[ CAS No. 431980-38-0 ] {[proInfo.proName]}

Name: 431980-38-0|N-(2-Methoxyphenyl)-2-((4-nitrophenyl)thio)benzamide|98%
Brand: Ambeed
SKU: A145644
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Quality Control of [ 431980-38-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 431980-38-0 ]

SDS Specification

Alternatived Products of [ 431980-38-0 ]

Product Details of [ 431980-38-0 ]

CAS No. :	431980-38-0	MDL No. :	MFCD03142961
Formula :	C₂₀H₁₆N₂O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JKNUDHUHXMELIJ-UHFFFAOYSA-N
M.W :	380.42	Pubchem ID :	1317590
Synonyms :

Calculated chemistry of [ 431980-38-0 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.05
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	106.54
TPSA :	109.45 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.68
Log Po/w (XLOGP3) :	4.63
Log Po/w (WLOGP) :	4.82
Log Po/w (MLOGP) :	3.41
Log Po/w (SILICOS-IT) :	2.15
Consensus Log Po/w :	3.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.15
Solubility :	0.00271 mg/ml ; 0.00000713 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.65
Solubility :	0.0000843 mg/ml ; 0.000000222 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.99
Solubility :	0.0000391 mg/ml ; 0.000000103 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.64

Safety of [ 431980-38-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 431980-38-0 ]

* 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.

Upstream synthesis route of [ 431980-38-0 ]
Downstream synthetic route of [ 431980-38-0 ]

[ 431980-38-0 ] Synthesis Path-Upstream 1~10

1
[ 36684-47-6 ]
[ 1849-36-1 ]
[ 431980-38-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; ethylene glycol In isopropyl alcohol at 20℃; for 1 h; microwave irradiation	Method A: Synthesis of 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) Vif inhibitor 1 was synthesized using the procedure outlined in Scheme 9. The key step in this reaction scheme is the copper catalyzed coupling reaction of 2-iodo-N-(2-methoxyphenyl)benzamide 3 with 4-nitrothiophenol 4 by microwave irradiation. The intermediate compound 3 was obtained in excellent yield by the reaction of 2-methoxyaniline 5 with 2-iodobezoyl chloride 2. Scheme 9: (a) Et₃N, CH₂Cl₂, 0° C. to r. t. overnight, 98percent; (b) K₂CO₃, Cu(I)I (cat.), HOCH₂CH₂OH, 2-propanol, microwave-150 W, 80° C., 30 min (2.x.), 63percent. 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) 2-Iodo-N-(2-methoxyphenyl)benzamide 3 (0.355 g, 1.0 mmol), Cu(I) iodide (20 mg, 0.1 mmol), K₂CO₃(0.276 g, 2.0 mmol), and 4-nitrothiophenol (0.155 g, 1 mmol) were added to a 10 mL reaction vessel with Teflon-lined septum. The tube was evacuated and backfilled with dry N₂(3 cycles). Ethylene glycol (0.1 mL, 2.0 mmol) and 2-propanol (1 mL) were added by syringe at room temperature. The reaction vessel was heated in a microwave reactor (CEM, Explorer) at 80° C. and 150 W power for 30 min (2.x.). The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 10 mL) was added; the reaction mixture was filtered and concentrated. The crude product was purified by flash column chromatography on silica, eluting with 20percent EtOAc in hexanes. This procedure provided 2-(4-nitrophenylthio)-N-(2-methoxyphenyl)benzamide 1 as pale yellow crystalline solid (0.24 g, 63percent); ¹H NMR (400 MHz, CDCl₃) δ 8.40 (d, J=8.0 Hz, 1H), 8.39 (s, 1H, overlapping signal), 8.05 (ddd, J=9.2, 2.4, 1.6 Hz, 2H), 7.77 (dd, J=6.4, 2.4 Hz, 1H), 7.56-7.49 (m, 3H), 7.29-7.25 (m, 2H), 7.06 (ddd, J=9.2, 7.6, 1.6 Hz, 1H), 6.95 (dt, J=8.8, 0.8, 1.2 Hz, 1H), 6.85 (dd, J=8.0, 0.8 Hz, 1H), 3.78 (s, 3H); ¹³C NMR (100 MHz, CDCl₃) δ 165.44, 148.22, 146.87, 146.15, 140.63, 135.76, 131.66, 130.09, 129.87, 129.49, 128.79 (2C), 127.54, 124.54, 124.35 (2C), 121.37, 120.05, 110.19, 55.88; MS (ESI): m/z 402.99 (M+Na)⁺.

Reference： [1] Patent: US2007/99919, 2007, A1, . Location in patent: Page/Page column 26; 27
[2] ChemMedChem, 2012, vol. 7, # 7, p. 1217 - 1229

2
[ 20904-30-7 ]
[ 90-04-0 ]
[ 431980-38-0 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 6, p. 465 - 469

3
[ 96198-56-0 ]
[ 90-04-0 ]
[ 431980-38-0 ]

Reference： [1] Patent: US2007/99919, 2007, A1, . Location in patent: Page/Page column 27; 28
[2] ChemMedChem, 2012, vol. 7, # 7, p. 1217 - 1229

4
[ 96198-56-0 ]
[ 431980-38-0 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 6, p. 465 - 469

5
[ 147-93-3 ]
[ 431980-38-0 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 6, p. 465 - 469

6
[ 350-46-9 ]
[ 431980-38-0 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 6, p. 465 - 469

7
[ 636-98-6 ]
[ 431980-38-0 ]

Reference： [1] ChemMedChem, 2012, vol. 7, # 7, p. 1217 - 1229

8
[ 20904-30-7 ]
[ 431980-38-0 ]

Reference： [1] ChemMedChem, 2012, vol. 7, # 7, p. 1217 - 1229

9
[ 20904-31-8 ]
[ 431980-38-0 ]

Reference： [1] ChemMedChem, 2012, vol. 7, # 7, p. 1217 - 1229

10
[ 4892-02-8 ]
[ 431980-38-0 ]

Reference： [1] ChemMedChem, 2012, vol. 7, # 7, p. 1217 - 1229

[ 431980-38-0 ] Synthesis Path-Downstream 1~13

1
[ 96198-56-0 ]
[ 90-04-0 ]
[ 431980-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;Product distribution / selectivity;	Method B: Synthesis of 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) Vif inhibitor 1 and a Vif inhibitor 1-analog was synthesized according procedure outlined in Scheme 10. The key step in the reaction scheme is the copper catalyzed coupling reaction of substituted iodobenzenes 6 with methyl thiosalicylate 7 under microwave irradiations. The resulting esters 8 were hydrolyzed to obtain the acids 9 in excellent yields. Treatment of the acids 9 with oxalyl chloride and the reaction of the resulting acid chlorides with o-anisidine 11 provided 2-(4-nitrophenylthio)-N-(2-methoxyphenyl)benzamide 1 and 2-(2-chloro-4-nitrophenylthio)-N-(2-methoxyphenyl)benzamide 12b. Reaction of the acid chlorides 9 with various other amines could provide analogs of Vif inhibitor 1. Scheme 10: (a) K2CO3, Cu(I)I (cat.), 1,2-DME, microwave (150 Wt power), 80 C., 30 min (2×); (b) Ba(OH)2.8H2O, MeOH, 80 C., 2 h; (c) (OCOCl)2, CH2Cl2, r. t, 4 h; (d) Et3N, CH2Cl2, 0 C. to r. t. overnight.; General Procedure for the Amide Coupling To a solution of benzoic acid 9 (1 mmol) in dry CH2Cl2 (10 mL) was added oxalyl chloride (5 mmol) followed by a drop of dimethylformamide. The mixture was stirred at room temperature for 4 hours. Solvents were removed under reduced pressure and the residue was dried under high vacuum to give acid chloride 10 as yellow solid. A solution of amine (1 mmol) in dry CH2Cl2 (5 mL) under nitrogen atmosphere was cooled to 0 C. and Et3N (2.2 mmol) was added followed by the addition of the above acid chloride solution in CH2Cl2 (5 mL). The resulting mixture was allowed to warm to room temperature and stirred overnight. It was diluted with CH2Cl2 (20 mL), washed with H2O and saturated aqueous NaCl solution, dried (Na2SO4) and evaporated to yield a yellow solid. The product was purified by flash chromatography on silica.; 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide 1b Above general procedure provided 2-(4-nitrophenylthio)-N-(2-methoxyphenyl)benzamide 12 as pale yellow crystalline solid in 90% yield. Analytical data is identical to that of 1 made according to Method A.

Reference： [1]Patent: US2007/99919,2007,A1 .Location in patent: Page/Page column 27; 28
[2]ChemMedChem,2012,vol. 7,p. 1217 - 1229

2
[ 36684-47-6 ]
[ 1849-36-1 ]
[ 431980-38-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; ethylene glycol;copper(l) iodide; In isopropyl alcohol; at 20℃; for 1h;microwave irradiation;Product distribution / selectivity;	Method A: Synthesis of 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) Vif inhibitor 1 was synthesized using the procedure outlined in Scheme 9. The key step in this reaction scheme is the copper catalyzed coupling reaction of 2-iodo-N-(2-methoxyphenyl)benzamide 3 with 4-nitrothiophenol 4 by microwave irradiation. The intermediate compound 3 was obtained in excellent yield by the reaction of 2-methoxyaniline 5 with 2-iodobezoyl chloride 2. Scheme 9: (a) Et3N, CH2Cl2, 0 C. to r. t. overnight, 98%; (b) K2CO3, Cu(I)I (cat.), HOCH2CH2OH, 2-propanol, microwave-150 W, 80 C., 30 min (2×), 63%. 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) 2-Iodo-N-(2-methoxyphenyl)benzamide 3 (0.355 g, 1.0 mmol), Cu(I) iodide (20 mg, 0.1 mmol), K2CO3 (0.276 g, 2.0 mmol), and 4-nitrothiophenol (0.155 g, 1 mmol) were added to a 10 mL reaction vessel with Teflon-lined septum. The tube was evacuated and backfilled with dry N2 (3 cycles). Ethylene glycol (0.1 mL, 2.0 mmol) and 2-propanol (1 mL) were added by syringe at room temperature. The reaction vessel was heated in a microwave reactor (CEM, Explorer) at 80 C. and 150 W power for 30 min (2×). The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 10 mL) was added; the reaction mixture was filtered and concentrated. The crude product was purified by flash column chromatography on silica, eluting with 20% EtOAc in hexanes. This procedure provided 2-(4-nitrophenylthio)-N-(2-methoxyphenyl)benzamide 1 as pale yellow crystalline solid (0.24 g, 63%); 1H NMR (400 MHz, CDCl3) delta 8.40 (d, J=8.0 Hz, 1H), 8.39 (s, 1H, overlapping signal), 8.05 (ddd, J=9.2, 2.4, 1.6 Hz, 2H), 7.77 (dd, J=6.4, 2.4 Hz, 1H), 7.56-7.49 (m, 3H), 7.29-7.25 (m, 2H), 7.06 (ddd, J=9.2, 7.6, 1.6 Hz, 1H), 6.95 (dt, J=8.8, 0.8, 1.2 Hz, 1H), 6.85 (dd, J=8.0, 0.8 Hz, 1H), 3.78 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 165.44, 148.22, 146.87, 146.15, 140.63, 135.76, 131.66, 130.09, 129.87, 129.49, 128.79 (2C), 127.54, 124.54, 124.35 (2C), 121.37, 120.05, 110.19, 55.88; MS (ESI): m/z 402.99 (M+Na)+.

Reference： [1]Patent: US2007/99919,2007,A1 .Location in patent: Page/Page column 26; 27
[2]ChemMedChem,2012,vol. 7,p. 1217 - 1229

3
[ 636-98-6 ]
[ 431980-38-0 ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1217 - 1229

4
[ 431980-38-0 ]
[ 934670-77-6 ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1217 - 1229

5
[ 20904-30-7 ]
[ 431980-38-0 ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1217 - 1229

6
[ 20904-31-8 ]
[ 431980-38-0 ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1217 - 1229

7
[ 4892-02-8 ]
[ 431980-38-0 ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1217 - 1229

8
[ 431980-38-0 ]
[ 692290-42-9 ]