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Chemical Structure| 84547-61-5 Chemical Structure| 84547-61-5

Structure of 84547-61-5

Chemical Structure| 84547-61-5

(1-Methyl-1H-pyrazol-5-yl)methanol

CAS No.: 84547-61-5

4.5 *For Research Use Only !

Cat. No.: A237158 Purity: 98%

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Product Details of [ 84547-61-5 ]

CAS No. :84547-61-5
Formula : C5H8N2O
M.W : 112.13
SMILES Code : OCC1=CC=NN1C
MDL No. :MFCD08556301
InChI Key :WQFOGLYQVFBDEY-UHFFFAOYSA-N
Pubchem ID :11815316

Safety of [ 84547-61-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 84547-61-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 5
Fraction Csp3 0.4
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 29.62
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

38.05 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.94
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.62
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.24
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.53
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.19
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.05

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.54
Solubility 32.3 mg/ml ; 0.288 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

0.29
Solubility 220.0 mg/ml ; 1.96 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.57
Solubility 30.4 mg/ml ; 0.271 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.42 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.32

Application In Synthesis of [ 84547-61-5 ]

* 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 [ 84547-61-5 ]
  • Downstream synthetic route of [ 84547-61-5 ]

[ 84547-61-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 16034-46-1 ]
  • [ 84547-61-5 ]
YieldReaction ConditionsOperation in experiment
67% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere To a solution of 1 -methyl- lH-pyrazole-5-carboxylic acid (2 g, 15.86 mmol) in tetrahydrofuran (50 mL) was added L1AIH4 (720 mg, 18.97 mmol) in portions at 0 °C under an inert atmosphere of nitrogen. The reaction was stirred for 2 hours at room temperature then quenched by the addition of water (2 mL). The mixture was dried over by anhydrous sodium sulfate and the solids were filtered out. The filtrates were concentrated under reduced pressure to afford (1 -methyl- lH-pyrazol- 5-yl)methanol as colorless oil (1.2 g, 67 ). (ES, m/z) [M+H]+ 113.0 *H NMR (300 MHz, CDC13) δ 7.36 (d, 7 = 1.8 Hz, 1H), 6.18 (d, 7 = 1.8 Hz, 1H), 4.66 (s, 2H), 3.88 (s, 3H)
References: [1] Patent: WO2014/66795, 2014, A1, . Location in patent: Paragraph 0175.
[2] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 11, p. 2297 - 2303[3] Zhurnal Obshchei Khimii, 1982, vol. 52, # 11, p. 2598 - 2605.
[4] Patent: WO2014/151142, 2014, A1, .
[5] Patent: WO2016/29454, 2016, A1, . Location in patent: Page/Page column 64.
  • 2
  • [ 17827-60-0 ]
  • [ 84547-61-5 ]
YieldReaction ConditionsOperation in experiment
83.3% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12 h; To a stirred solution of methyl l-methyl-lH-pyrazole-5-carboxylate (3 g, 21.4 mmol) in tetrahydrofuran (50 mL) at 0 °C was added lithium aluminum hydride (977 mg, 25.7 mmol). The mixture was stirred at room temperature for 12 h. The reaction was quenched by adding water, extracted with ethyl acetate (100 mL), dried, concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ acetic ester =10: 1), to afford the title compound as an off-white oil (2 g, 83.3percent).
References: [1] Patent: WO2014/151142, 2014, A1, . Location in patent: Paragraph 0093.
  • 3
  • [ 27258-33-9 ]
  • [ 84547-61-5 ]
References: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386.
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 11, p. 1409 - 1414.
[3] Patent: EP1422228, 2004, A1, . Location in patent: Page 221-222.
[4] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 10, p. 1099 - 1104.
[5] Patent: WO2008/125600, 2008, A2, . Location in patent: Page/Page column 30.
  • 4
  • [ 930-36-9 ]
  • [ 68-12-2 ]
  • [ 84547-61-5 ]
  • [ 84547-62-6 ]
References: [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 4, p. 961 - 982.
  • 5
  • [ 84547-59-1 ]
  • [ 84547-61-5 ]
References: [1] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 11, p. 2297 - 2303[2] Zhurnal Obshchei Khimii, 1982, vol. 52, # 11, p. 2598 - 2605.
 

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