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Chemical Structure| 1254115-23-5 Chemical Structure| 1254115-23-5

Structure of 1254115-23-5

Chemical Structure| 1254115-23-5

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Product Details of [ 1254115-23-5 ]

CAS No. :1254115-23-5
Formula : C7H14N2O
M.W : 142.20
SMILES Code : N1(C2COC2)CCNCC1
MDL No. :MFCD21847918
InChI Key :AOYSLJHKVBSXRU-UHFFFAOYSA-N
Pubchem ID :57416287

Safety of [ 1254115-23-5 ]

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

Computational Chemistry of [ 1254115-23-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 46.15
TPSA ?

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

24.5 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.83
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

-0.7
Log Po/w (WLOGP)?

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

-1.47
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.

-0.31
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

0.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.03

Water Solubility

Log S (ESOL):?

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

-0.21
Solubility 86.7 mg/ml ; 0.61 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.

0.66
Solubility 651.0 mg/ml ; 4.58 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

-0.69
Solubility 28.9 mg/ml ; 0.203 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

Low
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

Yes
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.

-7.66 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)

1.42

Application In Synthesis of [ 1254115-23-5 ]

* 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.

  • Downstream synthetic route of [ 1254115-23-5 ]

[ 1254115-23-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 454-16-0 ]
  • [ 1254115-23-5 ]
  • 1-(2-methoxy-4-nitrophenyl)-4-(oxetan-3-yl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 100℃;Inert atmosphere; Example 9 Preparation of l-(2-Methoxy-4-nitrophenyl)-4-(oxetan-3-yl)piperazine [0231] To a round-bottomed flask equipped with a stirring bar and a nitrogen gas tee, 1- (oxetan-3-yl)piperazine (8.00 g, 56.26 mmol), l-fluoro-2-methoxy-4-nitrobenzene (9.63 g, 56.26 mmol), potassium carbonate (K2C03) (38.88 g, 281.29 mmol), and N-methyl-2- pyrrolidone (NMP) (100 mL) were added. The resulting mixture was heated at 100°C overnight. Water (500 mL) was added and the resulting mixture was extracted with ethyl acetate (200 mL X 3), the combined organic phases were washed with H20 (50 mL X 1), brine (50 mL X 1), and dried over sodium sulfate. The organic phase was filtered and removed solvent in vacuo, and passed a silica gel column (methanol: methylene chloride = 5: 95), yellow solids were obtained as the desired product.
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 16h; A mixture of <strong>[454-16-0]1-fluoro-2-methoxy-4-nitrobenzene</strong> (1.0 g, 5.8 mmol), 1-(oxetan-3-yl)piperazine (0.91 g, 6.4 mmol), and potassium carbonate (1.6 g, 12 mmol) in N,N-dimethylformamide (9 mL) was stirred at 100° C. for 16 hours. The mixture was allowed to cool to room temperature. The supernatant was removed by pipette and concentrated under reduced pressure. This residue was combined with the solids and partitioned between ethyl acetate and water. The aqueous phase was extracted three times with ethyl acetate. The combined extracts were washed twice with water, once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 1-(2-methoxy-4-nitrophenyl)-4-(oxetan-3-yl)piperazine. LCMS-ESI+ (m/z): [M+H]+ calcd for C14H2O3O4: 294.1. found: 294.2
  • 2
  • [ 105806-13-1 ]
  • [ 1254115-23-5 ]
  • N-[5-fluoro-2-methyl-6-[4-(oxetan-3-yl)piperazin-1-yl]pyrimidin-4-yl]-5-(2-pyridyl)thiazol-2-amine [ No CAS ]
  • 3
  • [ 105806-13-1 ]
  • [ 1254115-23-5 ]
  • 4-chloro-5-fluoro-2-methyl-6-[4-(oxetan-3-yl)piperazin-1-yl]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.166667h; [00343] To a mixture of <strong>[105806-13-1]4,6-dichloro-5-fluoro-2-methyl-pyrimidine</strong> (390 mg, 2.15 mmol) and diisopropylethylamine (900 mu, 5.17 mmol) in dichloromethane (3.9 mL) was added l-(oxetan-3-yl)piperazine (335 mg, 2.4 mmol) . The mixture was stirred for 10 minutes. The resulting mixture was concentrated in vacuo then purified on a 40 g silica gel cartridge eluting with 0-80% ethyl acetate/heptane to provide 4-chloro- 5-fluoro-2-methyl-6-[4-(oxetan-3-yl)piperazin-l-yl]pyrirnidine (550 mg, 89%). XH NMR (400 MHz, CDC13) delta 5.35 (s, 1H), 4.92 - 4.70 (m, 2H), 4.65 - 4.41 (m, 2H), 4.68 - 4.12 (m, 2H), 2.46 (d, J = 1.1 Hz, 3H), 1.79 (d, J = 0.7 Hz, 3H) ppm. ESI-MS m/z calc. 231.05746, found 232.0 (M+l) +; Retention time: 0.65 minutes.
 

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