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Quality Control of [ 80-73-9 ] Purity: 98% SDS Specification

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Product Details of [ 80-73-9 ]

CAS No. :	80-73-9
Formula :	C₅H₁₀N₂O
M.W :	114.15
SMILES Code :	O=C1N(C)CCN1C
MDL No. :	MFCD00003188
InChI Key :	CYSGHNMQYZDMIA-UHFFFAOYSA-N
Pubchem ID :	6661

Safety of [ 80-73-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H318-H361-H402
Precautionary Statements:	P201-P202-P264-P270-P273-P280-P301+P312+P330-P305+P351+P338+P310-P308+P313-P405-P501

Computational Chemistry of [ 80-73-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	0
Fraction Csp3	0.8
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	38.25
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	23.55 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.51
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	-0.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.78
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.	0.03
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	-0.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.24
Solubility	65.8 mg/ml ; 0.577 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.	0.46
Solubility	331.0 mg/ml ; 2.9 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	0.01
Solubility	117.0 mg/ml ; 1.03 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	Low
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.	-7.34 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)	1.34

Application In Synthesis of [ 80-73-9 ]

* 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 [ 80-73-9 ]

[ 80-73-9 ] Synthesis Path-Downstream 1~12

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[ 80-73-9 ]
[ 79-37-8 ]
[ 37091-73-9 ]

References: [1]Tetrahedron,1986,vol. 42,p. 6645 - 6656.

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[ 37091-73-9 ]

Yield	Reaction Conditions	Operation in experiment
96.6%	With phosgene; In tetrachloromethane; at 5 - 50℃; for 5.5h;	For 1000 ml three port in the reaction bottle, by adding 1,3-dimethyl-2-imidazolidinone (34.2 g, 0.3 mol), carbon tetrachloride (400 ml), stirring slowly dropwise solid phosgene carbon tetrachloride solution (containing solid phosgene 30 g, 0.1 mole, carbon tetrachloride 100 ml), the reaction mixture is kept below 5 C, violent mixing 0.5 hours, the reaction at room temperature 1 hour, heating to 50 C, maintain 4 hours. To be the reaction product is cooled to room temperature, filter, a small amount of carbon tetrachloride washing, get a pure white crystalline product chloropivaloyl 1,3-dimethyl-2-chlorotrifluoromethylbenzene imidazoline 49 g, yield of 96.6%,
70.1%	With oxalyl dichloride; In benzene; at 20℃; for 5h;Inert atmosphere;	Under an inert atmosphere, 1,3-Dimethyl-2-imidazolidinone (7.0 mL, 64 mmol) was dissolved in anhydrous benzene (25 mL). To this oxalyl chloride (7.2 mL, 80 mmol) was added, and the solution was refluxed for 5 hours, and allowed to sit at room temperature overnight. The solution was filtered quickly to give 2-chloro-1,3-dimethylimidazolinium chloride (7.5815 g, 44.85 mmol) in 70.1% yield.
53%	With Phthaloyl dichloride; at 140℃; for 5h;	1,3-dimethyl-2-imidazolidinone 3.50g (30.7 mmol), and the mixture was heated for 5 hours and stirred at 140 of chloride phthalic acid 6.54g (32.4 mmol). After cooling, the crystal upon addition of 1,4-dioxane 25mL precipitated, filtered with a glass filter, washed twice with 1,4-dioxane 10 mL, washed once with ether 5 mL, and dried under vacuum. To give 2-chloro-1,3-dimethyl imidazolium chloride 2.72g (53% yield).

	With oxalyl dichloride; In chloroform; for 20h;Reflux; Inert atmosphere; Schlenk technique;	To a solution of 1,3-dimethyl-2-imidazolidinone (1.0 mL, 9.3 mmol) dissolved in dry CHCl3 (20 mL) was added oxalyl chloride (3.9 mL,44.7 mmol) dropwise. The yellow solution was stirred at reflux for 20 h. The solvent was removed under vacuum. The remaining solid was washed twice with Et2O
	With oxalyl dichloride; In toluene; at 80℃; for 12h;Inert atmosphere;	General procedure: N,N?-Disubstituted cyclic urea (6 mmol) was dissolved in toluene (50 mL) and oxalyl chloride (7.6 g, 5.2 mL, 60 mmol) was added. The resulting mixture was stirred at 80 C for 12 h. The white precipitate was then filtered off under an inert atmosphere, washed with anhydrous Et2O, and dried in vacuo to give the pure chloride as a white solid.
	With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 6h;Inert atmosphere;	General procedure: A solution of urea (50mmol) in dry CH2Cl2 (10mL) was added dropwise at 0C under an Argon atmosphere to a solution of freshly distilled oxalyl chloride (55 mmoL) in dry CH2Cl2 (25ml). The reaction mixture was allowed to reach rt. and was stirred at rt 6h. The solvent was then evaporated under reduced pressure to afford a brown solid which was washed with dry Et2O (4×20mL) to give a white solid.
	With oxalyl dichloride; In toluene; at 60℃; for 20h;Inert atmosphere; Cooling with ice;	General procedure: 1 ml urea derivatives dissolved in 400 ml toluene. 1.2 mol oxalyl chloride dissolved in toluene and then instilled to previous system in ice bath, protected by nitrogen and with strongly stirred. Then stirred in room temperature for 2h and heated in 60 for 20h. The mixture was cooled and filtered in reduced pressure, washed by ethyl acetate to get white solid. Needle-like crystal was harvested with 95%-97% yields after crystallization via ethyl acetate and acetonitrile.

References: [1]Patent: CN105367478,2016,A .Location in patent: Paragraph 0021; 0027; 0028.
[2]European Journal of Inorganic Chemistry,2005,p. 3815 - 3824.
[3]Chemistry - A European Journal,2016,vol. 22,p. 16187 - 16199.
[4]Synthesis,2009,p. 2267 - 2277.
[5]Helvetica Chimica Acta,1985,vol. 68,p. 1543 - 1556.
[6]Journal of Organic Chemistry,2018,vol. 83,p. 13051 - 13062.
[7]Tetrahedron Letters,2011,vol. 52,p. 3723 - 3725.
[8]Angewandte Chemie - International Edition,2014,vol. 53,p. 11907 - 11911.
Angew. Chem.,2014,vol. 126,p. 12101 - 12105,5.
[9]Journal of the American Chemical Society,2006,vol. 128,p. 14185 - 14191.
[10]Patent: JP5782331,2015,B2 .Location in patent: Paragraph 0031.
[11]Synlett,2003,p. 369 - 371.
[12]Chemical Communications,2002,p. 1618 - 1619.
[13]Synthesis,2008,p. 917 - 920.
[14]Journal of the American Chemical Society,2009,vol. 131,p. 2882 - 2892.
[15]European Journal of Inorganic Chemistry,2011,p. 1302 - 1314.
[16]Inorganica Chimica Acta,2011,vol. 374,p. 546 - 557.
[17]European Journal of Inorganic Chemistry,2012,p. 4833 - 4845.
[18]European Journal of Inorganic Chemistry,2013,p. 163 - 171.
[19]Tetrahedron,2013,vol. 69,p. 8943 - 8951.
[20]Organic Letters,2014,vol. 16,p. 2790 - 2793.
[21]Dalton Transactions,2016,vol. 45,p. 16966 - 16983.
[22]Angewandte Chemie - International Edition,2017,vol. 56,p. 3360 - 3363.
Angew. Chem.,2017,vol. 129,p. 3408 - 3412,5.
[23]Organometallics,2018,vol. 37,p. 1172 - 1180.
[24]Journal of Physical Organic Chemistry,2018,vol. 31.
[25]Journal of Molecular Liquids,2019,vol. 277,p. 280 - 289.
[26]Tetrahedron Letters,2013,vol. 54,p. 6959 - 6963.

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[ 80-73-9 ]
[ 75-44-5 ]
[ 37091-73-9 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 8790 - 8797.

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[ 80-73-9 ]
[ 32618-85-2 ]
[ 1003-03-8 ]
[ 221043-21-6 ]