[ CAS No. 3441-01-8 ] {[proInfo.proName]}

Name: 3441-01-8|3-Cyanobenzamide|97%
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Quality Control of [ 3441-01-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3441-01-8 ]

SDS Specification

Alternatived Products of [ 3441-01-8 ]

Product Details of [ 3441-01-8 ]

CAS No. :	3441-01-8	MDL No. :	MFCD00017574
Formula :	C₈H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PAQVSWFCADWSLB-UHFFFAOYSA-N
M.W :	146.15	Pubchem ID :	76974
Synonyms :

Calculated chemistry of [ 3441-01-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.25
TPSA :	66.88 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.98
Log Po/w (XLOGP3) :	0.52
Log Po/w (WLOGP) :	0.66
Log Po/w (MLOGP) :	0.56
Log Po/w (SILICOS-IT) :	0.95
Consensus Log Po/w :	0.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.41
Solubility :	5.67 mg/ml ; 0.0388 mol/l
Class :	Very soluble
Log S (Ali) :	-1.5
Solubility :	4.67 mg/ml ; 0.032 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.05
Solubility :	1.3 mg/ml ; 0.00889 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 3441-01-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3441-01-8 ]

* 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 [ 3441-01-8 ]

[ 3441-01-8 ] Synthesis Path-Downstream 1~34

1
[ 626-17-5 ]
[ 3441-01-8 ]

Reference： [1]ChemSusChem,2012,vol. 5,p. 1392 - 1396
[2]Journal of Organic Chemistry,2013,vol. 78,p. 11956 - 11961
[3]ChemSusChem,2011,vol. 4,p. 104 - 111
[4]Advanced Synthesis and Catalysis,2016,vol. 358,p. 2889 - 2894
[5]New Journal of Chemistry,2013,vol. 37,p. 2987 - 2990
[6]Chemische Berichte,1959,vol. 92,p. 2616,2619
[7]Journal of Molecular Structure,2003,vol. 644,p. 13 - 21
[8]Synthetic Communications,2013,vol. 43,p. 2867 - 2875

2
[ 1740-57-4 ]
[ 3441-01-8 ]

Reference： [1]Chemische Berichte,1965,vol. 98,p. 2966 - 2984

3
[ 626-17-5 ]
[ 1877-72-1 ]
[ 3441-01-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1679 - 1688

Yield	Reaction Conditions	Operation in experiment
93%	With tetrabutylammomium bromide; ammonia; caesium carbonate; In water; for 0.333333h;Microwave irradiation;	General procedure: 1 mmol of benzoic acid, 3 ml of 25-28percent aqueous ammonia, and cesium carbonate were added to a microwave reactor.0.2 mmol and 0.01 mmolTetrabutylammonium bromide was reacted at a microwave power of 120 W for 20 min.Extracted with ethyl acetate, concentrated under reduced pressure, and the product was recrystallized from ethanol.A white solid was obtained in 97percent yield.
		Preparation 80 3-(Aminomethyl)benzamide The nitrile from Preparation 79 (6.4 g, 43.8 mmol) was suspended in acetic acid (60 ml) and 10percent palladium on carbon (100 mg) was added.

5
ethyl ester of/the/ 3-cyano-benzoic acid [ No CAS ]
[ 3441-01-8 ]

Reference： [1]Chemische Berichte,1887,vol. 20,p. 521

6
methyl ester of/the/ 3-cyano-benzoic acid [ No CAS ]
[ 3441-01-8 ]

Reference： [1]Chemische Berichte,1887,vol. 20,p. 521

7
1',2',3',4',5',6'-hexahydro-2'H-[2,4'-bipyridine] N-oxide hydrochloride [ No CAS ]
[ 50-00-0 ]
[ 3441-01-8 ]
2-(1-[(3-cyanobenzoyl)amino]methyl}piperidin-4-yl)pyridinium N-oxide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7450 - 7465

8
[ 108-38-3 ]
[ 626-17-5 ]
[ 3441-01-8 ]
[ 620-22-4 ]

Reference： [1]Patent: EP1193247,2002,A2 .Location in patent: Page 5-6

9
[ 3441-01-8 ]
3-(aminocarbonothionyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen sulfide; triethylamine; In ethanol; at 20℃; for 96h;	ii) Production of 3-(aminocarbonothionyl)benzamide <strong>[3441-01-8]3-Cyanobenzamide</strong> (4.67 g) was suspended in a mixture of ethanol (500 ml) and triethylamine (1.0 ml), and hydrogen sulfide gas was blown in at room temperature for 30 min. The mixture was stirred at room temperature for 4 days and the solvent was evaporated under reduced pressure. The residue was washed with a mixture of ethanol-ethyl acetate to give the title compound (5.70 g) as a pale-yellow powder. 1H-NMR (DMSO-d6)delta: 7.40-7.56 (2H, m), 7.91-8.08 (3H, m), 8.32 (1H, t, J= 1.8 Hz), 9.58 (1H, brs), 9.98 (1H, brs). IR (KBr): 3358, 3160, 1659, 1636, 1418 cm-1.

Reference： [1]Patent: EP1348706,2003,A1 .Location in patent: Page/Page column 53-54

10
[ 1711-11-1 ]
[ 3441-01-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In dichloromethane;	Preparation 79 3-Cyanobenzamide 0.88 Ammonia solution (30 ml) was slowly added to a solution of 3-cyanobenzoyl chloride (10 g, 60.3 mmol) in dichloromethane (100 ml) at 0° C. under nitrogen and the reaction was stirred for 20 minutes. The mixture was filtered and the solid was washed with water (50 ml) then diethylether (50 ml), azeotroped with toluene and dried in vacuo to provide the title compound (9 g) as a white solid. 1H NMR (400 MHz, CD3OD): delta=7.62 (m, 1H), 7.86 (m, 1H), 8.12 (m, 1H), 8.18 (s, 1H).
	With ammonia; water; In tetrahydrofuran; at 5℃; for 1h;	i) Production of 3-cyanobenzamide A mixture of 28percent aqueous ammonia (20 ml) and THF (30 ml) was cooled to 5C and 3-cyanobenzoyl chloride (1.45 g) was slowly added. The mixture was stirred for one hr. and the reaction mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was recrystallized from ethyl acetate to give the title compound (802 mg) as colorless needle crystals. 1H-NMR (CDCl3+CD3OD)delta: 7.61 (1H, t, J= 7.8 Hz), 7.82 (1H, dt, J= 7.8, 1.4 Hz), 8.13 (1H, dt, J= 7.8, 1.4 Hz), 8.21 (1H, t, J= 1.4 Hz). IR (KBr): 3420, 3160, 2232, 1705, 1397 cm-1.

Reference： [1]Patent: US2003/100554,2003,A1
[2]Patent: EP1348706,2003,A1 .Location in patent: Page/Page column 53

11
[ 3441-01-8 ]
[ 1877-72-1 ]

Yield	Reaction Conditions	Operation in experiment
94%		The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 4.78 g of m-cyanobenzoic acid (yield 94percent, based on <strong>[3441-01-8]m-cyanobenzamide</strong>). The m-cyanobenzoic acid obtained had a purity of 98percent.
92%	With sodium nitrite; In sulfuric acid;	Example 20 Sodium nitrite (2.07 g) was dissolved in a 70 wt. percent aqueous sulfuric acid solution (100 ml), and <strong>[3441-01-8]m-cyanobenzamide</strong> (2.92 g) was added to the resultant solution. The mixture was allowed to react at 40° C. for one hour with stirring. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 2.68 g of m-cyanobenzoic acid (yield 92percent). The m-cyanobenzoic acid obtained had a purity of 99percent or more.
92%		The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 2.68 g of m-cyanobenzoic acid (yield 92percent, based on <strong>[3441-01-8]m-cyanobenzamide</strong>). The m-cyanobenzoic acid obtained had a purity of 99percent or more.

92%	With nitrosylsulfuric acid; In sulfuric acid;	Example 27 A 70 wt. percent aqueous solution (100 ml) of sulfuric acid and <strong>[3441-01-8]m-cyanobenzamide</strong> (2.92 g) were placed in a 200-ml three-neck flask, and the resultant mixture was stirred. Subsequently, a 50 wt. percent solution (10 g) of nitrosylsulfuric acid, obtained through dissolution of nitrosylsulfuric acid (5 g) in sulfuric acid (5 g), was added dropwise to the mixture. When the addition was completed, the mixture was allowed to react at room temperature for 30 minutes. The precipitated crystals were collected, washed with water, and dried, to thereby obtain 2.68 g of m-cyanobenzoic acid (yield 92percent). The m-cyanobenzoic acid obtained had a purity of 98percent or more.
88%	With methanesulfonic acid; dimethyl sulfoxide; sodium nitrite; In water;	Example 23 m-Cyanobenzamide (2.92 g), sodium nitrite (2.76 g), and dimethyl sulfoxide (50 ml) were mixed and stirred vigorously at room temperature. To the mixture, methanesulfonic acid (3.95 g) was added dropwise over ten minutes, and further stirred vigorously for three hours. The solvent was removed under reduced pressure, and water (50 ml) was added to the residue. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 2.57 g of m-cyanobenzoic acid (yield 88percent). The obtained m-cyanobenzoic acid had a purity of 96percent.

Reference： [1]Patent: US6433211,2002,B1
[2]Patent: US6433211,2002,B1
[3]Patent: US6433211,2002,B1
[4]Patent: US6433211,2002,B1
[5]Patent: US6433211,2002,B1

12
[ 46133-07-7 ]
[ 626-17-5 ]
[ 3441-01-8 ]

Reference： [1]Synthesis,2011,p. 2639 - 2643

13
[ 3441-01-8 ]
[ 78950-37-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Lawessons reagent; In tetrahydrofuran; at 23℃; for 1h;	General procedure: Amides (1 mmol) and Lawesson's reagent (490 mg, 1.2 mmol) were added to dry THF (15 mL). The reaction mixture was stirred at room temperature for 1 h, or heated under reflux for 5 h in the case of the 4-nitro derivative. The solvent was evaporated under reduced pressure and the residue was partitioned between aq NaHCO3 (25 mL) and ethyl acetate (25 mL). The organic solvent was separated and dried over anhydrous MgSO4. The crude product was further purified by silica gel flash chromatography, using hexane-ethyl acetate (4:1), to yield the corresponding thioamides as yellow solids (42-60percent). 4-Nitrothioamide (2ff),38 4-cyanothiobenzamide (2gg)39 and 3-cyanothiobenzamide (2hh),40 3-methoxythiobenzamide (2ii)41 have been previously reported.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 510 - 520

14
[ 3441-01-8 ]
[ 1740-57-4 ]

Reference： [1]Catalysis science and technology,2015,vol. 5,p. 2865 - 2868

15
[ 3441-01-8 ]
3-cyano-N-[10,11-dichloro-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.0²'⁶]dodeca-1⁽⁸⁾,6,9,11-tetraen-3-yl]benzamide [ No CAS ]

Reference： [1]Patent: WO2015/177367,2015,A1

16
[ 3441-01-8 ]
[ 13081-18-0 ]
C₁₃H₉F₃N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 100 3-cyano-A-[10,ll-dichloro-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02'6]dodeca- l(8),6,9,ll-tetraen-3-yl]benzamide (ABR 239453) To a stirred solution of <strong>[3441-01-8]3-cyanobenzamide</strong> (650 mg, 4.45 mmol) in DMF (7 mL) was added pyridine (378 mu, 4.45 mmol) followed by ethyl 3,3,3-trifluoro-2-oxopropanoate (590 mu, 4.45 mmol) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h. Thionyl chloride (323 mu, 4.45 mmol) was added at 0°C. The reaction mixture was then stirred at room temperature for a further 16 h and before the reaction mixture was concentrated. The acyl intermediate that remained was dissolved in DMF (5 mL) under argon. 5,6-Dichloro- lH-l,3-benzodiazol-2-amine (674 mg, 3.34 mmol) and triethylamine (934 mu, 6.67 mmol) were added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SC>4), filtered and concentrated. The crude product was purified by silica chromatography, using 3percent MeOH in DCM as eluent. Further purification was carried out by trituration in DCM/MeOH and then pentane to afford the title compound as a white solid (25 mg, 1percent).

Reference： [1]Patent: WO2015/177367,2015,A1 .Location in patent: Page/Page column 130; 131

17
[ 3441-01-8 ]
tert-butyl 4-(10-bromo-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate [ No CAS ]
tert-butyl 4-{10-[(3-cyanobenzoyl)amino]-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl}piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium phosphate; t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2?,4?,6?-triisopropyl-1,1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate; at 110℃; for 16h;Inert atmosphere;	Under argon, tert-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (200 mg, 447 muiotaetaomicron), <strong>[3441-01-8]3-cyanobenzamide</strong> (163 mg, 1.12 mmol), Tripotassium phosphate (133 mg, 626 muiotaetaomicron), tBuBrettPhos (13.0 mg, 26.8 muiotaetaomicron), and tBuBrettPhos Pd G3 (22.9 mg, 26.8 muiotaetaomicron) were dissolved in l-Methoxy-2-propanol (5.0 ml, 52 mmol). The mixture was stirred at 110 °C for 16 h and then purified via reverse phase chromatography (Method: Reprosil C18; 10 muiotaeta; 125x30 mm / flow: 50 ml/min / solvents: A = water (0,01percent formic acid), B = Acetonitrile / gradient 0.00-4.25 min = 20percentB, 4.50min = 30percentB, 19.00-22.50min = 100percentB, 22.75-25.00min = 20percentB) which afforded the product after drying in vacuo. The obtained amout was 130 mg (100 percent purity, 57 percent of theory). LC-MS (Method 1): Rt = 1.15 min; MS (ESIpos): m/z = 513 [M+H]+

Reference： [1]Patent: WO2016/173948,2016,A1 .Location in patent: Page/Page column 166

18
[ 3441-01-8 ]
tert-butyl 4-(10-bromo-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate [ No CAS ]
3-cyano-N-[2-oxo-4-(piperidin-4-yl)-1,2-dihydropyrimido[1,2-b]indazol-10-yl]benzamide hydrochloride [ No CAS ]

Reference： [1]Patent: WO2016/173948,2016,A1

19
[ 3441-01-8 ]
[ 123-54-6 ]
3-cyano-N-((Z)-1-methyl-3-oxobut-1-enyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With toluene-4-sulfonic acid; In toluene; for 5.5h;Reflux;	General procedure: p-Toluenesulfonic acid (4e20 molpercent) was added to a stirred solutionof amide (1.0 equiv) and diketone (0.8e6.3 equiv) in solventand the mixture was stirred for a period of time at reflux temperature.After that the mixture was allowed to cool to room temperature.The mixturewas washed with saturated aqueous NaHCO3and water, dried over Na2SO4 and solvent was evaporated in vacuo.The residue was purified by silica gel column chromatography orrecrystallization to afford pure substituted enamides

Reference： [1]Tetrahedron,2017,vol. 73,p. 1247 - 1254

20
[ 3441-01-8 ]
[ 123-54-6 ]
3-(5-acetyl-4-methyloxazol-2-yl)benzonitrile [ No CAS ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 1247 - 1254

21
[ 626-17-5 ]
[ 3441-01-8 ]
[ 1740-57-4 ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 1870 - 1875

22
[ 3441-01-8 ]
methyl 1-(4-bromophenyl)-3-hydroxycyclobutanecarboxylate [ No CAS ]
methyl 1-(4-(3-cyanobenzamido)phenyl)-3-hydroxycyclobutane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In 1,4-dioxane; at 120℃; for 17h;Inert atmosphere;	To a vial were added methyl l-(4-bromophenyl)-3- hydroxycyclobutanecarboxylate (335.8 mg, 1.178 mmol), <strong>[3441-01-8]3-cyanobenzamide</strong> (258 mg, 1.77 mmol), copper(I) iodide (40.4 mg, 0.212 mmol), (lS,2S)-Nl,N2-dimethylcyclohexane-l,2- diamine (80 mg, 0.56 mmol), K2CO3 (331 mg, 2.39 mmol) and dioxane (6 mL). The mixture was evacuated and backfilled with N2 for 4 times, then heated at 120 °C for 17 h. The mixture was diluted with water and EtOAc. After extraction, the combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by column chromatography on silica gel (EtOAc in hexane : 0-100percent gradient) to afford the title compound. MS (EI) m/z 373 [M+Na]+.

Reference： [1]Patent: WO2019/27855,2019,A1 .Location in patent: Page/Page column 58

23
[ 3441-01-8 ]
2-(3-(4-bromophenyl)oxetan-3-yl)-6-chloro-1H-benzo[d]imidazole [ No CAS ]
[ 76-05-1 ]
N-(4-(3-(6-chloro-1H-benzo[d]imidazol-2-yl)oxetan-3-yl)phenyl)-3-cyanobenzamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a vial were added 2-(3-(4-bromophenyl)oxetan-3-yl)-6-chloro-lH- benzo[d]imidazole (50 mg, 0.14 mmol), <strong>[3441-01-8]3-cyanobenzamide</strong> (24.1 mg, 0.165 mmol), (1 S,2S)- N,N'-dimethylcyclohexane-l,2-diamine (7.8 mg, 0.055 mmol), copper(I) iodide (5.2 mg, 0.028 mmol), K2CO3 (44 mg, 0.32 mmol) and dioxane (700 mu). The mixture was evacuated and backfilled with N2 for 4 times, then heated at 120 °C for 17 h. The mixture was filtered and purified by reversed phase HPLC, eluting with water (0.1percentTFA)-ACN to afford the title compound as a TFA salt (Ex. 11). XH NMR (499 MHz, DMSO-c) delta 10.50 (s, 1H), 8.40 (s, 1H), 8.24 (d, J= 7.1 Hz, 1H), 8.07 (d, J = 6.8 Hz, 1H), 7.88 - 7.70 (m, 3H), 7.71 - 7.50 (m, 2H), 7.38 (d, J= 7.5 Hz, 2H), 7.27 (d, J = 7.9 Hz, 1H), 5.36 (d, J= 4.9 Hz, 2H), 5.15 (d, J = 5.0 Hz, 2H); MS (EI) m/z 429 [M+H]+.

Reference： [1]Patent: WO2019/27855,2019,A1 .Location in patent: Page/Page column 42-43

24
[ 3441-01-8 ]
1-(4-(3-cyanobenzamido)phenyl)-3-hydroxycyclobutane-1-carboxylic acid [ No CAS ]