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Chemical Structure| 130290-79-8 Chemical Structure| 130290-79-8

Structure of 130290-79-8

Chemical Structure| 130290-79-8

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Product Details of [ 130290-79-8 ]

CAS No. :130290-79-8
Formula : C6H13NO
M.W : 115.17
SMILES Code : NCC1CCOCC1
MDL No. :MFCD02179435
InChI Key :IPBPLHNLRKRLPJ-UHFFFAOYSA-N
Pubchem ID :2773210

Safety of [ 130290-79-8 ]

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 [ 130290-79-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 32.63
TPSA ?

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

35.25 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.65
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

-0.12
Log Po/w (WLOGP)?

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

0.37
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.

0.21
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

1.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.63

Water Solubility

Log S (ESOL):?

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

-0.41
Solubility 44.6 mg/ml ; 0.387 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.

-0.17
Solubility 78.4 mg/ml ; 0.681 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

-0.77
Solubility 19.6 mg/ml ; 0.171 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.

-7.09 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 [ 130290-79-8 ]

* 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 [ 130290-79-8 ]

[ 130290-79-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 130290-79-8 ]
  • [ 862695-75-8 ]
  • [ 862695-76-9 ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20.0℃; Description 14: 6-Chloro-2-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide; To a solution of <strong>[862695-75-8]6-chloro-2-cyclopropyl-nicotinic acid</strong> (Description 13) (2. 1g) in dimethylformamide (20ml) was added 1-hydroxybenzotriazole (730mg), 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (2. 31 g), N-ethyl morpholine (3. 2ml) followed by (tetrahydro-pyran-4-yl) -methylamine (1.9g). The mixture was stirred at room temperature overnight. Water (100ml) was added and the mixture was extracted with ethyl acetate (2x 100ml). The combined organic layers were washed with 10% sodium hydrogen carbonate (100ml), and brine (50ml). The dried (Na2SO4) organic layer was evaporated under reduced pressure. The residue was purified by Biotage chromatography over silica using ethyl acetate (60%) /isohexane (40%) to give the title compound (2. 81g) as a white solid. NMR (MeOD) b 0.96-1. 10 (4H, m), 1.28-1. 41 (2H, m), 1.65-1. 73 (2H, m), 1.80-1. 94 (1H, m), 2.24-2. 33 (1H, m), 3.24-3. 29 (2H, m), 3.37-3. 47 (2H, m), 3. 92-4.00 (2H, m), 7.16 (1H, d), 7.6 2 (1H, d). LC/MS t= 2. 39 min, molecular ion observed [MH] = 295 consistent with molecular formula C15H19ClN2O2
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20.0℃; Intermediate 29: 6-Chloro-2-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide; To a solution of <strong>[862695-75-8]6-chloro-2-cyclopropyl-nicotinic acid</strong> (2. 1g) in dimethylformamide (20ml) was added 1-hydroxybenzotriazole (730mg), 1- [3- (dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (2. 3 1 g), N-ethyl morpholine (3. 2ml) followed by (tetrahydro-pyran-4-yl)- methylamine (1.9g). The mixture was stirred at room temperature overnight. Water (100ml) was added and the mixture was extracted with ethyl acetate (2x 100ml). The combined organic layers were washed with 10% sodium hydrogen carbonate (100ml), and brine (50ml). The dried (Na2S04) organic layer was evaporated under reduced pressure. The residue was purified by Biotage chromatography over silica using ethyl acetate (60%) /isohexane (40%) to give the title compound (2. 81g) as a white solid. NMR (MeOD) 8 0.96-1. 10 (4H, m), 1. 28-1. 41 (2H, m), 1.65-1. 73 (2H, m), 1.80-1. 94 (1H, m), 2. 24-2. 33 ( H, m) ; 3.24-3. 29 (2H, m), 3 37 - 3. 47 (2H, m), 3.92-4. 00 (2H, m), 7.16 (1H, d), 7. 6 2 (1H, d). LC/MS t= 2. 39 min, molecular ion observed [MH] = 295 consistent with molecular formula C15Hl9CIN202
  • 2
  • [ 130290-79-8 ]
  • [ 723280-98-6 ]
  • [ 723283-83-8 ]
YieldReaction ConditionsOperation in experiment
Triethylamine (43 mL, 0.31 mol) was added in a single portion to a chilled (ice bath) suspension of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (60 g, (0.21 mol) in DMF (200 mL) to provide a solution. A solution of 1 -tetrahydro-2H-pytauan-4-ylmethylamine (36 g, 0.31 mole) in DMF (50 mL) was added dropwise. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was chilled in an ice bath, then quenched with water (150 mL), and then stirred for 30 minutes. A solid was isolated by filtration, washed sequentially with water and diethyl ether, and then dried at 65 0C in a vacuum oven to provide 36.2 g of (7-bromo-3-nitroquinolin-4-yl)(tetrahydro-2H-pyran-4- ylmethyl)amine as a yellow solid.
  • 3
  • [ 130290-79-8 ]
  • [ 325142-82-3 ]
  • N-((tetrahydro-2H-pyran-4-yl)methyl)-3-(trifluoromethyl)aniline [ No CAS ]
  • 4
  • [ 130290-79-8 ]
  • [ 579514-75-3 ]
  • C17H24N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethanol; General procedure: To a solution fo <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (560 mg, 2.3 mmol) in 20mL of EtOH were added butan-1-amine (853 mg, 11.6 mmol) and stirred at rt for 2 h.The reaction mixture was concentrated to dryness, and the residue was dissolved inEtOAc (10 x 3 mL) and washed with brine (10 mL). The combined organic layerswere dried over MgSO4, and concentrated in vacuo to afford the product tert-butyl 4-(butylamino)-3-nitrobenzoate (35b) as yellow-orange solid (490 g, 72% yield).
  • 5
  • [ 130290-79-8 ]
  • 1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde [ No CAS ]
  • [ 349-02-0 ]
  • 2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazole-5-carboxamide [ No CAS ]
 

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Technical Information

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