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Chemical Structure| 20970-50-7 Chemical Structure| 20970-50-7

Structure of 20970-50-7

Chemical Structure| 20970-50-7

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Product Details of [ 20970-50-7 ]

CAS No. :20970-50-7
Formula : C6H8N2O
M.W : 124.14
SMILES Code : CC(C1=CN=CN1C)=O
MDL No. :MFCD08668302
InChI Key :DARZKTBWZJGBSD-UHFFFAOYSA-N
Pubchem ID :15128990

Safety of [ 20970-50-7 ]

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

Computational Chemistry of [ 20970-50-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 5
Fraction Csp3 0.33
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 33.68
TPSA ?

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

34.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.35
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

0.03
Log Po/w (WLOGP)?

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

0.62
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.

-0.66
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

0.61
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.39

Water Solubility

Log S (ESOL):?

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

-0.97
Solubility 13.2 mg/ml ; 0.106 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.

-0.32
Solubility 60.1 mg/ml ; 0.484 mol/l
Class?

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

Very 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

-1.09
Solubility 10.1 mg/ml ; 0.0815 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

Yes
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.

-7.04 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)

1.46

Application In Synthesis of [ 20970-50-7 ]

* 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 [ 20970-50-7 ]

[ 20970-50-7 ] Synthesis Path-Downstream   1~7

  • 2
  • [ 592554-79-5 ]
  • [ 75-16-1 ]
  • [ 20970-50-7 ]
YieldReaction ConditionsOperation in experiment
74% In tetrahydrofuran; diethyl ether; at 0 - 40℃; for 4h; [2515] Took crude (882) (14.2 mmol), and dissolve in THF (100 ml). Cool in an iced bath and add MeMgBr (3 Molar in diethyl ether); (22.2 ml), dropwise over 10 minutes, under N2. Let warm to 40 C. and stir for 4 hours or until reaction is complete. Cool in an iced bath and add saturated NH4Cl. Extract with ethyl acetate and then 3×with CH2Cl2. Dry with MgSO4, filter and evaporate. Store under vacuum to obtain crystals-(883)(1.78 g, 74%).
  • 3
  • [ 20970-50-7 ]
  • [ 645-54-5 ]
  • 2-benzyl-4-(1'-methyl-5'-imidazolyl)thiazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; hydrogen bromide; pyridinium hydrobromide perbromide; In methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; EXAMPLE 3 2-Benzyl-4-(1'-methyl-5'-imidazolyl)thiazole hydrochloride A solution of <strong>[20970-50-7]5-acetyl-1-methylimidazole</strong> (100 mg, 0.81 mmol) in 2.4 ml of acetic acid was stirred at 25 C. as 0.24 ml (0.30 g, 1.2 mmol) of 31% hydrobromic acid in acetic acid was added. Pyridinium bromide perbromide (0.29 g, 0.91 mmol) was added, giving an orange solution from which a yellow precipitate formed after 30 minutes. After 2.5 hours, ether (5 ml) was added. The supernatant was removed by pipet, and the precipitate was dried under a stream of nitrogen. Ethanol (6 ml) and benzylthioamide (137 mg, 0.91 mmol) were added, and the mixture was heated to reflux for 45 minutes. The reaction was cooled to 25 C., poured into 25 ml of ether, and washed with 50 ml of 1.25N aqueous sodium hydroxide. The aqueous layer was extracted with 2*25 ml of ether, and the organic extracts were combined, dried (sodium sulfate), filtered, and evaporated. The residue was purified by column chromatography on silica gel (5 g), eluted with 8% isopropanol in 4:1 dichloromethane/ethyl acetate, yielding 2-benzyl-4-(1'-methyl-5'-imidazolyl)thiazole (159 mg, 77% yield) as an almost colorless oil. The free base (159 mg, 0.62 mmol) was dissolved in 10 ml of methanol and treated with 0.32 ml (0.64 mmol) of 2.0N aqueous hydrochloric acid. Evaporation of the solution yielded 183 mg of pale yellow crystals. Recrystallization from 2:1 ethyl acetate/ethanol gave 2-benzyl-4-(1'-methyl-5'-imidazolyl)thiazole hydrochloride (111 mg, 61% recovery) as colorless plates, m.p. 191-194 C.
  • 4
  • [ 592555-19-6 ]
  • [ 20970-50-7 ]
  • C29H34ClN5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% [2516] Dissolve 365 (0.24 g, 0.49 mmol) in THF (2.5 ml). Cool under N2 to -78 C., add (1) (BuLi, 2.5M, 0.2 ml) and stir the resulting dark brown solution for 15 minutes. Dissolved 883 (0.116 g) from Step C in 0.5 mL of THF and add to reaction and stir at -78 C. for 3 hours. Add reaction mixture to brine and extract with ethyl acetate(2×). Dry with MgSO4, filter and evaporate to obtain a yellow solid. Purified crude (0.29 g) by Prep Plate Chromatography to afford 0.0.15 g, 42% yield of the desired product (795.1).
  • 5
  • [ 20970-50-7 ]
  • [ 443986-86-5 ]
  • [ 432516-76-2 ]
  • 6
  • [ 20970-50-7 ]
  • [ 426219-35-4 ]
  • [ 1346155-91-6 ]
YieldReaction ConditionsOperation in experiment
38% General procedure: nder an argon atmosphere, 9a (436 mg, 1.65 mmol) was dissolved in dry THF (30 mL) and the mixture was cooled to -65 C in a dry ice acetone bath. A n-BuLi hexane solution (1.6 M: 2.28 mL, 3.63 mmol) was added with stirring and the mixture was stirred at the same temperature for 1.5 h. After stirring, a solution of 6 (183 mg, 1.5 mmol) in dry THF (3 mL) was added dropwise and the whole was stirred at the same temperature for 1.5 h. After dilution with saturated aqueous ammonium chloride solution, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethanol and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the resulting residue was chromatographed on silica gel (CHCl3/7% ammonia in MeOH = 19:1) and crystallized from CHCl3 and diethylether to give 3c (121 mg, 26%) as a colorless powder.
 

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