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[ CAS No. 88095-61-8 ] {[proInfo.proName]}

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Chemical Structure| 88095-61-8
Chemical Structure| 88095-61-8
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Product Details of [ 88095-61-8 ]

CAS No. :88095-61-8 MDL No. :MFCD03087886
Formula : C10H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IYZHZCMFLIKMSN-UHFFFAOYSA-N
M.W : 203.20 Pubchem ID :973645
Synonyms :

Calculated chemistry of [ 88095-61-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.1
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.8
TPSA : 63.64 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 1.66
Log Po/w (WLOGP) : 1.84
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : -0.38
Consensus Log Po/w : 1.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.657 mg/ml ; 0.00323 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.499 mg/ml ; 0.00245 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.389 mg/ml ; 0.00191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 88095-61-8 ]

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 [ 88095-61-8 ]

* 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 [ 88095-61-8 ]
  • Downstream synthetic route of [ 88095-61-8 ]

[ 88095-61-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 88095-61-8 ]
  • [ 28466-62-8 ]
Reference: [1] Patent: US2010/120874, 2010, A1, . Location in patent: Page/Page column 28
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5714 - 5727
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3806 - 3816
[4] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2382 - 2390
  • 2
  • [ 50877-42-4 ]
  • [ 88095-61-8 ]
YieldReaction ConditionsOperation in experiment
63% With nitric acid In tetrahydrofuran; water at 20℃; for 3.5 h; General procedure: To iodopyrazole (1 mmol) dissolved in THF (10 mL), Fuajasite (250 mg) was added. Nitric acid (d 1.52 g/cm3, 10 mL) was added slowly and the mixture was stirred at room temperature for required time. The catalyst was recovered by filtration and the filtrate was extracted repeatedly with dichloromethane. The solvent was removed under vacuum to obtain nitropyrazole.
Reference: [1] Synthetic Communications, 2012, vol. 42, # 23, p. 3463 - 3471
[2] Catalysis Communications, 2013, vol. 42, p. 35 - 39
  • 3
  • [ 2075-46-9 ]
  • [ 100-39-0 ]
  • [ 88095-61-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere
Stage #2: at 0 - 20℃; for 12 h; Inert atmosphere
a)
1-Benzyl-4-nitro-1H-pyrazole
To a solution of 4-nitro-1H-pyrazole (283 mg, 2.5 mmol) in dry DMF (5 ml) under an argon atmosphere was added NaH (120 mg, 2.75 mmol) in small portions at 0° C.
The reaction mixture was stirred at rt for 1 hour, cooled again to 0° C. before benzyl bromide (300 μl, 2.5 mmol) was added and stirred at rt for 12 h.
The mixture was diluted with water, extracted with ethyl acetate and the product was purified by chromatography on silica gel using heptane/ethyl acetate as eluent.
The title compound was obtained as light yellow oil (484 mg, 95percent). MS ISP (m/e): 226.3 (100) [(M+Na)+].
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5714 - 5727
[2] Patent: US2010/120874, 2010, A1, . Location in patent: Page/Page column 27-28
  • 4
  • [ 2075-46-9 ]
  • [ 620-05-3 ]
  • [ 88095-61-8 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16 h; General procedure: To a stirred solution of 4-nitroimidazole or 4-nitropyrazole (1.00 g, 8.84 mmol) in DMF (6.00 mL) at 25°C were added K2CO3 (1.47 g, 10.6 mmol) and alkyl iodide(10.6 mmol). After stirring for 16 h at 25 °C, the reactionmixture was treated with water (15 mL) and EtOAc (20 mL)and transferred to a 125 mL separatory funnel. The organiclayer was collected and the aqueous layer was extracted withEtOAc (25 mL × 2). The combined organic layers werewashed with brine (20 mL), dried over sodium sulfate andfiltered. The filtrate was concentrated, and the residue waspurified by flash column chromatography to provide thecorresponding alkyl azole.
Reference: [1] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 10, p. 3009 - 3014
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2382 - 2390
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