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[ CAS No. 4943-86-6 ] {[proInfo.proName]}

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Chemical Structure| 4943-86-6
Chemical Structure| 4943-86-6
Structure of 4943-86-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4943-86-6 ]

CAS No. :4943-86-6 MDL No. :MFCD00170586
Formula : C13H11ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :RHCJFZKQYODIDI-UHFFFAOYSA-N
M.W : 246.69 Pubchem ID :670472
Synonyms :

Calculated chemistry of [ 4943-86-6 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 70.07
TPSA : 55.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 4.17
Log Po/w (WLOGP) : 2.99
Log Po/w (MLOGP) : 2.93
Log Po/w (SILICOS-IT) : 2.5
Consensus Log Po/w : 2.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.32
Solubility : 0.0118 mg/ml ; 0.0000478 mol/l
Class : Moderately soluble
Log S (Ali) : -5.04
Solubility : 0.00227 mg/ml ; 0.00000921 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.18
Solubility : 0.00164 mg/ml ; 0.00000664 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.46

Safety of [ 4943-86-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P337+P313-P264-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4943-86-6 ]

* 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 [ 4943-86-6 ]

[ 4943-86-6 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 118-48-9 ]
  • [ 106-47-8 ]
  • [ 4943-86-6 ]
YieldReaction ConditionsOperation in experiment
65% at 120℃; for 2h; A mixture of 20 g (123 mmol) isatoic anhydride (formed by treating anthranilic acid with phosgene) and 15.64 g (123 mmol) 4-chloroaniline was heated at 1200C for 2 hours. The reaction was cooled to room temperature, mixed with CH2CI2 and filtered.The filtrate was purified by silica gel chromatography using 30% hexanes in CHCI3 to recover 18.38 g (65%) of a white solid. This was recrystallized from EtOAc to give 11.16 g of a white solid.1NMR
28% In N,N-dimethyl-formamide; at 115℃; for 14h; Example 10. Preparation of 3-(4-chlorophenyl)-2-(4-(2-hydroxyethoxy)-3,5- dimethylphenyl)quinazolin-4(3H)-one; [0169] To a solution of 4-chloroaniline (3.13 g, 24.5 mmol) in N, N- dimethylformide (20 ml_) was added isatoic anhydride (4.00 g, 24.5 mmol), and the reaction mixture was heated at 115C for 14 h, cooled to room temperature and diluted with ethyl acetate (100 ml_). The organic layer was washed with 1 N NaOH (200 mL), water (100 ml_), then brine, and dried over Na2SO4. The solvent was removed under reduced pressure to give crude product, which was purified by column chromatography (silica gel 230-400 mesh; EtOAc/hexane = 1 :9) to give 2- amino-Lambda/-(4-chloro-phenyl)-benzamide as white solid. Yield: 1.67 g (28%).[0170] To a mixture of 4-(2-hydroxyethoxy)-3,5-dimethyl-benzaldehyde (0.420 g, 2.17 mmol) and 2-amino-/V-(4-chloro-phenyl)-benzamide (0.500 g, 2.17 mmol) in Lambda/,Lambda/-dimethylacetamide (5 mL) was added sodium hydrogensulfite (0.350 g, 3.26 mmol) and p-toluenesulfonic acid (0.21 g, 0.11 mmol). The reaction mixture was heated at 155C for 14 hours, cooled to room temperature, and diluted with cold water (20 mL), to produce the precipitate. The yellow solid was filtered, washed with cold water, then methanol, and dried under vacuum to provide crude product, which was purified by preparative HPLC (0.1 % TFA in CH3CN / H2O as eluent) to give the title compound as a white solid. Yield: 0.23 g (14%). MP 101- 1030C. 1H-NMR (400 MHz, CDCI3): delta 8.38 (d, 1 H), 7.81-7.78 (m, 2H), 7.59-7.51 (m, 1 H), 7.31-7.20 (m, 2H), 7.15-7.12 (m, 2H), 7.01-6.98 (d, 2H), 3.98-3.80 (m, 4H), 2.20 (S, 6H), 2.01 (t, 1 H). MS (ES+) m/z: 421.05 (M+1).
With iodine; potassium carbonate; In water; for 3h;Reflux; Green chemistry; General procedure: A mixture of 4-methoxybenzyl alcohol (0.138 g, 1 mmol), I2 (0.254 g, 1 mmol), K2CO3(0.138 g, 1 mmol), isatoic anhydride (0.163 g, 1 mmol) and aniline (0.093 g,1 mmol) in water (5 mL) was stirred for 3 h at reflux. After reaction completion,the mixture was cooled to room temperature and stirred for 1 h. The resultingprecipitate was filtered, washed with water (3 3 mL), and purified by recrystallization from ethanol to give 4a as a white solid.
In ethanol; at 70℃; for 1h; General procedure: To a solution of isatoic anhydride 4 (1 mmol, 163 mg) in 4 ml EtOH was added primary amine or aryl hydrazine or aryl hydrazide 5a-h (1 mmol) and the mixture was heated for 1 hours at 70 C. The mixture was used for the synthesis of 7a-n or 8a-c without purification.

  • 2
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  • [ 20887-03-0 ]
  • 6
  • [ 4943-86-6 ]
  • [ 1710-98-1 ]
  • 2-[(4-tert-Butylbenzoyl)amino]-N-(4-chlorophenyl)benzamide [ No CAS ]
  • 7
  • [ 872-85-5 ]
  • [ 4943-86-6 ]
  • VEGF Receptor Tyrosine Kinase Inhibitor II [ No CAS ]
  • 8
  • [ 4943-86-6 ]
  • [ 73713-79-8 ]
  • N-(4-Chlorophenyl)-2-(2,1,3-benzothiadiazole-4-sulfonylamino)-benzamide [ No CAS ]
  • 11
  • [ 4943-86-6 ]
  • 3-(4-chloro-phenyl)-2,2-dimethyl-2,3-dihydro-1<i>H</i>-quinazoline-4-thione [ No CAS ]
  • 12
  • [ 4943-86-6 ]
  • 4-(4-chloro-phenyl)-1,2-dihydro-benzo[<i>e</i>][1,4]diazepine-3,5-dione [ No CAS ]
  • 14
  • [ 4943-86-6 ]
  • [ 127662-23-1 ]
  • 19
  • [ 4943-86-6 ]
  • 3-(4-Chloro-phenyl)-1-(3,4-dimethoxy-benzyl)-2-methyl-4-oxo-3,4-dihydro-quinazolin-1-ium; perchlorate [ No CAS ]
  • 20
  • [ 4943-86-6 ]
  • 1-(2',4'-dimethoxybenzyl)-2-methyl-3-(4'-chlorophenyl)-4(3H)-quinazolinonium perchlorate [ No CAS ]
  • 22
  • [ 4943-86-6 ]
  • 2-{4-(N,N-dimethylamino)-2-[1-(tert-butoxycarbonyl)piperidin-4-yloxy]benzoylamino}-N-(4-chlorophenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% The 2-( 1 -tert-butoxycarbonylpiperidin-4-yloxy)-4-(N,N-dimethylamino)benzoic acid (950 mg, 2.61 mmol) was dissolved in methylene chloride (15 mL). Pyridine (0.27 mL, 3.39 mmol) and DMF (1 drop) were added, followed by oxalyl chloride (0.27 mL, 3.13 mmol). Vigorous bubbling occurred. After 45 minutes, more pyridine (0.27 mL, 3.39 mmol) was added, followed by the N-(4-chlorophenyl)-2-amino- benzamide (645 mg, 2.61 mmol). The reaction was stirred for 2 hours and then diluted with methylene chloride and washed with 50% saturated aqueous sodium bicarbonate. The organic layer was concentrated and purified by flash column chromatography (about 120 g silica, 100% CH2CI2 to 10% EtOAc/CH2Cl2) to give the desired product (207 mg, 0.35 mmol, 13%). EPO <DP n="42"/>1NMR (300 MHz, CDCl3): delta 8.48 (br s, IH), 8.27 (d, J = 8.4 Hz, IH), 8.07 (d, J = 9.0Hz, IH), 7.57 (m, 4H), 7.42 (m, IH), 7.33 (m, 2H), 7.11 (m, IH), 6.56 (m, 2H), 4.66 (m,IH), 3.75 (m, IH), 3.20 (m, IH), 3.05 (m, 6H), 2.1 (m, 2H), 1.60 (m, 4H), 1.43 (s, 9H).IS-MS, m/e: 593(m+l).
YieldReaction ConditionsOperation in experiment
(2b) 2-Amino-N-[3-fluoro-4-(trifluoromethyl)phenyl]benzamide, m.p. 135-137 C., utilising intermediate 1b. (2c) 2-Amino-N-(4-chlorophenyl)benzamide, m.p. of the hydrochloride salt 156-173 C., utilising intermediate 1c.
  • 24
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  • [ 106-47-8 ]
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  • 25
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  • [ 100-52-7 ]
  • [ 63384-39-4 ]
YieldReaction ConditionsOperation in experiment
With iodine; potassium carbonate; In water; for 3h;Reflux; Green chemistry; General procedure: A mixture of 4-methoxybenzyl alcohol (0.138 g, 1 mmol), I2 (0.254 g, 1 mmol), K2CO3(0.138 g, 1 mmol), isatoic anhydride (0.163 g, 1 mmol) and aniline (0.093 g,1 mmol) in water (5 mL) was stirred for 3 h at reflux. After reaction completion,the mixture was cooled to room temperature and stirred for 1 h. The resultingprecipitate was filtered, washed with water (3 3 mL), and purified by recrystallization from ethanol to give 4a as a white solid.
  • 26
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  • [ 1158178-11-0 ]
  • 27
  • [ 13669-42-6 ]
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  • [ 1235480-14-4 ]
YieldReaction ConditionsOperation in experiment
14% In ethanol; for 4h;Reflux; Example 36. Preparation of 3-(4-chlorophenyl)-2-(quinolin-3-yl)quinazolin-4(3H)-one; [0223] 3-Quinoline carboxaldehyde (0.41 mmol) and anhydrous CuCI2 (0.110 g, 0.82 mmol) were added to a solution of 2-amino-Lambda/-(4- chlorophenyl)benzamide (0.100 g, 0.41 mmol) in anhydrous EtOH (10 ml_). The mixture was heated at reflux temperature for 4 hours and concentrated in vacuo. The residue was dissolved in EtOAc and washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography on silica gel, eluting with 5% to 50% EtOAc in heptane, afforded the title compound as a white solid (14%). 1H-NMR (300 MHz, DMSO-d6): delta 8.83 (d, J = 2.1 Hz, 1 H), 8.45 (d, J = 1.8 Hz, 1 H), 8.24 (d, J = 8.0 Hz, 1 H), 7.88-8.03 (m, 3H), 7.74-7.88 (m, 2H), 7.56-7.73 (m, 2H), 7.52 (d, J = 8.6 Hz, 2H), 7.40 (d, J = 8.7 Hz, 2H). MS (APCI) m/z: 384 (M+H)+.
  • 28
  • [ 23100-12-1 ]
  • [ 4943-86-6 ]
  • [ 1235480-16-6 ]
YieldReaction ConditionsOperation in experiment
4% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 150℃; for 21h; Example 38. Preparation of 3-(4-chlorophenyl)-2-(6-chloropyridin-3-yl)quinazolin- 4(3H)-one; [0225] 2-Amino-Lambda/-(4-chlorophenyl)benzamide (0.500 g, 2.03 mmol) and 6- chloronicotinaldehyde (2.23 mmol), NaHSO3 (0.253 g, 2.44 mmol) and p-TsOH (0.039 g, 0.20 mmol) were dissolved in DMA (20 ml_) and heated at 1500C for 21 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with water (2 x 200 mL), dried (Na2SO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 70% ethyl acetate/heptane, afforded the title compound as a white solid (4%). 1H-NMR (300 MHz, DMSO-d6): delta 8.46 (d, J = 2.1 Hz, 1 H), 8.23 (d, J = 8.1 Hz, 1 H), 7.92-7.97 (m, 1 H), 7.80-7.86 (m, 2H), 7.63-7.68 (m, 1 H), 7.47-7.50 (m, 5H). MS (APCI) m/z: 368 (M+H)+.
  • 29
  • [ 18515-67-8 ]
  • [ 4943-86-6 ]
  • [ 1235480-98-4 ]
YieldReaction ConditionsOperation in experiment
48% With copper dichloride; In ethanol; for 3.5h;Reflux; Example 73. Preparation of 3-(4-chlorophenyl)-2-(1 H-indol-5-yl)quinazolin-4(3H)- one; [0265] <strong>[18515-67-8]3-methyl-4-nitro-benzaldehyde</strong> (0.268 g, 1.60 mmol) and anyhydrous CuCb (0.437 g, 3.20 mmol) were added to a solution of 2-amino-Lambda/-(4- chlorophenyl)benzamide (0.400 g, 1.60 mmol) in anyhydrous EtOH (15 ml_) and heated at reflux temperature for 3.5 hours. After concentration in vacuo and dissolving the residue in EtOAc, the organics were washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 70% EtOAc in heptane, afforded 3-(4-chlorophenyl)-2-(3-methyl-4-nitrophenyl)quinazolin-4(3H)-one (0.300 g, 48%).[0266] te/t-butoxybis(dimethylamino)methane (0.47 ml_, 2.30 mmol) was added to a solution of 3-(4-chlorophenyl)-2-(3-methyl-4-nitrophenyl)quinazolin-4(3/-/)- one (0.300 g, 0.76 mmol) in DMF (30 ml_). After heating at 400C for 3.5 hours, concentration in vacuo afforded (£)-3-(4-Chlorophenyl)-2-(3-(2- (dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3H)-one (0.342 g, 100%).[0267] Zn dust (0.220 g, 3.35 mmol) was added to a solution of (E)-3-(4- chlorophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3/-/)-one in AcOH (15 ml_). After heating and stirring at reflux temperature for 4 hours, the mixture was basified with 1 N NaOH and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 20% to 90% EtOAc in heptane, afford the title compound as a white solid (0.048 g, 39%). 1H-NMR (300 MHz, DMSO-de): delta 11.19 (s, 1 H), 8.18-8.21 (m, 1 H), 7.88-8.00 (m, 1 H), 7.75 (d, J = 7.7 Hz, 1 H), 7.47-7.70 (m, 2H), 7.30-7.44 (m, 5H), 7.20 (d, J = 8.4 Hz, 1 H), 7.06 (d, J = 6.8 Hz, 1 H), 6.40 (d, J = 2.0 Hz, 1 H). MS (APCI) m/z: 372 (M+H)+.
  • 30
  • [ 15174-69-3 ]
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  • [ 1235480-90-6 ]
YieldReaction ConditionsOperation in experiment
57% With copper dichloride; In ethanol; for 4h;Reflux; Example 34. Preparation of 3-(4-chlorophenyl)-2-(4-(2-hydroxyethoxy)-3- methylphenyl)quinazolin-4(3H)-one; [0219] Anhydrous CuCI2 (0.306 g, 2.20 mmol) and 4-hydroxy-3- methylbenzaldehyde (0.155 g, 1.10 mmol) were added to a solution of 2-amino-Lambda/-(4- chlorophenyl)benzamide (0.280 g, 1.10 mmol) in anhydrous EtOH (10 ml_). The mixture was heated at reflux temperature for 4 hours and concentrated in vacuo. The residue was dissolved in EtOAc, washed with H2O and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% to 50% EtOAc in heptane, afforded 3-(4-chlorophenyl)-2-(4- hydroxy-3-methylphenyl)quinazolin-4(3H)-one (0.230 g, 57%).[0220] K2CO3 (0.131 g, 0.95 mmol) was added to a solution of 3-(4- chlorophenyl)-2-(4-hydroxy-3-methylphenyl)quinazolin-4(3H)-one (0.230 g, 0.63 mmol) in DMF (15 ml_) and stirred for 30 min. (2-Bromoethoxy)(tert- butyl)dimethylsilane (0.16 ml_, 0.76 mmol) was added and the reaction was heated to reflux temperature for 3 hours, and concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3, and then brine, dried (Na2SO4), filtered, and concentrated in vacuo, to afford 2-(4-(2-(feAt-Butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4-chlorophenyl)quinazolin-4(3/-/)- one (0.340 g, quantitative).[0221] A 1 M THF solution of TBAF (1.90 ml_, 1.90 mmol) was added to a solution of 2-(4-(2-(te/t-butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4- chlorophenyl)quinazolin-4(3H)-one (0.340 g, 0.65 mmol) in THF (5 ml_). The mixture was stirred at room temperature for 1 hour and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 100% EtOAc in heptane, afforded the title compound as a white solid (0.190 g, 72%). 1H-NMR (300 MHz, DMSO-de): delta 8.17 (dd, J = 6.8, 1.0 Hz, 1 H), 7.89 (d, J = 6.8 Hz, 1 H), 7.75 (d, J = 8.8 Hz, 1 H), 7.55-7.59 (m, 1 H), 7.28-7.48 (m, 4H), 7.21 (d, J = 1.5 Hz, 1 H), 7.04-7.16 (m, 1 H), 6.77 (d, J = 8.7 Hz, 1 H), 4.81 (t, J = 5.7 Hz, 1 H), 3.86-4.01 (m, 2H), 3.60-3.77 (m, 2H), 2.06 (s, 3H). MS (APCI) m/z: 407 (M+H)+.
  • 31
  • [ 31680-07-6 ]
  • [ 4943-86-6 ]
  • [ 1235481-15-8 ]
YieldReaction ConditionsOperation in experiment
63% With copper dichloride; In ethanol; for 3h;Reflux; Example 85. Preparation of 3-(4-chlorophenyl)-2-(1 H-indol-6-yl)quinazolin-4(3H)- one; [0295] <strong>[31680-07-6]4-methyl-3-nitrobenzaldehyde</strong> (0.270 g, 1.60 mmol) and anhydrous CuCI2 (0.435 g, 3.20 mmol) were added to a solution of 2-amino-Lambda/-(4- chlorophenyl)benzamide (0.400 g, 1.60 mmol) in anhydrous EtOH (10 mL). After heating at reflux temperature for 3 hours, the reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% to 60% EtOAc in heptane, afforded 3-(4-chlorophenyl)- 2-(4-methyl-3-nitrophenyl)quinazolin-4(3H)-one (0.400 g, 63%).[0296] teAf-butoxybis(dimethylamino)methane (0.50 mL, 2.30 mmol) was added to a solution of 3-(4-chlorophenyl)-2-(4-methyl-3-nitrophenyl)quinazolin-4(3/-/)- one (0.300 g, 0.76 mmol) in DMF (20 mL). Stirring at 500C for 3 hours and concentrating in vacuo afforded (£)-3-(4-chlorophenyl)-2-(4-(2-(dimethylamino)vinyl)- 3-nitrophenyl)quinazolin-4(3H)-one (0.340 g, 100%).[0297] A solution of (E)-3-(4-chlorophenyl)-2-(4-(2-(dimethylamino)vinyl)-3- nitrophenyl)quinazolin-4(3/-y)-one (0.340 g, 0.76 mmol) in a 3:1 mixture of EtOH/DMF (50 mL) was flushed with N2. Pd/C (0.034 g, 10 wt%) was added the reaction was flushed with H2 for 1.5 hours. After filtering through diatomaceous earth, the filtrate was concentrated. Purification by flash chromatography on silica gel, eluting with 5% to 70% EtOAc in heptane, afforded the title compound as a white solid (0.105 g, 37%). 1H-NMR (300 MHz, DMSO-d6, mixture of rotamers): delta 11.34 (s, 0.5H), 11.25 (s, 0.5 H), 8.16-8.29 (m, 1 H), 7.86-8.00 (m, 1H), 7.71-7.82 (m, 1 H), 7.49-7.67 (m, 3H), 7.29-7.48 (m, 5H), 6.87-7.05 (m, 1 H), 6.37-6.42 (m, 0.5H), 6.25-6.26 (m, 0.5H). MS (APCI) m/z: 372 (M+H)+.
  • 32
  • [ 1039948-89-4 ]
  • [ 4943-86-6 ]
  • [ 1235479-88-5 ]
YieldReaction ConditionsOperation in experiment
14% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 155℃; for 14.0h; Example 10. Preparation of 3-(4-chlorophenyl)-2-(4-(2-hydroxyethoxy)-3,5- dimethylphenyl)quinazolin-4(3H)-one; [0169] To a solution of 4-chloroaniline (3.13 g, 24.5 mmol) in N, N- dimethylformide (20 ml_) was added isatoic anhydride (4.00 g, 24.5 mmol), and the reaction mixture was heated at 115C for 14 h, cooled to room temperature and diluted with ethyl acetate (100 ml_). The organic layer was washed with 1 N NaOH (200 mL), water (100 ml_), then brine, and dried over Na2SO4. The solvent was removed under reduced pressure to give crude product, which was purified by column chromatography (silica gel 230-400 mesh; EtOAc/hexane = 1 :9) to give 2- amino-Lambda/-(4-chloro-phenyl)-benzamide as white solid. Yield: 1.67 g (28%).[0170] To a mixture of 4-(2-hydroxyethoxy)-3,5-dimethyl-benzaldehyde (0.420 g, 2.17 mmol) and 2-amino-/V-(4-chloro-phenyl)-benzamide (0.500 g, 2.17 mmol) in Lambda/,Lambda/-dimethylacetamide (5 mL) was added sodium hydrogensulfite (0.350 g, 3.26 mmol) and p-toluenesulfonic acid (0.21 g, 0.11 mmol). The reaction mixture was heated at 155C for 14 hours, cooled to room temperature, and diluted with cold water (20 mL), to produce the precipitate. The yellow solid was filtered, washed with cold water, then methanol, and dried under vacuum to provide crude product, which was purified by preparative HPLC (0.1 % TFA in CH3CN / H2O as eluent) to give the title compound as a white solid. Yield: 0.23 g (14%). MP 101- 1030C. 1H-NMR (400 MHz, CDCI3): delta 8.38 (d, 1 H), 7.81-7.78 (m, 2H), 7.59-7.51 (m, 1 H), 7.31-7.20 (m, 2H), 7.15-7.12 (m, 2H), 7.01-6.98 (d, 2H), 3.98-3.80 (m, 4H), 2.20 (S, 6H), 2.01 (t, 1 H). MS (ES+) m/z: 421.05 (M+1).
  • 33
  • [ 241816-11-5 ]
  • [ 4943-86-6 ]
  • [ 1235480-26-8 ]
YieldReaction ConditionsOperation in experiment
35% With copper dichloride; In ethanol; for 5h;Reflux; Example 48. Preparation of 3-(4-chlorophenyl)-2-(6-(piperidin-1-yl)pyridin-3- yl)quinazolin-4(3H)-one; [0235] 2-amino-Lambda/-(4-chlorophenyl)benzamide (0.318 g, 1.3 mmol) and 6- (piperidin-i-yl)nicotinaldehyde (1.3 mmol) were mixed in anhydrous EtOH (40 ml_) and anhydrous CuCI2 (0.524 g, 3.9 mmol) was added. The reaction mixture was heated at reflux for 5 hours, cooled to room temperature, and stirred overnight. The reaction mixture was concentrated, diluted with ethyl acetate (150 ml_), washed with water (2 * 100 m._), dried (MgSO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 75% ethyl acetate/heptane, afforded the title compound as a white solid (35%). 1H-NMR (300 MHz, DMSO-d6): delta 8.16 (d, J = 8.0 Hz, 1 H), 8.11 (d, J = 2.4 Hz, 1 H), 7.86-7.91 (m, 1H), 7.74 (d, J = 8.0 Hz, 1 H), 7.54-7.59 (m, 1 H), 7.36-7.50 (m, 5H), 6.64 (d, J = 9.0 Hz, 1 H), 3.49-3.53 (m, 4H), 1.48-1.58 (m, 6H). MS (APCI) m/z: 417 (M+H)+.
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  • [ 1323401-52-0 ]
  • 46
  • [ 4943-86-6 ]
  • [ 2393-23-9 ]
  • [ 1374321-48-8 ]
  • 47
  • [ 4943-86-6 ]
  • [ 140-75-0 ]
  • [ 1374321-44-4 ]
  • 48
  • [ 4943-86-6 ]
  • [ 100-46-9 ]
  • [ 1374321-41-1 ]
  • 49
  • [ 4943-86-6 ]
  • [ 104-84-7 ]
  • [ 1262424-48-5 ]
  • 50
  • [ 13679-70-4 ]
  • [ 4943-86-6 ]
  • C19H15ClN2OS [ No CAS ]
  • 51
  • [ 13679-70-4 ]
  • [ 4943-86-6 ]
  • [ 385777-37-7 ]
  • 52
  • [ 4943-86-6 ]
  • [ 6630-33-7 ]
  • 2-(2-bromophenyl)-3-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile; at 20℃; General procedure: A solution of the substituted benzamide (1equiv) and ortho-bromobenzaldehyde(1.41 mmol, 1 equiv) in acetonitrile (5mL) was treated with cyanuric chloride(0.022 mmol, 10 mole %). The reaction mixture was stirred at room temperature for 5-10 min and formed precipitate was filtered and recrystallised with ethanol to obtain the compounds 1, 6a, 6b and 16.
  • 53
  • [ 4943-86-6 ]
  • 3-(4-chlorophenyl)-2-isopropyl-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
  • 54
  • [ 4943-86-6 ]
  • 3-(4-chlorophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
  • 55
  • [ 4943-86-6 ]
  • 3-(4-chlorophenyl)-2-isobutyl-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
  • 56
  • [ 127-19-5 ]
  • [ 4943-86-6 ]
  • [ 24122-31-4 ]
  • 57
  • [ 119072-55-8 ]
  • [ 4943-86-6 ]
  • 2-(tert-butylamino)-3-(4-chlorophenyl)quinazolin-4(3H)-one [ No CAS ]
  • 58
  • 4-(4-methyl-1,4-diazepan-1-yl)benzoyl chloride hydrochloride [ No CAS ]
  • [ 4943-86-6 ]
  • C26H27ClN4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
423 mg With pyridine; for 24h; General procedure: 7.1.12 5-Chloro-3-hydroxy-4'-methoxy-2-[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzanilide hydrochloride (19) To a stirred solution of compound 18 (430 mg, 1.47 mmol) in pyridine (10 mL) was added compound 37 (577 mg, 2.00 mmol). After 24 h, the reaction mixture was concentrated in vacuo. The residue was diluted with CHCl3 and washed with 5% aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was subjected to chromatography over silica gel eluting with CHCl3/MeOH (100:5 by volume). The resulting material was dissolved in EtOH (10 mL) and added 1 N hydrochloric acid (0.8 mL), and the whole was stirred for 0.5 h. The resulting precipitate was filtered off and dried to yield the title compound as a colorless solid (250 mg, 31%): mp 248-251 C; 7.1.13. Solution-phase synthesis of library compounds 21Isatoic anhydride (20) (0.1 mmol) was partitioned into reaction vials and treated with aniline (0.10 mmol) in toluene (1.0 mL) at 100 C for 12 h. The mixture in each vessel was allowed to coolto ambient temperature, and the solvent was removed under reduced pressure. The residue in each vessel was dissolved in pyridine(1.0 mL) and treated with compound 37 (0.10 mol) at ambient temperature for 12 h. The mixture was then treated with polymer-bound tris(2-aminoethyl)amine for 12 h and filtered off. The filtrate was collected in vials and the solutions were evaporatedin vacuo to afford anthranilamide derivatives 21, which were analyzed by HPLC and MS. 21a; FAB-MS m/z 443 [M+H]+, 21b; FABMS m/z 443 [M+H]+, 21c; FAB-MS m/z 443 [M+H]+, 21d; FAB-MS m/z 463 [M+H]+, 21e; FAB-MS m/z 463 [M+H]+, 21g; FAB-MS m/z459 [M+H]+, 21h; FAB-MS m/z 489 [M+H]+, 21i; FAB-MS m/z 493[M+H]+, 21j; FAB-MS m/z 513 [M+H]+, 21k; FAB-MS m/z 521[M+H]+, 21l; FAB-MS m/z 472 [M+H]+, 21m; FAB-MS m/z 457 [M+H]+, 21n; FAB-MS m/z 471 [M+H]+, 21o; FAB-MS m/z 430[M+H]+, 21p; FAB-MS m/z 444 [M+H]+, 21q; FAB-MS m/z 444[M+H]+, 21r; FAB-MS m/z 444 [M+H]+, 21s; FAB-MS m/z 460 [M+H]+, 21t; FAB-MS m/z 449 [M]+, 21u; FAB-MS m/z 433[M+H]+, 21v; FAB-MS m/z 469 [M+H]+, 21w; FAB-MS m/z 480[M+H]+. Compound 21f was obtained from 2-amino-5-chloro-3-hydroxy-40-methoxybenzanilide using the methods described forthe synthesis of compound 19 as a colorless solid (423 mg, 56%):
  • 59
  • [ 4943-86-6 ]
  • [ 113247-36-2 ]
  • methyl 1-(3-(4-chlorophenyl)-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate [ No CAS ]
  • 60
  • [ 4943-86-6 ]
  • [ 3535-37-3 ]
  • N-(2-(4-chlorophenylcarbamoyl)phenyl)-3,4-dimethoxybenzamide [ No CAS ]
  • 61
  • [ 329-15-7 ]
  • [ 4943-86-6 ]
  • N-(4-chlorophenyl)-2-(4-(trifluoromethyl)benzamido)benzamide [ No CAS ]
  • 62
  • [ 80-43-3 ]
  • [ 4943-86-6 ]
  • [ 24122-31-4 ]
  • 63
  • [ 4943-86-6 ]
  • [ 123-54-6 ]
  • [ 1788-93-8 ]
YieldReaction ConditionsOperation in experiment
69% With camphor-10-sulfonic acid; In water; at 100℃; for 24h; 2-Amino-N-(p-chlorophenyl) benzamide (49.2 mg, 0.2 mmol), Camphorsulfonic acid (4.6 mg, 10 mol%) And 2,4-pentanedione (30.0 mg, 0.3 mmol) were added to 1 mL of a mixed solvent (Vwater : VLactic acid ethyl ester = 9:1) The reaction was carried out at 100 C for 24 h, and purified by thin layer chromatography to give 37.3 mg of 3-(4-chlorophenyl)-2-methylquinazolinone, yield 69%, purity 98%
62% With iron(III) chloride hexahydrate; In water; at 100℃; for 24h;Green chemistry; General procedure: A flask was charged with 2-aminobenzamide (1a; 27.2 mg, 0.2 mmol), pentane-2,4-dione (2A;30.0 mg, 0.3 mmol), FeCl3·6H2O (10.8 mg, 0.04 mmol), and PEG-400/H2O (1.0 mL, 1:9 (v/v)).The reaction was stirred at 100 C for 24 h. When the reaction was complete monitored by TLC,the mixture was cooled to room temperature, extracted with EtOAc (3×20 mL). The combined organic phase was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the product 3aA (29.3 mg, 91%) as white solid.
  • 64
  • [ 504-02-9 ]
  • [ 4943-86-6 ]
  • 3-(4-chlorophenyl)-2-(4-oxopentyl)quinazolin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With camphor-10-sulfonic acid; In water; ethyl acetate; at 100℃; for 24h; 2-amino-N- (4-chlorophenyl) benzamide (49.2 mg, 0.2 mmol)Camphorsulfonic acid (4.6 mg, 10 mol%) and 1,3-cyclohexanedione (33.6 mg, 0.3 mmol) were added to 1 mL of a mixed solvent (V aqueous: v ethyl lactate = 9: 1)100C under the reaction 24h, thin layer chromatography to obtain3- (4-chlorophenyl) -2- (4-oxopentyl) quinazolinone57.1 mg, yield 84%, purity 98%
  • 65
  • [ 104-88-1 ]
  • [ 4943-86-6 ]
  • 2,3-di-(p-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine; potassium carbonate; In water; for 3h;Reflux; Green chemistry; General procedure: A mixture of 4-methoxybenzyl alcohol (0.138 g, 1 mmol), I2 (0.254 g, 1 mmol), K2CO3(0.138 g, 1 mmol), isatoic anhydride (0.163 g, 1 mmol) and aniline (0.093 g,1 mmol) in water (5 mL) was stirred for 3 h at reflux. After reaction completion,the mixture was cooled to room temperature and stirred for 1 h. The resultingprecipitate was filtered, washed with water (3 3 mL), and purified by recrystallization from ethanol to give 4a as a white solid.
  • 66
  • [ 4943-86-6 ]
  • [ 123-11-5 ]
  • [ 311794-86-2 ]
YieldReaction ConditionsOperation in experiment
With iodine; potassium carbonate; In water; for 3h;Reflux; Green chemistry; General procedure: A mixture of 4-methoxybenzyl alcohol (0.138 g, 1 mmol), I2 (0.254 g, 1 mmol), K2CO3(0.138 g, 1 mmol), isatoic anhydride (0.163 g, 1 mmol) and aniline (0.093 g,1 mmol) in water (5 mL) was stirred for 3 h at reflux. After reaction completion,the mixture was cooled to room temperature and stirred for 1 h. The resultingprecipitate was filtered, washed with water (3 3 mL), and purified by recrystallization from ethanol to give 4a as a white solid.
  • 67
  • [ 4943-86-6 ]
  • [ 72553-60-7 ]
YieldReaction ConditionsOperation in experiment
88% With tert.-butylnitrite; saccharin; In ethanol; at 50℃; for 6h;Green chemistry; General procedure: Initially, 2-amino-N-(arylphenyl)-benzamide (0.484 g, 2.0mmol) (1) was added with slow stirring to a mixture of Sac-H (0.037 g, 0.2mmol) and tert-butyl nitrite (0.40mL, ,3.0mmol) in dry ethanol (5mL) for 5 min at room temperature. Then, stirring was continued for 6 h. The solvent, by-product tert-BuOH, and excess tert-BuONO were evaporated under reduced pressure after completion of the reaction (monitored by TLC). The crude residue was purified by column chromatography on silica gel with light petroleum/ethyl acetate (8 : 2 to 7 : 3 v/v) to give the pure products.
86% With tert.-butylnitrite; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 60℃; for 12h;Sealed tube; General procedure: 2-aminobenzamides (1a-z, 0.2 mmol), TBAI (3.7 mg, 0.01 mol), tert-butylnitrite (72 muL, 0.6 mmol) and CH3CN (2.0 mL) were successively addedto a 10 mL of sealed tube. The mixture was stirred at 60 C for 12 h at air. The solution was then cooled to r.t. and evaporated undervaccum. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 6:1 to 3:1) to afford the desired products3a-z.
86% With tert.-butylnitrite; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 60℃; for 12h;Green chemistry; The reaction flask was added 1l (2mmol, 493mg),and then added tert-butyl nitrite (6mmol, 0.72mL),followed by tetrabutylammonium iodide (5mol%,37 mg of) and acetonitrile (20mL). Then the system was heated for 12 hours at 60 deg C. for air, vacuum spin dry acetateAfter the nitrile with petroleum ether / ethyl acetate = 6/1 mixed solvent of a simple column chromatography to give the product 2L, 86% yield. yellowsolid,
  • 68
  • [ 4943-86-6 ]
  • [ 135518-73-9 ]
  • 3-(4-chlorophenyl)-2-(4-oxo-4H-chromen-3-yl)-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With methanesulfonic acid; In ethanol; at 70℃; for 12h; General procedure: To a solution of product 6a-h (1 mmol) in 10 mL EtOH was added product 3 (1 mmol), and methanesulfonic acid (20 mol%, 20mg) and the mixture was heated for 12h at 70 C. The reaction reached completion as indicated by TLC (ethyl acetate: n-hexane, 1:3) and the precipitate was filtered. The precipitate was washed with methanol. The resulting powder was the pure product 7a-n (Yields 48-84%).
  • 69
  • [ 75-15-0 ]
  • [ 4943-86-6 ]
  • [ 1028-40-6 ]
YieldReaction ConditionsOperation in experiment
34% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20℃; for 15.5h; General procedure: To a solution of 3 (80.6 mg, 260 mumol) and CS2 (300 muL, 5.00 mmol) in DMF (2.0 mL) was added DBU (38.7 muL, 258 mumol). The reaction mixture was stirred for 15.5 h at r.t., and then diluted with AcOEt. The organic layer was washed with 2 N HCl aq, water and brine, then dried and concentrated to afford the title compound (87.7 mg, 0.248 mmol, 96%) as a pale yellow solid (recrystallized from CHCl3/MeOH).
  • 71
  • [ 4943-86-6 ]
  • [ 121-44-8 ]
  • 3-(4-chlorophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(I) oxide; tricyclohexylphosphine; In chloroform; at 100℃; for 24h;Schlenk technique; Sealed tube; General procedure: A reaction tube was charged under air with 2-aminobenzanilide(1a, 0.2 mmol), Et3N (2a, 0.6 mmol), Cu2O (10 mol%), PCy3(10 mol%), and CHCl3 (2 mL). The vessel was sealed, heated at100 C (oil-bath temperature) for 24 h, and then cooled to r.t.DDQ (1 equiv) was added, and the mixture was kept at r.t. for 1h. After filtration of the mixture and evaporation of the solventunder reduced pressure, the crude product was purified by column chromatography [silica gel, hexane-EtOAc (3:1)] to givea light-yellow solid;
  • 72
  • [ 4943-86-6 ]
  • [ 431-03-8 ]
  • 2-acetyl-3-(4-chlorophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With iodine; at 50℃; for 6h;Ionic liquid; Inert atmosphere; Green chemistry; General procedure: A dry 50-mL flask was charged with 2-aminobenzamide 1 (1.0 mmol) and 1,2-dicarbonyl compound 2 (1.0 mmol), iodine (13 mg, 0.05 mmol), and [BMIm]Br (2.0 mL). The reaction mixture was stirred at 50 C under anhydrous atmosphere for 6-10 h. After the completion of the reaction as indicated by TLC [a small amount of reaction mixture was dissolved in EtOH, and the developing solvent is a mixture of ethyl acetate and petroleum ether (volume ratio 3:1)], 5 mL water was added to the mixture. The yellow precipitate was filtered off and purified by recrystallization from 95% EtOH to give final product 3.
  • 73
  • [ 5271-67-0 ]
  • [ 4943-86-6 ]
  • N-(4-chlorophenyl)-2-(thiophen-2-ylcarbonylamino)benzamide [ No CAS ]
  • 74
  • [ 42518-98-9 ]
  • [ 4943-86-6 ]
  • N-(4-chlorophenyl)-2-((5-chlorothiophen-2-yl)carbonylamino)benzamide [ No CAS ]
  • 75
  • [ 4943-86-6 ]
  • [ 119-67-5 ]
  • [ 1426431-46-0 ]
YieldReaction ConditionsOperation in experiment
86% With 2,2,2-trifluoroethanol; at 20℃; for 0.116667h;Green chemistry; General procedure: A mixture of an equimolar quantities of 2-aminobenzamides (1 mmol), 2-carboxybenzaldehyde (1 mmol) and TFE (0.5 mL) was ground together for 9-11 min using a mortar and pestle at room temperature. The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was washed with petroleum ether followed by CHCl3, and then filtered to obtain the pure products.
  • 76
  • [ 4943-86-6 ]
  • [ 24122-31-4 ]
  • 77
  • [ 620-02-0 ]
  • [ 4943-86-6 ]
  • C19H15ClN2O2 [ No CAS ]
  • 78
  • [ 119072-55-8 ]
  • [ 4943-86-6 ]
  • [ 98-80-6 ]
  • [ 19857-35-3 ]
  • 79
  • [ 5344-90-1 ]
  • [ 106-47-8 ]
  • [ 4943-86-6 ]
  • 80
  • [ 4943-86-6 ]
  • [ 100-52-7 ]
  • [ 19857-35-3 ]
  • 81
  • [ 4943-86-6 ]
  • [ 107-21-1 ]
  • [ 24122-31-4 ]
  • 82
  • [ 123-91-1 ]
  • [ 4943-86-6 ]
  • [ 24122-31-4 ]
  • 83
  • [ 271-58-9 ]
  • [ 106-47-8 ]
  • [ 4943-86-6 ]
  • 84
  • [ 4943-86-6 ]
  • [ 98-86-2 ]
  • 2-benzoyl-3-(4-chlorophenyl)quinazolin-4(3H)-one [ No CAS ]
  • 85
  • [ 4943-86-6 ]
  • 2-(4-chlorophenyl)-1-phenyl-1H-indazol-3(2H)-one [ No CAS ]
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