172478-01-2|tert-Butyl methyl(piperidin-3-yl)carbamate| Ambeed

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Quality Control of [ 172478-01-2 ] Purity: 97% SDS Specification

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Product Details of [ 172478-01-2 ]

CAS No. :	172478-01-2
Formula :	C₁₁H₂₂N₂O₂
M.W :	214.30
SMILES Code :	O=C(OC(C)(C)C)N(C)C1CNCCC1
MDL No. :	MFCD06656642
InChI Key :	RTXNDTNDOHQMTI-UHFFFAOYSA-N
Pubchem ID :	22449166

Safety of [ 172478-01-2 ]

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

Computational Chemistry of [ 172478-01-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	0
Fraction Csp3	0.91
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	64.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.57 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.81
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.24
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.22
Log P_o/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.	1.15
Log P_o/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	0.76
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.44

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.69
Solubility	4.42 mg/ml ; 0.0206 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.	-1.71
Solubility	4.17 mg/ml ; 0.0195 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	-1.72
Solubility	4.08 mg/ml ; 0.0191 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.	-6.73 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	0.0
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)	2.79

Application In Synthesis of [ 172478-01-2 ]

* 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 [ 172478-01-2 ]

[ 172478-01-2 ] Synthesis Path-Downstream 1~26

1
[ 123-62-6 ]
[ 172478-01-2 ]
[ 172478-03-4 ]

References: [1]Tetrahedron,1995,vol. 51,p. 11547 - 11556.

2
[ 172477-99-5 ]
[ 172478-01-2 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; hydrogen; In methanol; at 20℃; under 760.051 Torr;	To a solution of tert-butyl ((1-benzyl-4-hydroxypiperidin-4-yl)methyl)carbamate (1.3 g, 4.3 mmol) in methanol (20 mL) was added Pd/C (130 mg). The mixture was stirred at room temperature under H2 atmosphere (1 atm) overnight then filtered. The filtrate was concentrated under vacuum to give to give crude tert-butyl methyl(piperidin-3-yl)carbamate as a residue.

References: [1]Tetrahedron,1995,vol. 51,p. 11547 - 11556.
[2]Patent: WO2017/216726,2017,A1 .Location in patent: Page/Page column 566.

3
[ 40114-49-6 ]
[ 172478-01-2 ]

References: [1]Tetrahedron,1995,vol. 51,p. 11547 - 11556.
[2]Patent: WO2017/216726,2017,A1 .

4
[ 60717-45-5 ]
[ 172478-01-2 ]

References: [1]Tetrahedron,1995,vol. 51,p. 11547 - 11556.
[2]Patent: WO2017/216726,2017,A1 .

5
[ 172478-01-2 ]
[ 172478-05-6 ]

References: [1]Tetrahedron,1995,vol. 51,p. 11547 - 11556.

6
[ 172478-01-2 ]
3-<methyl-(1-phenylpropen-3-yl)amino>-1-propionyl-piperidine [ No CAS ]

References: [1]Tetrahedron,1995,vol. 51,p. 11547 - 11556.

7
[ 1279817-03-6 ]
[ 172478-01-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;5% rhodium-on-charcoal; In ethanol; at 25℃; under 3102.97 Torr; for 27h;Paar apparatus;	A mixture of tert-butyl 3-pyridinylmethylcarbamate (4.3 g) and 5% rhodium on carbon (400 mg) in ethanol (50 mL) at 25 C. in a paar apparatus was stirred under hydrogen at 60 pounds per square inch for 27 hours, filtered through diatomaceous earth (Celite), and concentrated. 1H NMR (300 MHz, CDCl3) delta 4.55 (b, 1H), 2.99 (m, 4H), 2.56 (t, 1H), 2.33 (t, 1H), 1.74 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H).

References: [1]Patent: US2005/159423,2005,A1 .Location in patent: Page/Page column 18.
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5580 - 5590.

8
[ 406213-47-6 ]
[ 74-88-4 ]
[ 172478-01-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 26; N-methyl-N-(piperidin-3-yl) carbamic acid t-butyl ester; [] In a water bath at room temperature, sodium hydride (60% in oil) (0.4 g) was added to a mixture of 3-t-butoxycarbonylaminopiperidin-1-carboxylic acid benzyl ester (compound 25a) (3.3 g), methyl iodide (0.75 mL), and N,N-dimethylformamide (20 mL), and this was stirred at room temperature for four hours. The reaction solution was extracted using ethyl acetate and water, the organic layer was washed with water, and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography using 10% to 20% ethyl acetate/ hexane to give an oily substance (3.04 g). A mixture of all of the resulting material with ethanol (20 mL) and 10% palladium on carbon was stirred under hydrogen atmosphere at room temperature for five hours. The catalyst was filtered off, and the filtrate was concentrated to give the title compound (1.82 g).
	palladium-carbon; In ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide;	(a) t-Butyl N-methyl-N-(piperidin-3-yl)carbamate 0.4 g of sodium hydride (60%; in oil) was added to a mixture consisting of 3.3 g of benzyl 3-t-butoxycarbonylaminopiperidine-1-carboxylate, 0.75 ml of methyl iodide and 20 ml of N,N-dimethylformamide in a water bath at room temperature. The mixture was stirred at room temperature for 4 hours. The reaction solution was partitioned between ethyl acetate and water, and the organic layer was washed with water and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography using 10% to 20% ethyl acetate/hexane to give an oily material (3.04 g). This whole ammount was combined with 20 ml of ethanol and 10% palladium carbon. This mixture was stirred at room temperature under a hydrogen atmosphere for five hours. After the catalyst was removed by filtration, the filtrate was concentrated to give 1.82 g of the title compound. 1H-NMR(CDCl3) delta 1.46 (s, 9H) 1.48-1.64 (m, 2H) 1.72-1.84 (m, 2H) 2.43 (dt, J=3 Hz, 12 Hz, 1H) 2.60 (t, J=12 Hz, 1H) 2.75 (s, 3H) 2.74-3.02 (m, 2H) 3.86 (br.s, 1H)

References: [1]Patent: EP1568699,2005,A1 .Location in patent: Page/Page column 42.
[2]Patent: US2004/116328,2004,A1 .

9
[ 4548-45-2 ]
[ 172478-01-2 ]
[ 1356953-52-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In tetrahydrofuran; at 20℃; for 16h;	Example 1024tert-buiy methyl(l -(5-nitropyridin-2-yl)piperidin-3-yl)carbamateTo a solution of tert-buty methyl(piperidin-3-yl)carbamate (1 .00 g, 4.67 mmol) in THF (25 mL) was added triethylamine (0.70 mL, 5.0 mmol) and 2-chloro-5-nitropyridine (500 mg, 3.1 mmol). The reaction mixture was then stirred at room temperature for 16 h, diluted with a saturated NaHC03 solution and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (silica, ethyl acetate/hexanes) afforded the desired product (1.03 g, 99%) as a yellow solid. ESI MS m/z 337 [Ci6H24 404 + H]+

References: [1]Patent: WO2012/16082,2012,A1 .Location in patent: Page/Page column 273.

10
[ 172478-01-2 ]
[ 1356953-53-1 ]

References: [1]Patent: WO2012/16082,2012,A1 .

11
[ 172478-01-2 ]
tert-butyl (trans-4-((dimethyl-d6-amino)methyl)cyclohexyl)carbamate [ No CAS ]

References: [1]Patent: WO2012/16082,2012,A1 .

12
[ 172478-01-2 ]
1-(6-bromo-4-((trans-4-((dimethyl-d6-amino)methyl)cyclohexyl)amino)quinolin-3-yl)ethanone [ No CAS ]

References: [1]Patent: WO2012/16082,2012,A1 .

13
[ 172478-01-2 ]
1-(6-(3,5-dichloro-4-hydroxyphenyl)-4-((trans-4-((dimethyl-d6-amino)methyl)cyclohexyl)amino)quinolin-3-yl)ethanone dihydrochloride [ No CAS ]

References: [1]Patent: WO2012/16082,2012,A1 .

14
[ 172478-01-2 ]
C₁₆H₂₆N₄O₂ [ No CAS ]