[ CAS No. 308831-94-9 ] {[proInfo.proName]}

Name: 308831-94-9|Ethyl 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate|98%
Brand: Ambeed
SKU: A624904
Rating: 94 (30 reviews)

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Cat. No.: {[proInfo.prAm]}

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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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Quality Control of [ 308831-94-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 308831-94-9 ]

SDS Specification

Alternatived Products of [ 308831-94-9 ]

Product Details of [ 308831-94-9 ]

CAS No. :	308831-94-9	MDL No. :	MFCD31806862
Formula :	C₂₄H₂₂F₂N₂O₆S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VEQKKZQAOCWPKO-UHFFFAOYSA-N
M.W :	504.50	Pubchem ID :	18324799
Synonyms :

Calculated chemistry of [ 308831-94-9 ]

Physicochemical Properties

Num. heavy atoms :	35
Num. arom. heavy atoms :	17
Fraction Csp3 :	0.25
Num. rotatable bonds :	11
Num. H-bond acceptors :	8.0
Num. H-bond donors :	0.0
Molar Refractivity :	129.53
TPSA :	129.9 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.93
Log Po/w (XLOGP3) :	5.84
Log Po/w (WLOGP) :	6.94
Log Po/w (MLOGP) :	3.82
Log Po/w (SILICOS-IT) :	4.73
Consensus Log Po/w :	5.05

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.28
Solubility :	0.000264 mg/ml ; 0.000000524 mol/l
Class :	Poorly soluble
Log S (Ali) :	-8.34
Solubility :	0.00000231 mg/ml ; 0.0000000046 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-7.55
Solubility :	0.0000144 mg/ml ; 0.0000000284 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.13

Safety of [ 308831-94-9 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P201-P202-P261-P281-P305+P351+P338-P308+P313	UN#:	2811
Hazard Statements:	H302-H315-H319-H335-H350	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 308831-94-9 ]

* 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 [ 308831-94-9 ]

[ 308831-94-9 ] Synthesis Path-Downstream 1~32

1
ethyl 2-[(ethoxycarbonyl)amino]-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate [ No CAS ]
[ 697-73-4 ]
[ 308831-94-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium iodide; potassium carbonate; In N,N-dimethyl-formamide;	Reference Example 10 Ethyl 2-[N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino]-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate To a solution of the compound obtained in Reference Example 9 (490 mg, 1.30 mol) in N,N-dimethylformamide (20 ml) were added potassium carbonate (196 mg, 1.42 mol), potassium iodide (236 mg, 1.42 mol) and 2,6-difluorobenzyl chloride (232 mg, 1.42 mmol), and the mixture was stirred at room temperature for 5 hours. This reaction mixture was concentrated and the residue was partitioned between chloroform and aqueous sodium chloride solution. The aqueous layer was extracted with chloroform. The organic extracts were combined and washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel and the amorphous powder obtained was recrystallized from methanol to give the title compound as yellow powdery crystals (520 mg, 79%). mp: 91-92 C.; 1H-NMR (300 MHz, CDCl3) delta: 1.15-1.35 (6H, m), 2.40 (3H, s), 4.15-4.29 (4H, m), 4.97 (2H, s), 6.86 (2H, t, J=7.8 Hz), 7.25-7.32 (1H, m), 7.51 (2H, d, J=8.8 Hz), 8.25 (2H, d). IR (KBr): 1717, 1597, 1524, 1475, 1392, 1348 cm-1.
79%	With potassium carbonate; potassium iodide; In DMF (N,N-dimethyl-formamide); at 15 - 25℃; for 5.0h;	To a solution of the compound obtained in Reference Example 9 (490 mg, 1.30 mol) in N,N-dimethylformamide (20 ml) were added potassium carbonate (196 mg, 1.42 mol), potassium iodide (236 mg, 1.42 mol) and 2,6-difluorobenzyl chloride (232 mg, 1.42 mmol), and the mixture was stirred at room temperature for 5 hours. This reaction mixture was concentrated and the residue was partitioned between chloroform and aqueous sodium chloride solution. The aqueous layer was extracted with chloroform. The organic extracts were combined and washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel and the amorphous powder obtained was recrystallized from methanol to give the title compound as yellow powdery crystals (520 mg, 79%). mp: 91-92 C. 1H-NMR (300 MHz, CDCl3) delta: 1.15-1.35 (6H, m), 2.40 (3H, s), 4.15-4.29 (4H, m), 4.97 (2H, s), 6.86 (2H, t, J=7.8 Hz), 7.25-7.32 (1H, m), 7.51 (2H, d, J=8.8 Hz), 8.25 (2H, d). IR (KBr): 1717, 1597, 1524, 1475, 1392, 1348 cm-1.

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4998 - 5012
[2]Patent: US6297379,2001,B1
[3]Patent: US6340686,2002,B1 .Location in patent: Page column 23-24

2
[ 308831-94-9 ]
[ 308831-95-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 100℃; for 2.0h;	A mixture of the compound obtained in Reference Example 10 (20 g, 39.64 mol), N-bromosuccinimide (7.76 g, 43.60 mol), alpha,alpha'-azobisisobutyronitrile (0.72 g, 4.36 mol) and carbon tetrachloride (300 ml) was stirred at 100 C. for 2 hours.. After cooling, this reaction mixture was washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure.. The residue was chromatographed on silica gel to give the title compound as amorphous powder (23 g, 100%). mp: 105-108 C. 1H-NMR (300 MHz, CDCl3) delta: 1.15-1.39 (6H, m), 4.09-4.39 (4H, m), 4.71 (2H, s), 4.99 (2H, s), 6.86 (2H, t, J=7.8 Hz), 7.22-7.32 (1H, m), 7.72 (2H, d, J=8.0 Hz), 8.32 (2H, d, J=8.0 Hz). IR (KBr): 1725, 1628, 1522, 1475, 1379, 1348 cm-1. FAB-Mass m/z 582 (MH+).

Reference： [1]Patent: US6340686,2002,B1 .Location in patent: Page column 24
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 4998 - 5012

3
[ 308831-94-9 ]
[ 34241-39-9 ]
[ 308831-95-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide; In tetrachloromethane;	Reference Example 11 Ethyl 4-bromomethyl-2-[N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino]-5-(4-nitrophenyl)thiophene-3-carboxylate A mixture of the compound obtained in Reference Example 10 (20 g, 39.64 mol), N-bromosuccinimide (7.76 g, 43.60 mol), alpha,alpha'-azobisisobutyronitrile (0.72 g, 4.36 mol) and carbon tetrachloride (300 ml) was stirred at 100 C. for 2 hours. After cooling, this reaction mixture was washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel to give the title compound as amorphous powder (23 g, 100%). mp: 105-108 C.; 1H-NMR (300 MHz, CDCl3) delta: 1.15-1.39 (6H, m), 4.09-4.39 (4H, m), 4.71 (2H, s), 4.99 (2H, s), 6.86 (2H, t, J=7.8 Hz), 7.22-7.32 (1H, m), 7.72 (2H, d, J=8.0 Hz), 8.32 (2H, d, J=8.0 Hz). IR (KBr): 1725, 1628, 1522, 1475, 1379, 1348 cm-1. FAB-Mass m/z 582 (MH+).

Reference： [1]Patent: US6297379,2001,B1

4
[ 308831-94-9 ]
[ 308832-01-1 ]