Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 56619-93-3 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support Online Technical Q&A

Product Details of [ 56619-93-3 ]

CAS No. :	56619-93-3
Formula :	C₁₂H₁₇NO₂
M.W :	207.27
SMILES Code :	CC(C)(C)C(NC1=CC=CC(OC)=C1)=O
MDL No. :	MFCD00662896
Boiling Point :	No data available
InChI Key :	DAFHCFQPQMYDFI-UHFFFAOYSA-N
Pubchem ID :	546358

Safety of [ 56619-93-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Calculated chemistry of [ 56619-93-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	61.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.33 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.58
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	2.7
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.49
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.	2.11
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	2.16
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.86
Solubility	0.287 mg/ml ; 0.00139 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.	-3.16
Solubility	0.144 mg/ml ; 0.000695 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	-3.74
Solubility	0.0375 mg/ml ; 0.000181 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	Yes
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.	-5.65 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	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)	1.56

Application In Synthesis of [ 56619-93-3 ]

* 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 [ 56619-93-3 ]

[ 56619-93-3 ] Synthesis Path-Downstream 1~27

1
[ 75-21-8 ]
[ 56619-93-3 ]
[ 76093-72-6 ]

Yield	Reaction Conditions	Operation in experiment
77.1%		Synthesis of N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (1b) Under the argon atmosphere, n-butyllithium (nBuLi) (2.6 M in THF, 111 mL, 289 mmol, commercial product) was slowly dropped at 0C into a tetrahydrofuran (THF) (400 mL, dehydrated, commercial product) solution of the compound 1a (30.0 g, 145 mmol). After the mixture was stirred at 0C for 2 hours, ethylene oxide (1.3 M ether solution, 175 mL, 228 mmol, commercial product) was slowly added to the mixture and stirred at 0C for 1 hour. The temperature was raised to room temperature, and then the mixture was further stirred for 2 hours. The mixture was concentrated under reduced pressure, to which a saturated ammonium chloride aqueous solution (sat. NH4Cl aq.) was added. Subsequently, the mixture was extracted with ethyl acetate (EtOAc) (100 mL * 4). The combined organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized with ethyl acetate (EtOAc), and thus N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (compound 1b) (28.1 g, 112 mmol, 77.1%) was obtained as a colorless solid. TLC Rf= 0.40 (n-hexane/EtOAc = 3/1)
77.1%		Synthesis of N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (1b) Under the argon atmosphere, n-butyllithium (nBuLi) (2.6 M in THF, 111 mL, 289 mmol, commercial product) was slowly dropped at 0 C. into a tetrahydrofuran (THF) (400 mL, dehydrated, commercial product) solution of the compound 1a (30.0 g, 145 mmol). After the mixture was stirred at 0 C. for 2 hours, ethylene oxide (1.3 M ether solution, 175 mL, 228 mmol, commercial product) was slowly added to the mixture and stirred at 0 C. for 1 hour. The temperature was raised to room temperature, and then the mixture was further stirred for 2 hours. The mixture was concentrated under reduced pressure, to which a saturated ammonium chloride aqueous solution (sat. NH4Cl aq.) was added. Subsequently, the mixture was extracted with ethyl acetate (EtOAc) (100 mL*4). The combined organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized with ethyl acetate (EtOAc), and thus N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (compound 1b) (28.1 g, 112 mmol, 77.1%) was obtained as a colorless solid. TLC Rf=0.40 (n-hexane/EtOAc=3/1)
53%		Synthesis of N-(2-(2-hydroxyethyl)-3-methoxyphenylpivalamide Into a 250 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of <strong>[56619-93-3]N-(3-methoxyphenyl)pivalamide</strong> (11.8 g, 57.00 mmol, 1.00 equiv) in THF (200 mL). To the above was added n-BuLi (60 mL) dropwise with stirring while the temperature was maintained at 0 C. in a bath of H2O/ice. The resulting solution was allowed to react, with stirring, for 2 h. To the above was added oxirane (7 mL, 1.50 equiv) dropwise with stirring while the temperature was maintained at 0 C. in a bath of H2O/ice. The resulting solution was allowed to react, with stirring, for 1 h while the temperature was maintained at 0 C. in a bath of H2O/ice. The resulting solution was allowed to react for 2 h while the temperature was maintained at room temperature. The reaction mixture was then quenched by the adding H2O. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was extracted with EtOAc and the organic layers combined. The organic phase was washed with Na2CO3. The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The final product was purified by recrystallization from DCM/hexane. This resulted in 10.5 g (53%) of N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide as a white solid.

53%		A solution of n-butyllithium in hexane (60 mL) was added dropwise to a solution of N-(3- methoxyphenyl)pivalamide (57.0 mmol) in tetrahydrofuran (200 mL) at 0 C and was maintained for 2 h. Oxirane (86 mmol) was added dropwise and the reaction mixture was maintained for 1 h at 0 C and for an additional 2 h at rt. The reaction mixture was concentrated and the residue was diluted with water (100 mL) and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were washed with saturated aqueous sodium carbonate, dried (sodium sulfate), and concentrated. The final product was purified by recrystallization (dichloromethane/cyclohexane) to provide N-(2-(2-hydroxyethyl)-3- methoxyphenyl)pivalamide in 53% yield as a white solid.
53%		Synthesis of N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide Into a 250 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of <strong>[56619-93-3]N-(3-methoxyphenyl)pivalamide</strong> (11.8 g, 57.00 mmol, 1.00 equiv) in THE (200 mL). To the above was added n-BuLi (60 mL) dropwise with stirring while the temperature was maintained at 0 C. in a bath of H2O/ice. The resulting solution was allowed to react with stirring, for 2 h. To the above was added oxirane (7 mL, 1.50 equiv) dropwise with stirring while the temperature was maintained at 0 C. in a bath of H2O/ice. The resulting solution was allowed to react with stirring, for 1 h while the temperature was maintained at 0 C. in a bath of H2O/ice. The resulting solution was allowed to react for 2 h while the temperature was maintained at room temperature. The reaction mixture was then quenched by the adding H2O. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was extracted with EtOAc and the organic layers combined. The organic phase was washed with Na2CO3. The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The final product was purified by recrystallization from DCM/hexane. This resulted in 10.5 g (53%) of N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide as a white solid.
53%		3. Synthesis of N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide; A solution of n-butyllithium in hexane (60 mL) was added dropwise to a solution of <strong>[56619-93-3]N-(3-methoxyphenyl)pivalamide</strong> (57.0 mmol) in tetrahydrofuran (200 mL) at 0 C. and was maintained for 2 h. Oxirane (86 mmol) was added dropwise and the reaction mixture was maintained for 1 h at 0 C. and for an additional 2 h at rt. The reaction mixture was concentrated and the residue was diluted with water (100 mL) and extracted with ethyl acetate (3×75 mL). The combined organic layers were washed with saturated aqueous sodium carbonate, dried (sodium sulfate), and concentrated. The final product was purified by recrystallization (dichloromethane/cyclohexane) to provide N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide in 53% yield as a white solid.
53%		3. Synthesis of A/-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide.A solution of r°-butyllithium in hexane (60 mL) was added dropwise to a solution of N-(3- methoxyphenyl)pivalamide (57.0 mmol) in tetrahydrofuran (200 mL) at 0 0C and was maintained for 2 h. Oxirane (86 mmol) was added dropwise and the reaction mixture was maintained for 1 h at 0 0C and for an additional 2 h at rt. The reaction mixture was concentrated and the residue was diluted with water (100 mL) and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were washed with saturated aqueous sodium carbonate, dried (sodium sulfate), and concentrated. The final product was purified by recrystallization(dichloromethane/cyclohexane) to provide N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide in 53% yield as a white solid.
53%	With (2-methylpropyl)lithium; In tetrahydrofuran; hexane; at 0 - 20℃;	A solution of i-butyllithium in hexane (60 mL) was added dropwise to a solution of <strong>[56619-93-3]N-(3-methoxyphenyl)pivalamide</strong> (57.0 mmol) in tetrahydrofuran (200 mL) at 0 C. and was maintained for 2 h. Oxirane (86 mmol) was added dropwise and the reaction mixture was maintained for 1 h at 0 C. and for an additional 2 h at rt. The reaction mixture was concentrated and the residue was diluted with water (100 mL) and extracted with ethyl acetate (3×75 mL). The combined organic layers were washed with saturated aqueous sodium carbonate, dried (sodium sulfate), and concentrated. The final product was purified by recrystallization (dichloromethane/cyclohexane) to provide N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide in 53% yield as a white solid.
53%		3. Synthesis of iV-(2-(2-hvdroxyethv0-3-methoxyphenyl)pivalamide.A solution of w-butyllithium in hexane (60 mL) was added dropwise to a solution of N-(3- methoxyphenyl)pivalamide (57.0 mmol) in tetrahydrofuran (200 mL) at 0 0C and was maintained for 2 h. Oxirane (86 mmol) was added dropwise and the reaction mixture was maintained for 1 h at 0 0C and for an additional 2 h at rt. The reaction mixture was concentrated and the residue was diluted with water (100 mL) and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were washed with saturated aqueous sodium carbonate, dried (sodium sulfate), and concentrated. The final product was purified by recrystallization(dichloromethane/cyclohexane) to provide N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide in 53% yield as a white solid.
53%		A solution of n-butyllithium in hexane (60 mL) was added dropwise to a solution of <strong>[56619-93-3]N-(3-methoxyphenyl)pivalamide</strong> (57.0 mmol) in tetrahydrofuran (200 mL) at 0 C. and was maintained for 2 h. Oxirane (86 mmol) was added dropwise and the reaction mixture was maintained for 1 h at 0 C. and for an additional 2 h at rt. The reaction mixture was concentrated and the residue was diluted with water (100 mL) and extracted with ethyl acetate (3*75 mL). The combined organic layers were washed with saturated aqueous sodium carbonate, dried (sodium sulfate), and concentrated. The final product was purified by recrystallization (dichloromethane/cyclohexane) to provide N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide in 53% yield as a white solid.

References: [1]Patent: EP2881397,2015,A1 .Location in patent: Paragraph 0053; 0056; 0057.
[2]Patent: US2016/303089,2016,A1 .Location in patent: Paragraph 0161; 0165; 0166; 0167.
[3]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1333 - 1335.
[4]Patent: US2008/318941,2008,A1 .Location in patent: Page/Page column 39.
[5]Patent: WO2009/23844,2009,A2 .Location in patent: Page/Page column 127-128.
[6]Patent: US2008/200471,2008,A1 .Location in patent: Page/Page column 60; 61.
[7]Patent: US2010/16297,2010,A1 .Location in patent: Page/Page column 35.
[8]Patent: WO2010/21797,2010,A1 .Location in patent: Page/Page column 92-93.
[9]Patent: US2010/29629,2010,A1 .Location in patent: Page/Page column 61.
[10]Patent: WO2010/24980,2010,A1 .Location in patent: Page/Page column 111.
[11]Patent: US2010/22581,2010,A1 .Location in patent: Page/Page column 45; 46.
[12]Angewandte Chemie - International Edition,2015,vol. 54,p. 14866 - 14870.
Angew. Chem.,2015,vol. 127,p. 15079 - 15083,5.

2
[ 56619-93-3 ]
[ 18798-64-6 ]