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[ CAS No. 496786-98-2 ] {[proInfo.proName]}

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Chemical Structure| 496786-98-2
Chemical Structure| 496786-98-2
Structure of 496786-98-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 496786-98-2 ]

CAS No. :496786-98-2 MDL No. :MFCD04039875
Formula : C20H32BN3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :JWUBVPJWWYYRLJ-UHFFFAOYSA-N
M.W : 389.30 Pubchem ID :16217947
Synonyms :

Calculated chemistry of [ 496786-98-2 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.7
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 117.91
TPSA : 64.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.95
Log Po/w (WLOGP) : 1.68
Log Po/w (MLOGP) : 1.35
Log Po/w (SILICOS-IT) : 1.16
Consensus Log Po/w : 1.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0446 mg/ml ; 0.000115 mol/l
Class : Soluble
Log S (Ali) : -3.96
Solubility : 0.0428 mg/ml ; 0.00011 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.24
Solubility : 0.0226 mg/ml ; 0.0000581 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.85

Safety of [ 496786-98-2 ]

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

Application In Synthesis of [ 496786-98-2 ]

* 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 [ 496786-98-2 ]
  • Downstream synthetic route of [ 496786-98-2 ]

[ 496786-98-2 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
56% With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; Inert atmosphere [0951] A solution ofcompound 90b (125 g, 366 mmol) inDMF (1.30 L)was treatedwith, 4,4,4',4',5,5,5',5'-octamethyl2,2'-bi(1,3,2-dioxaborolane) (186 g, 732 mmol), Pd(OAc) 2(4.09 g, 18.3 mmol), PPh3 (19.2 g, 73.2 mmol) and KOAc(108 g, 1.10 mol) under a nitrogen atmosphere. The resultingmixture was stirred overnight at 80° C. Upon cooling to roomtemperature, the solids were collected by filtration. The filtrate was concentratedunderreduced pressure, and the resultant residue was purified by flash colunm chromatography onsilica gel (EtOAc/petroleum ether (1 :50 v/v)) to obtain compound 90c as a white solid (80.0 g, 56percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H32BN3 0 4 : 390.2(M+H). found 390.2.
2.55 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 2 h; Inert atmosphere Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (2.0 g, 5.84 mmol),Bis(boronic acid) pinacol ester (2.2 g, 8.77 mmol) andPotassium acetate (1.72 g, 17.53 mmol)To a solution of dimethyl sulfoxide (10 mL) was added Pd(dppf)Cl2.CH2Cl2 (473.0 mg, 0.58 mmol).The reaction was heated to 80°C and stirred for 2 hours.Cool toDiluted with ethyl acetate (100 mL) at room temperature and filtered through celite. The filtrate was washed with saturated brine (100 mL x 4), anhydrousSodium sulfate was dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 3/1) to give the title compoundThe product was an off-white solid (2.55 g, 112percent).
Reference: [1] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0945; 0950-0951
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5361 - 5379
[3] Patent: US2013/225548, 2013, A1, . Location in patent: Paragraph 0531; 0632
[4] Patent: CN104650049, 2018, B, . Location in patent: Paragraph 0426; 0427
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Reference: [1] Patent: WO2015/88045, 2015, A1, . Location in patent: Paragraph 0239
[2] Patent: US2017/8885, 2017, A1, . Location in patent: Paragraph 0656; 0658
[3] Patent: WO2017/38909, 2017, A1, . Location in patent: Paragraph 0308; 0309; 0311
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Reference: [1] Patent: US2014/364414, 2014, A1,
[2] Patent: CN104650049, 2018, B,
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Reference: [1] Patent: US2014/364414, 2014, A1,
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Reference: [1] Patent: CN104650049, 2018, B,
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