extract was dried (sodium sulfate) and concentrated in vacuo to a residue, which was applied to a column of Merck silica gel (340 ml) packed in 3% ethanol in chloroform. Elution with a gradient of 3-20% ethanol in chloroform gave 316 mg of desired product as a residue.
  • 2
  • [ 142217-81-0 ]
  • [ 142217-69-4 ]
YieldReaction ConditionsOperation in experiment
73% To a solution of the product of step lk (25 <strong>[142217-81-0]m</strong>g, 0.059 <strong>[142217-81-0]m</strong><strong>[142217-81-0]m</strong>ol) in dichloro<strong>[142217-81-0]m</strong>ethane (1 <strong>[142217-81-0]m</strong>l) at -78 C was added a solution of boron trichloride in dichloro<strong>[142217-81-0]m</strong>ethane (0.3 <strong>[142217-81-0]m</strong>L, 1 M), stirred at -20 C for 30<strong>[142217-81-0]m</strong>in, and <strong>[142217-81-0]m</strong>ethanol (l<strong>[142217-81-0]m</strong>L) was added to quench the reaction. After all the volatiles were re<strong>[142217-81-0]m</strong>oved by nitrogen flow, the residue was dissolved in water and the aqueous phase was extracted with ether and then neutralized with aqueous sodiu<strong>[142217-81-0]m</strong> hydroxide (1 M). After distilling off half of the water, the resulting white suspension was collected by filtration and dried to yield 11<strong>[142217-81-0]m</strong>g of a white solid in 73%
72% With boron trihalide; In dichloromethane; at -60 - -10℃; for 1.5h;Large scale; Boron trifluoride in dichloro<strong>[142217-81-0]m</strong>ethane (1 M, 10 kg, 20.8 <strong>[142217-81-0]m</strong>ol) was added dropwise to asolution of co<strong>[142217-81-0]m</strong>pound 10 (594 g, 1.2 <strong>[142217-81-0]m</strong>ol) and anhydrous dichloro<strong>[142217-81-0]m</strong>ethane (12 kg) at60C. After addition, the <strong>[142217-81-0]m</strong>ixture was stirred at 60C for 30 <strong>[142217-81-0]m</strong>in. The <strong>[142217-81-0]m</strong>ixture wasthen stirred for 1 h at 20 C10C. After cooling to 60C, <strong>[142217-81-0]m</strong>ethanol (15 kg) wasadded dropwise. The <strong>[142217-81-0]m</strong>ethanol was re<strong>[142217-81-0]m</strong>oved under reduced pressure. The residue was dissolvedin water. The solution was washed two ti<strong>[142217-81-0]m</strong>es with ethyl acetate. 2 M sodiu<strong>[142217-81-0]m</strong>hydroxide aqueous solution was added to pH 7. The precipitate was collected and dried at50C to afford entecavir (11, 256 g, 72%) as a yellow powder, <strong>[142217-81-0]m</strong>p. 249-252C. HPLCanalysis of an aliquot of the powder indicated a purity of 99.5% (deter<strong>[142217-81-0]m</strong>ined by peakareas). 1H NMR (400 MHz, DMSO-d6): d 2.150 (1 h, <strong>[142217-81-0]m</strong>), 2.500 (1 h, <strong>[142217-81-0]m</strong>), 3.545 (2 h, <strong>[142217-81-0]m</strong>),4.233 (1 h, <strong>[142217-81-0]m</strong>), 4.564 (1 h, <strong>[142217-81-0]m</strong>), 4.837 (1 h, s), 4.875 (1 h, <strong>[142217-81-0]m</strong>), 5.100 (1 h, <strong>[142217-81-0]m</strong>), 5.338 (1 h,<strong>[142217-81-0]m</strong>), 6.426 (2 h, s), 7.664 (1 h, s), 10.611 (1 h, s). HRMS (ESI) Calcd for C12H15N5O3Na[MCNa]C: 300.1073, Found: 300.1083.
  • 12
  • C16H18O4 [ No CAS ]
  • [ 142217-81-0 ]
  • 13
  • C16H20O4 [ No CAS ]
  • [ 142217-81-0 ]
  • 14
  • C23H26O4 [ No CAS ]
  • [ 142217-81-0 ]
  • 15
  • [ 1354715-02-8 ]
  • [ 142217-81-0 ]
  • 16
  • [ 100-52-7 ]
  • [ 142217-81-0 ]
  • 17
  • C26H26ClN5O2 [ No CAS ]
  • [ 142217-81-0 ]
YieldReaction ConditionsOperation in experiment
25 mg With trifluoroacetic acid; In water; at 20℃; for 8.0h; To a solution of the product of step 1j (40 mg, 0.13 mmol) in tetrahydrofuran (3 mL) was added triphenylphosphine (68 mg, 0.26 mmol), 6-chloro-2-aminopurine(44 mg, 0.26 mmol) And diethyl azodicarboxylate (45 mg, 0.26 mmol) were added, and the mixture was stirred at room temperature for 16 hours. The organic solvent was evaporated to dryness, and the residue was redissolved in a mixed solution of trifluoroacetic acid (8 mL) and water (2 mL), and the mixture was stirred at room temperature for 8 hours. The solvent was evaporated to dryness and the residue was purified by silica gel column chromatography to give 25 mg of a white solid in 45% yield.
  • 18
  • [ 256390-84-8 ]
  • [ 142217-81-0 ]
  • 19
  • [ 139884-80-3 ]
  • [ 142217-81-0 ]
  • 20
  • [ 184376-29-2 ]
  • [ 142217-81-0 ]
  • 21
  • C12H14O2 [ No CAS ]
  • [ 142217-81-0 ]
  • 22
  • C17H24O2Si [ No CAS ]
  • [ 142217-81-0 ]
  • 23
  • C16H18O3 [ No CAS ]
  • [ 142217-81-0 ]
  • 24
  • 6-amino-4-(((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylene-cyclopentyl)amino)-3-nitropyridine-2(1H)-one [ No CAS ]
  • [ 142217-81-0 ]
  • 25
  • 3,6-diamino-4-(((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)amino)pyridin-2(1H)-one [ No CAS ]
  • [ 122-51-0 ]
  • [ 142217-81-0 ]
YieldReaction ConditionsOperation in experiment
53% With hydrogenchloride; In methanol; water; at 25 - 50℃; for 12.16h;Large scale; Hydrochloric acid (2.08 kg) was added dropwise to a mixture of compound 19 (1.04 kg,2.3 mol) and triethyl orthoformate (46 kg, 310.4 mol) at 25C over 10 min. The temperaturewas raised to 45-50C and the mixture was stirred for 12 h. After cooling to 0-5C,the precipitate was filtered and dried at 40-50C to afford 10 (595 g, 53%) as a gray powder,mp. 218-219C. HPLC analysis of an aliquot of the powder indicated a purity of 98%(determined by peak areas). 1H NMR (400 MHz, DMSO-d6): d 2.289-2.422 (2 h, m),2.984-3.015 (1 h, m), 3.617-3.635 (2 h, m), 4.101-4.111 (1 h, m), 4.515-4.594 (5 h, m),5.137-5.146 (1 h, m), 5.327-5.374 (1 h, m), 6.474 (2 h, s), 7.267-7.375 (10 h, m), 7.651(1 h, s), 10.636 (1 h, s). HRMS (ESI) Calcd for C26H27N5O3Na [MCNa]C: 480.2012,Found: 480.2024.
  • 26
  • 2-((1S,2S,3S,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-hydroxycyclopentyl)isoindoline-1,3-dione [ No CAS ]
  • [ 142217-81-0 ]
  • 27
  • 2-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-oxocyclopentyl)isoindoline-1,3-dione [ No CAS ]
  • [ 142217-81-0 ]
  • 28
  • 2-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)isoindoline-1,3-dione [ No CAS ]
  • [ 142217-81-0 ]
  • 29
  • (1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentanamine [ No CAS ]
  • [ 142217-81-0 ]
  • 30
  • [ 1351691-90-1 ]
  • [ 142217-81-0 ]
  • 31
  • C37H41N5O6 [ No CAS ]
  • [ 142217-81-0 ]
  • 32
  • C38H41N5O5 [ No CAS ]
  • [ 142217-81-0 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; In tetrahydrofuran; methanol; water; at 50℃; for 2.5h; To a 5 L three-necked flask, 64 g (0.099 mol) of the compound of the formula V and 0.9 L of tetrahydrofuran were added, stirred and dissolved, 0.9 L of CH3OH was added, 0.5 L of 2N HCl was added, the temperature was raised to 50 C, and the reaction was stirred for 2.5 h.Concentrated under reduced pressure, cooled to room temperature, extracted twice with dichloromethane.After adding 170 mL of tetrahydrofuran to dissolve, a 2N sodium hydroxide solution was adjusted to pH 7, and a solid precipitated, and then 340 mL of ethyl acetate was added and stirred overnight.Filtration, the filter cake was washed with ethyl acetate, dried and dried at 50C to give a pale yellow solid (yield: 92%).
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