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Chemical Structure| 17768-41-1 Chemical Structure| 17768-41-1

Structure of Adamantan-1-ylmethanamine
CAS No.: 17768-41-1

Chemical Structure| 17768-41-1

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Product Details of [ 17768-41-1 ]

CAS No. :17768-41-1
Formula : C11H19N
M.W : 165.28
SMILES Code : NCC12CC3CC(C2)CC(C3)C1
MDL No. :MFCD00074750
InChI Key :XSOHXMFFSKTSIT-UHFFFAOYSA-N
Pubchem ID :86625

Safety of [ 17768-41-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:2735
Packing Group:

Computational Chemistry of [ 17768-41-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 51.1
TPSA ?

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

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.31
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

2.19
Log Po/w (WLOGP)?

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

2.16
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.

2.74
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

2.21
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.32

Water Solubility

Log S (ESOL):?

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

-2.18
Solubility 1.1 mg/ml ; 0.00663 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.

-2.37
Solubility 0.705 mg/ml ; 0.00426 mol/l
Class?

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

-1.98
Solubility 1.72 mg/ml ; 0.0104 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.

-5.75 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

2.0
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)

3.59

Application In Synthesis of [ 17768-41-1 ]

* 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 [ 17768-41-1 ]

[ 17768-41-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 17768-41-1 ]
  • [ 10165-86-3 ]
  • methyl 6-((((adamantan-1-yl)methyl)amino)methyl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 3h; A mixture of methyl 6-formylnicotinate (0.320 g, 1.938 mmol) and (adamantan-1-yl)methanamine (0.416 mL, 2.5 19 mmol) in dichloromethane (20 mL) was treated at the room temperature with sodium triacetoxyborohydride (0.821 g, 3.875 mmol), and stirred at the same temperature for 3 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The residue was chromatographed (5i02, 12 g cartridge; ethyl acetate / hexane = 30 percent to 70 percent) to give methyl 6-((((adamantan-1-yl)methyl)amino)methyl)nicotinate as yellow oil (0.530 g, 87.0 percent).
39% A solution of methyl 4-formylnicotinic acid (100 mg, 0.606 mol 1.0 eq.) and 1- adamantanemethylamine (100 mg, 0.606 mol, 1.0 eq.) in 2 mL methanol was stirred for 2 h at room temperature. Next, 150 mg sodium triacetoxyborohydride was added and the reaction mixture was stirred until no starting material remained. The mixture was concentrated in vacuo, partitioned between ethyl acetate and water, the aqueous layer extracted two more times with ethyl acetate and the combined organic phases were dried over sodium sulfate. The solvent was removed under reduced pressure and the product was purified by column chromatography. The title product (75 mg, 0.239 mmol, 39percent) was obtained as a clear oil. 1H NMR (500 MHz, Chloroform-d) delta 9.15 (d, J = 2.2 Hz, 1H), 8.26 (dd, J = 8.2, 2.1 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H), 3.97 (s, 2H), 3.96 (d, j = 1.6 Hz, 3H), 2.27 (s, 2H), 1.98 (s, 3H), 1.80 - 1.61 (m, 6H), 1.55 (d, j = 2.8 Hz, 6H).
  • 2
  • [ 17768-41-1 ]
  • [ 3356-89-6 ]
  • N-(1-adamantylmethyl)-3-phenylisoxazol-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With potassium carbonate; In N,N-dimethyl-formamide; for 1.5h;Reflux; General procedure: A mixture of <strong>[3356-89-6]5-chloro-3-phenylisoxazole</strong> (2) (5 mmol), amine (10 mmol) and K2CO3 (15 mmol) in DMF (25 mL) was refluxed under stirring for 1.5 h. The reaction mixture was cooled and diluted with cold H2O (40 mL). For 5a and 5b, the resulting precipitate was collected, washed with H2O and recrystallized from hexane-Et2O. For 5c-e, the reaction mixture was extracted with CH2Cl2 (3 × 20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane-EtOAc, 5:1). 5-Aminoisoxazoles 5a and 5b are known compounds and have full characterization data.
  • 3
  • [ 17768-41-1 ]
  • [ 10165-86-3 ]
  • 6-((((adamantan-1-yl)methyl)amino)methyl)-N-hydroxynicotinamide [ No CAS ]
  • 4
  • [ 17768-41-1 ]
  • [ 175205-81-9 ]
  • N-(adamantan-1-ylmethyl)-4-(trifluoromethyl)-pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With copper(l) iodide; 2-(2-methyl-1-oxopropyl)cyclohexanone; caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h;Schlenk technique; General procedure: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data
  • 5
  • [ 17768-41-1 ]
  • [ 175205-81-9 ]
  • N-(adamantan-1-ylmethyl)-4-(trifluoromethyl)-pyridin-2-amine [ No CAS ]
  • N-(adamantan-1-ylmethyl)-4-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
40%; 47% With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 12h;Schlenk technique; General procedure: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data
45%; 12% With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 12h;Schlenk technique; General procedure: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data
  • 6
  • [ 20291-40-1 ]
  • [ 17768-41-1 ]
  • methyl 7-((((3r,5r,7r)-adamantan-1-yl)methyl)amino)-7-oxoheptanoate [ No CAS ]
 

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