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Structure of 50541-93-0

Chemical Structure| 50541-93-0

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Product Details of [ 50541-93-0 ]

CAS No. :50541-93-0
Formula : C12H18N2
M.W : 190.28
SMILES Code : C2=C(CN1CCC(N)CC1)C=CC=C2
MDL No. :MFCD00006504
InChI Key :YUBDLZGUSSWQSS-UHFFFAOYSA-N
Pubchem ID :415852

Safety of [ 50541-93-0 ]

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

Computational Chemistry of [ 50541-93-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 62.85
TPSA ?

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

29.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.26
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

1.37
Log Po/w (WLOGP)?

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

1.08
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.

1.74
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

1.76
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.64

Water Solubility

Log S (ESOL):?

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

-2.07
Solubility 1.63 mg/ml ; 0.00855 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-1.59
Solubility 4.92 mg/ml ; 0.0259 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

-2.94
Solubility 0.219 mg/ml ; 0.00115 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.

-6.49 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)

1.6

Application In Synthesis of [ 50541-93-0 ]

* 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 [ 50541-93-0 ]

[ 50541-93-0 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 50541-93-0 ]
  • [ 72411-89-3 ]
  • [ 72412-47-6 ]
  • 2
  • [ 50541-93-0 ]
  • [ 1798-06-7 ]
  • <i>N</i>-(1-benzyl-piperidin-4-yl)-2-(4-iodo-phenyl)-acetamide [ No CAS ]
  • 3
  • [ 50541-93-0 ]
  • [ 31872-62-5 ]
  • [ 842143-52-6 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In ethanol; for 54h;Heating / reflux; A mixture of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (4.34 g, 28.1 MMOL), 4-AMINO-1- benzypiperidine (6.01 g, 30.9 MMOL), and NaOAc (2.31 g, 28.1 MMOL) in absolute ethanol (20 mL) was stirred at reflux for 54 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in CH2CI2 (100 mL) and washed with water (2 x 30 mL). The organic layer was dried over anhydrous MgS04 and concentrated in vacuo to provide the product (8. 78 g) as a dark yellow solid. 1 H NMR (400 MHz, CDCI3) 5 9.21 (s, 1 H), 8.26 (dd, J = 6.0, 0. 4 Hz, 1 H), 8.20 (broad d, J = 7.1 Hz, 1 H), 7.34-7. 25 (complex m, 5 H), 6.70 (d, J = 6.0 Hz, 1 H), 3.62-3. 53 (m, 1 H), 3.55 (s, 2 H), 2. 89-2. 79 (m, 2 H), 2.30-2. 20 (m, 2 H), 2.10-2. 00 (m, 2 H), 1.76-1. 65 (m, 2 H).
  • 4
  • [ 51171-02-9 ]
  • [ 50541-93-0 ]
  • [ 784155-40-4 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol;Heating / reflux; A mixture of methyl 2-bromopyrazine-3-carboxylate (J. Med. Chem. , 1969, 12, 285) (2.2 g, 10.1 mmol) and 4-AMINO-1-BENZYLPIPERIDINE (2.0 g, 10.5 mmol) was refluxed in 2- propanol overnight. Thin layer chromatography (10% methanol in ethyl acetate) showed the reaction was complete. The solvent was evaporated, and the crude product dissolved in chloroform (100 mL), which was washed with saturated sodium carbonate solution (20 ML), and dried over magnesium sulfate. The title compound was obtained as a gum (3.8 g). MS 327 (M+1).
  • 5
  • [ 50541-93-0 ]
  • [ 38871-41-9 ]
  • [ 66411-12-9 ]
YieldReaction ConditionsOperation in experiment
77% With hydrogenchloride; ammonia; In chloroform; water; EXAMPLE 42 N-(1-benzyl-4-piperidyl)-1,4-benzodioxane-5-carboxamide hydrochloride 200 ml of chloroform and 50 g of 1-benzyl-4-amino piperidine were introduced into a balloon flask provided with an agitator and a thermometer, and then 50 g of <strong>[38871-41-9]1,4-benzodioxane-5-carbonyl chloride</strong> was added in portions at a temperature of from 5-10 C. After agitation of the mixture at ambient temperature the solvent was removed under vacuum and the residue was dissolved in 300 ml of water. After precipitation of the base by addition of ammonia, the water was removed and the resulting product was treated with a solution of hydrochloric acid. 75 g of N-(1-benzyl-4-piperidyl)-1,4-benzodioxane-5-carboxamide hydrochloride was produced (M.P.: 205 C.; yield: 77%).
  • 6
  • [ 207399-07-3 ]
  • [ 50541-93-0 ]
  • C48H61N4(1+)*I(1-) [ No CAS ]
  • 7
  • [ 50541-93-0 ]
  • [ 51997-51-4 ]
  • 3-[(1-Benzylpiperidin-4-yl)amino]-1-(9H-carbazol-4-yloxy)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% To a solution of 4-(2,3-Epoxypropoxy)-carbazole (1 g, 4.1 mmol) in THF (30 mL) cooled to 5-10 0C, was added LiClO4 (0.44 g, 4.1 mmol) and the reaction mixture was stirred for 15 minutes. 4-Amino-l-benzylpipe?dine (1.26 mL, 6.2 mmol) was added dropwise to the above reaction mixture at room temperature and stirring was continued for 12 hours. To the reaction mixture 50 mL of saturated NH4Cl was added EPO <DP n="44"/>and stirring was continued for 5 minutes, subsequently the solution was extracted with dichloromethane (100 rnL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the crude compound as light brown colored paste. The crude compound was purified by silica gel column chromatography, using DCM/MeOH (7:3) to afford the title compound as pale yellow colored solid (1.2 g, 65 % yield).
65% Step 1: Preparation of 3-[(1-benzylpiperidin-4-yl)amino]-1-(9H-carbazol-4-yloxy)pro-pan-2-ol To a solution of 4-(2,3-Epoxypropoxy)-carbazole (1 g, 4.1 mmol) in THF (30 mL) cooled to 5-10 C., was added LiClO4 (0.44 g, 4.1 mmol) and the reaction mixture was stirred for 15 minutes. 4-amino-1-benzylpiperidine (1.26 mL, 6.2 mmol) was added dropwise to the above reaction mixture at room temperature and stirring was continued for 12 hours. To the reaction mixture 50 mL of saturated NH4Cl was added and stirring was continued for 5 minutes, subsequently the solution was extracted with dichloromethane (100 mL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the crude compound as light brown colored paste. The crude compound was purified by silica gel column chromatography, using DCM/MeOH (7:3) to afford the title compound as pale yellow colored solid (1.2 g, 65% yield).
  • 8
  • [ 50541-93-0 ]
  • [ 151229-84-4 ]
  • [ 1335032-54-6 ]
  • [ 1335032-57-9 ]
YieldReaction ConditionsOperation in experiment
75%; 21% With triethylamine; In tetrahydrofuran; ethanol; for 12.0h;Reflux; General procedure: The <strong>[151229-84-4]2,6-dichloropyridine-3,5-dicarbonitrile</strong>s 14 [27]-15 [28] were suspended in a mixture of THF/EtOH (2:1, v:v). Then, amine 22 or 24 [41] followed by triethylamine, were added. The mixture was then heated under reflux. After cooling, the solvent was removed in vacuo and the resulting crude submitted to flash column chromatography.
75%; 21% With triethylamine; In tetrahydrofuran; ethanol; at 20℃; General procedure: 2,6-Dichloro-4-phenylpyridine-3,5-dicarbonitrile 13 or <strong>[151229-84-4]2,6-dichloropyridine-3,5-dicarbonitrile</strong> 14 was suspended in a mixture of THF/EtOH (2:1, v:v). The corresponding amines 9-12, followed by triethylamine, were then added. The mixture was then heated under reflux. After cooling, the solvent was removed in vacuum and the resulting crude submitted to flash column chromatography, to give compounds 1-8.
  • 9
  • [ 18740-39-1 ]
  • [ 50541-93-0 ]
  • C18H19ClN4S [ No CAS ]
  • 10
  • [ 50541-93-0 ]
  • [ 6322-83-4 ]
  • [ 924416-43-3 ]
YieldReaction ConditionsOperation in experiment
Preparation Example 73 Synthesis of Compound 73 (0336) (0337) Hydroxybenzophenone 2, methyl chloroacetate and K2CO3 were mixed in acetone, refluxed and stirred to afford ester 3 (step a). After completion of the reaction, an aqueous NaOH solution was added thereto, followed by acidification with HCl to obtain carboxylic acid 4 (step b). Then, 4-amino-1-benzylpiperidine was added to the carboxylic acid 4, followed by conducting the reaction in the same manner as in the preparation example 12, using carbonyl diimidazole (CDI) as a condensing agent, to obtain Compound 73. (0338) 1H-NMR (600 MHz, DMSO-d6): delta 8.04 p.p.m. (d, j=8.0 Hz, 1H), 7.74 (d, J=9.1 Hz, 2H), 7.68 (d, J=7.1 Hz, 2H), 7.65 (t, j=7.6 Hz, 1H), 7.55 (t, j=5.8 Hz, 2H), 7.27-7.32 (m, 4H), 7.23 (t, J=7.1 Hz, 1H), 7.09 (d, J=9.0 Hz, 2H), 4.58 (s, 2H), 3.63 (m, 1H), 3.44 (s, 2H), 2.74 (d, J=11.7 Hz, 2H), 1.99 (t, J=11.5 Hz, 2H), 1.70 (d, J=9.8 Hz, 2H), 1.50 p.p.m. (dq, J1=3.0 Hz, J2=11.9 Hz, 2H); (0339) 13C-NMR (150 MHz, DMSO-d6): delta 194.4, 166.2, 161.5, 138.6, 137.7, 132.2, 132.0, 129.8, 129.3, 128.7, 128.5, 128.1, 126.8, 114.6, 66.9, 62.1, 51.9, 46.1, 31.4
  • 11
  • [ 50541-93-0 ]
  • [ 935693-62-2 ]
  • 12
  • [ 50541-93-0 ]
  • [ 42926-52-3 ]
  • C21H26N2O2 [ No CAS ]
  • 13
  • [ 50541-93-0 ]
  • [ 546-43-0 ]
  • C27H38N2O2 [ No CAS ]
  • 14
  • [ 50541-93-0 ]
  • [ 16499-62-0 ]
  • N-(1-benzylpiperidin-4-yl)-7-fluoroquinazolin-4-amine [ No CAS ]
  • 15
  • [ 98556-31-1 ]
  • [ 50541-93-0 ]
  • N-(1-benzylpiperidin-4-yl)-6-iodoquinazolin-4-amine [ No CAS ]
 

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