28121-73-5|8-Cbz-2,4-dioxo-1,3,8-triazaspiro[4.5]decane| Ambeed

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Quality Control of [ 28121-73-5 ] Purity: 95% SDS Specification

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Product Details of [ 28121-73-5 ]

CAS No. :	28121-73-5
Formula :	C₁₅H₁₇N₃O₄
M.W :	303.31
SMILES Code :	O=C(N(CC1)CCC1(NC(N2)=O)C2=O)OCC3=CC=CC=C3
MDL No. :	MFCD18263009
InChI Key :	HGOPYEWWZGZVJI-UHFFFAOYSA-N
Pubchem ID :	10425057

Safety of [ 28121-73-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 28121-73-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	22
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	88.38
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	87.74 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.94
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	0.7
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.3
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.	0.54
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	0.72
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.72

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.1
Solubility	2.41 mg/ml ; 0.00795 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.	-2.12
Solubility	2.3 mg/ml ; 0.00758 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	-3.62
Solubility	0.0721 mg/ml ; 0.000238 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	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.	-7.65 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	1.0 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<0.0
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)	3.4

Application In Synthesis of [ 28121-73-5 ]

* 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 [ 28121-73-5 ]

[ 28121-73-5 ] Synthesis Path-Downstream 1~26

1
[ 19099-93-5 ]
[ 151-50-8 ]
[ 28121-73-5 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

2
[ 100-39-0 ]
[ 28121-73-5 ]
[ 169206-61-5 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

3
[ 151-50-8 ]
[ 28121-73-5 ]

Yield	Reaction Conditions	Operation in experiment
86%		To a solution of benzyl-oxo piperidone carboxylate (25 g, 107ramoi) in MeOH (1 lOmL) at room temperature in a pressure bottle, ammonium carbonate (20,5 g, 2I4mmoi) asid 140 niL water were added. The mixture was stirred until ail solid was dissolved, Potassium cyanide (13.9 g, 214mmol) was added. The tube was sealed and stirred at room temperature for 90hr. The resulting white solid was filtered and washed with water. Dried and collected white solid. Yield: 28.0 g (86%)

References: [1]Patent: WO2008/14311,2008,A2 .Location in patent: Page/Page column 145.

4
[ 24424-99-5 ]
[ 28121-73-5 ]
[ 1005187-65-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine;dmap; In 1,2-dimethoxyethane; at 20℃;	A mixture of A-2 (6.07g, 20 rnmol), dk-butyl dicarbonate (1.7.4 g, BOmrnol),triethylamine (3.0 mL, 20mmol) and DMAP (30 mg) in dry DME (200ml) was stirred at room temperature over night. The solvent was removed. Solid was filtered and washed with diethyl ether to yield white solid, Yield: 8.5 g (84%)

References: [1]Patent: WO2008/14311,2008,A2 .Location in patent: Page/Page column 145.

5
[ 28121-73-5 ]
[ 685873-14-7 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

6
[ 28121-73-5 ]
[ 169206-62-6 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

7
[ 28121-73-5 ]
[ 169206-64-8 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

8
[ 28121-73-5 ]
[ 169206-63-7 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

9
[ 28121-73-5 ]
3-benzyl-8-<2-(5-fluoro-1H-indol-3-yl)ethyl>-1,3,8-triazaspiro<4.5>decan-2-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

10
[ 28121-73-5 ]
3-benzyl-8-<2-(5-fluoro-1H-indol-3-yl)ethyl>-1,3,8-triazaspiro<4.5>decane-2,4-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3772 - 3779.

11
[ 461-72-3 ]
[ 144-55-8 ]
[ 106412-35-5 ]
[ 28121-73-5 ]
[ 13625-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; acetic acid;palladium-carbon; In ethanol;	Step A Preparation of 1,3,8-triaza-spiro[4.5]decan-2,4-dione To a solution of 14.6 g (48.1 mmol) <strong>[28121-73-5]benzyl 2,4-dioxo-1,3,8-triaza-spiro[4.5]decan-8-carboxylate</strong> (prepared from N-(benzyloxycarbonyl)piperidone by the method from J. Med. Chem. 1995, 38, 3772) in 250 ml dry ethanol were added 500 mg 10% Pd/C, and the mixture was filled into an autoclave. After stirring at 60 C. and 10 atm of hydrogen for 3 h no starting hydantoin could be detected by TLC. A precipitate had been formed which was redissolved by addition of 100 ml acetic acid. The catalyst was removed by filtration and the solution was concentrated in vacuo. Aqueous sodium bicarbonate solution was added until the mixture became a clear solution, and the title compound precipitated in two crops upon concentration in vacuo. total yield: 8.1 g (99%), white powder, m.p. 303-304 C. (dec.)

References: [1]Patent: US6291469,2001,B1 .

12
[ 28121-73-5 ]
[ 74-88-4 ]
benzyl-3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		To a solution of benzyl-2,4-dioxo-1,3,8-triazaspiro[4.5)decane-8-carboxylate (3.03 g, 10 mmol) in N,N dimethylformamide (20 ml), was added potassiumcarbonate (2.76 g, 20 mmol). After stirringfor 15 5 minutes, iodomethane (1.42 g, 10 mmol) was added. Beforequenching with ice-water(10 ml), the resulting mixturewas stirred at room temperature overnight. The mixturewas extracted with dichloromethane (3 x150 mL). The combined organiclayers were dried over anhydroussodium sulfate andconcentrated under reducedpressure. The residuewas purified by silica gel column chromatographyeluting with dichloromethane: methanol=50:1) to afford benzyl-3-methyl-2,4-dioxo-1,3,8-10 triazaspiro[4.5]decane-8-carboxylate asa white solid (1 0 g, 32%). LCMS (ESI): m/z = 318.1 [M+Ht1H-NMR (300 MHz, CDCh):5= 1.57 (m, 2H), 1.70-1.85 (m, 2H), 2.84 (s, 3H), 3.24 (s, 2H), 3.84-3.90(m, 2H), 5.10 (s, 2H), 7.29-7.45(m, 5H), 8.81 (s, 1H).

References: [1]Patent: WO2015/154023,2015,A1 .Location in patent: Page/Page column 80; 81.

13
[ 28121-73-5 ]
(R)-2-fluoro-N-(1-(1-((3-methoxycyclobutyl)methyl)-3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl)-3-methyl-1-oxobutan-2-yl)-5-(trifluoromethyl)benzamide [ No CAS ]