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[ CAS No. 839714-33-9 ] {[proInfo.proName]}

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Chemical Structure| 839714-33-9
Chemical Structure| 839714-33-9
Structure of 839714-33-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 839714-33-9 ]

CAS No. :839714-33-9 MDL No. :MFCD11098002
Formula : C6H11BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RWQOGZHKBNANKP-UHFFFAOYSA-N
M.W : 153.98 Pubchem ID :23139440
Synonyms :

Calculated chemistry of [ 839714-33-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.93
TPSA : 58.28 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.13
Log Po/w (WLOGP) : -0.86
Log Po/w (MLOGP) : -1.01
Log Po/w (SILICOS-IT) : -1.77
Consensus Log Po/w : -0.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.92
Solubility : 18.6 mg/ml ; 0.121 mol/l
Class : Very soluble
Log S (Ali) : -0.64
Solubility : 35.3 mg/ml ; 0.229 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.11
Solubility : 120.0 mg/ml ; 0.78 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 839714-33-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 839714-33-9 ]

* 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 [ 839714-33-9 ]
  • Downstream synthetic route of [ 839714-33-9 ]

[ 839714-33-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 18952-87-9 ]
  • [ 839714-33-9 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2.5 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran at 20℃; for 0.75 h;
Stage #3: With hydrogenchloride In tetrahydrofuran
2-Isopropyl-2H-pyrazole-3-boronic acid:
n-BuLi (17.46 g, 110 ml, 273 mM, in hexanes) was slowly added over 30 minutes at -78°C to a THF solution of 1-isopropyl-1H-pyrazole (25.0 g, 227 mmol).
The reaction mixture was stirred at -78°C for 2 hours.
A solution of cooled triisopropoxy boronate (170.0 g, 909 mmol) was added slowly via canula over 45 minutes.
The reaction mixture was allowed to warm to room temperature and stirred overnight.
The reaction mixture was adjusted to pH 6-7 with HCl (1M, 170 mL).
The solvent was evaporated to dryness and the resulting residue was triturated with 1:1 ethylacetate:dichloromethane, the suspension filtered and the solvent was evaporated in vacuo to yield 2-isopropyl-2H-pyrazole-3-boronic acid as a colorless solid (20.0 g, 58percent).
LCMS m/z (percent) = 154 M+H+, (100).
1H NMR (400 MHz, DMSO-d6) δ: 8.14 (s, 2H), 7.2 (s, 1H), 6.5 (s, 1H), 5.05 (m, 1H), 1.2 (d, J= 9.0 Hz, 6H).
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1923 - 1936
[2] Patent: WO2005/12254, 2005, A1, . Location in patent: Page/Page column 129
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  • [ 688-74-4 ]
  • [ 18952-87-9 ]
  • [ 839714-33-9 ]
Reference: [1] Patent: US2009/170873, 2009, A1, . Location in patent: Page/Page column 48
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