845267-78-9|tert-Butyl 2,4-dioxopiperidine-1-carboxylate| Ambeed

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Quality Control of [ 845267-78-9 ] Purity: 97% SDS Specification

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Product Details of [ 845267-78-9 ]

CAS No. :	845267-78-9
Formula :	C₁₀H₁₅NO₄
M.W :	213.23
SMILES Code :	C(=O)(OC(C)(C)C)N1CCC(CC1=O)=O
MDL No. :	MFCD10566071
Boiling Point :	No data available
InChI Key :	SLCAHLSQXDNQSF-UHFFFAOYSA-N
Pubchem ID :	23730999

Safety of [ 845267-78-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 845267-78-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	0
Fraction Csp3	0.7
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	56.99
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.55
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	0.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.73
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.	0.24
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	0.86
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.78

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.3
Solubility	10.6 mg/ml ; 0.0496 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.	-1.45
Solubility	7.59 mg/ml ; 0.0356 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	-1.29
Solubility	11.0 mg/ml ; 0.0514 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.	-7.22 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<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)	2.08

Application In Synthesis of [ 845267-78-9 ]

* 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 [ 845267-78-9 ]

[ 845267-78-9 ] Synthesis Path-Downstream 1~13

1
[ 845267-78-9 ]
[ 50607-30-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 3h;Product distribution / selectivity;	Boc-beta-alanine (25 g, 132 mmol), Meldrum's acid (20.9 g, 145 mmol) and 4- dimethylaminopyridine (DMAP, 24.2 g, 198 mmol) were dissolved in 700 mL of dry dichloromethane (DCM) at 00C under nitrogen atmosphere. To this solution 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 30.4 g, 158 mmol) was added. The resulting solution was allowed to reach room temperature and stirred overnight. The reaction mixture was washed (0.5 L x 4) with 5percent KHSO4 aqueous solution. The organic layer was dried over anh. Na2SO4, filtered and evaporated under vacuum, affording crude [3-(2,2-dimethyl-4,6-dioxo-[1 ,3]dioxan-5-yl)-3-oxo-propyl]- carbamic acid tert-butyl ester that was dissolved in 600 mL of ethylacetate and refluxed for 4 hours. The solvent was reduced to 150 mL under vacuum and the resulting <n="23"/>solution was allowed to crystallize at 4°C overnight. The solid was filtered and washed with cold ethyl acetate affording 18.4 g (65percent yield) of the title compound.1 H NMR (400 MHz, DMSO-D6) delta ppm 1.44 (s, 9 H) 2.44 (m, 2 H) 3.71 (m, 2 H) 4.95 (s,1 H) 11.2 (bs, 1 H). The compound thus obtained can be converted into piperidine-2,4-dione in quantitative yield by dissolving it in dichloromethane and treating with trifluoroacetic acid at room temperature for 3 hours.
94%	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 1h;	TFA (140mL) was added drop wise to a solution of fert-butyl 2,4- dioxopiperidine-l-carboxylate (I-59c: 28g, 131.45mmol) in DCM (280mL) at 0°C and the resulting reaction mass was stirred at room temperature for 1 hour. The reaction was monitored by TLC (10percent methanol in DCM). The reaction mass was concentrated under reduced pressure to afford the crude product which was dried under high vacuum and washed with ether to afford 14g of the product (94percent yield).
94%	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃;	Preparation of Intermediate piperidine-2,4-dione (I-59d) TFA (140 mL) was added drop wise to a solution of tert-butyl 2,4-dioxopiperidine-1-carboxylate (I-59c: 28 g, 131.45 mmol) in DCM (280 mL) at 0° C. and the resulting reaction mass was stirred at room temperature for 1 hour. The reaction was monitored by TLC (10percent methanol in DCM). The reaction mass was concentrated under reduced pressure to afford the crude product which was dried under high vacuum and washed with ether to afford 14 g of the product (94percent yield).

References: [1]Patent: WO2008/104475,2008,A1 .Location in patent: Page/Page column 22.
[2]Patent: WO2012/35078,2012,A1 .Location in patent: Page/Page column 144.
[3]Patent: US2014/45872,2014,A1 .Location in patent: Paragraph 0911.
[4]Journal of Medicinal Chemistry,2008,vol. 51,p. 487 - 501.
[5]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

2
[ 845267-78-9 ]
[ 3325-11-9 ]
[ 555-16-8 ]
tert-butyl 11-(4-nitrophenyl)-10-oxo-7,8,10,11-tetrahydro-1H-[1,2,3]triazolo[4′,5′:3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate [ No CAS ]