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Chemical Structure| 39549-79-6 Chemical Structure| 39549-79-6

Structure of 39549-79-6

Chemical Structure| 39549-79-6

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Product Details of [ 39549-79-6 ]

CAS No. :39549-79-6
Formula : C8H10N2O
M.W : 150.18
SMILES Code : O=C(N)C1=CC=C(C)C=C1N
MDL No. :MFCD00221474
Boiling Point : No data available
InChI Key :RUHKZVAPXHIWJH-UHFFFAOYSA-N
Pubchem ID :2801474

Safety of [ 39549-79-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H317-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 39549-79-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 2.0
Molar Refractivity 43.91
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

69.11 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.23
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.71
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.68
Log Po/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.

0.91
Log Po/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

0.71
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.85

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.56
Solubility 4.17 mg/ml ; 0.0278 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.74
Solubility 2.74 mg/ml ; 0.0182 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-2.0
Solubility 1.51 mg/ml ; 0.0101 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

No
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

No
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.

-6.71 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

1.0
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

1.0 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)

1.0

Application In Synthesis of [ 39549-79-6 ]

* 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 [ 39549-79-6 ]

[ 39549-79-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 64-18-6 ]
  • [ 39549-79-6 ]
  • [ 75844-40-5 ]
YieldReaction ConditionsOperation in experiment
91% at 100℃; for 6h; 2-amino-4-mthylbenzamide (4.93 g, 32.8 mmol) obtained in above was added with formic acid (30 mL, 787.9 mmol), followed by stirring for 6 hours at 100°C. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and washed with water. The filtered solid was dried with warm wind in an oven (40°C) for 6 hours or more to obtain the title compound (4.79 g, 91percent). 1H-NMR Spectrum (300 MHz, DMSO-rftf): delta 8.06 (s, 1H), 8.00 (d, 1H), 7.47 (s, 1H), 7.34 (d, 1H), 2.45 (s, 3H) MS(ESI+, m/z): 161 [M+H]+
91% at 100℃; for 6h; <strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (4.93 g, 32.8 mmol) obtained in <Step 1> above was added with formic acid (30 mL, 787.9 mmol), followed by stirring for 6 hours at 100° C. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and washed with water. The filtered solid was dried with warm wind in an oven (40° C.) for 6 hours or more to obtain the title compound (4.79 g, 91percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 8.06 (s, 1H), 8.00 (d, 1H), 7.47 (s, 1H), 7.34 (d, 1H), 2.45 (s, 3H) MS (ESI+, m/z): 161 [M+H]+
84% at 100℃; for 6h; A mixture of <strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (20 g, 133 mmol) and formic acid (120 ml, 3129 mmol) was heated to 100 0C for 6 h. The reaction was cooled to RT and the volatiles were removed under reduced pressure. The residue was then washed carefully with aqueous saturated sodium bicarbonate and then with water. The tan solid was then dried in a vacuum oven at 45 0C overnight to give 7-methylquinazolin-4(3H)-one (18.00 g, 84percent yield). MS (ESI, pos. ion) m/z: 161 [M+H]+
Example 332; Preparation of 7-methyIquinazolin-4(3H)-oneA mixture of <strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (20 g, 133 mmol)and formic acid (120 ml, 3129 mmol) was heated to 100 0C. After 6 hours, the reaction was cooled down to to RT and the volatiles were removed under reduced pressure. The residue was then washed carefully with aqueous saturated sodium bicarbonate and then with water. The tan solid <n="118"/>was then dried in a vacuum oven at 45 0C overnight to give 7-methylquinazolin-4(3H)- one. MS (M+H)+ 161.

  • 3
  • [ 39549-79-6 ]
  • [ 39145-59-0 ]
  • 2-(1<i>H</i>-benzimidazol-2-yl)-5-methyl-aniline [ No CAS ]
  • 4
  • [ 39549-79-6 ]
  • [ 636-24-8 ]
  • 5-methyl-2-(5-methyl-1(3)<i>H</i>-benzimidazol-2-yl)-aniline [ No CAS ]
  • 5
  • [ 39549-79-6 ]
  • 7-methylbenzo[d][1,2,3]triazin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% A suspension of 2-amino-5-methylbenzamide (404 mg, 2.7 mmol) in HCl (2N, 5 mL) at 0 C was treated with NaNO2 (208 mg, 3.0 mmol). The mixture was stirred for 1 h, then made basic with Na2CO3 (20 % soln). The resulting solid was collected via vacuum filtration to provide 249 mg (57 %) of the title compound as a brown solid. 1H EPO <DP n="53"/>NMR (DMSO-J6) delta 8.11 (d, 1 H), 7.96 - 8.00 (m, 1 H), 7.73 (ddd, 1 H), 2.56 (s, 3 H). MS (ES) 160 (M - H), 162 (M + H).
General procedure: A solution of anthranilamide (30 mmol) in 1N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirringat 0 C, 30% NaOH solution was added slowly to adjustp H value to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered, washed with deionized water (200 mL), and dried to afford compounds 10 in yields of 40-92%.
  • 7
  • [ 39549-79-6 ]
  • [ 541-41-3 ]
  • 2-ethoxycarbonylamino-4-methyl-benzoic acid amide [ No CAS ]
  • 8
  • [ 39549-79-6 ]
  • [ 108-24-7 ]
  • [ 194473-09-1 ]
  • 9
  • [ 39549-79-6 ]
  • [ 108-24-7 ]
  • [ 2305-36-4 ]
  • 4-methyl-2-(2,7-dimethyl-4-oxo-4<i>H</i>-quinazolin-3-yl)-benzoic acid [ No CAS ]
  • 4-methyl-2-(2,7-dimethyl-4-oxo-4<i>H</i>-quinazolin-3-yl)-benzoic acid amide [ No CAS ]
  • 10
  • [ 26830-96-6 ]
  • [ 39549-79-6 ]
YieldReaction ConditionsOperation in experiment
53% With sulfuric acid; In water; at 120℃; for 0.333333h; Concentrated sulfuric acid (3 mL) was carefully added to a suspension of 2- amino-4-methylbenzonitrile (800 mg, 6.1 mmol) in H2O (1 mL). The solution was then placed into an oil bath, pre-heated to 120 0C, the reaction stirred for 20 min and then immediately cooled in an ice bath. The solution was made basic via the addition of 5 percent NaOH and the resulting solid collected via vacuum filtration. 484.4 mg (53 percent) of the title compound as a light brown solid were obtained. 1H NMR (DMSO-dbeta) delta 7.63 (br s, 1 H), 7.42 (d, 1 H), 6.95 (br s, 1 H), 6.55 (br s, 2 H), 6.45 - 6.48 (m, 1 H), 6.29 (ddd, 1 H), 2.16 (s, 3 H). MS (ES) 134 (M - 16).
43% With potassium hydroxide; In ethanol; for 8h;Reflux; 2-amino-4-methylbenzonitrile (10 g, 75.7 mmol) was dissolved in ethanol, added with potassium hydroxide (21.2 g, 378 mmol), followed by refluxing for 8 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with a saturated aqueous solution of sodium bicarbonate and brine. The obtained organic layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethanol to obtain the title compound (4.9 g, 43percent). 1H-NMR Spectrum (300 MHz, DMSO- 6): delta 7.40 (d, 1H), 6.52 (s, 2H), 6.45 (s, 1H), 6.28 (d, lH), 2.14 (s, 3H)
43% With potassium hydroxide; In ethanol; for 8h;Reflux; 2-amino-4-methylbenzonitrile (10 g, 75.7 mmol) was dissolved in ethanol, added with potassium hydroxide (21.2 g, 378 mmol), followed by refluxing for 8 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with a saturated aqueous solution of sodium bicarbonate and brine. The obtained organic layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethanol to obtain the title compound (4.9 g, 43percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 7.40 (d, 1H), 6.52 (s, 2H), 6.45 (s, 1H), 6.28 (d, 1H), 2.14 (s, 3H)
  • 11
  • [ 39549-79-6 ]
  • [ 57-13-6 ]
  • [ 62484-15-5 ]
  • 14
  • [ 7647-01-0 ]
  • [ 26830-95-5 ]
  • tin [ No CAS ]
  • [ 39549-79-6 ]
  • 15
  • [ 39549-79-6 ]
  • sodium cyanate [ No CAS ]
  • 4-methyl-2-ureido-benzoic acid amide [ No CAS ]
  • 16
  • [ 39549-79-6 ]
  • 3-hydroxy-naphthoyl chloride-(2) [ No CAS ]
  • 2-(3-hydroxy-[2]naphthoylamino)-4-methyl-benzoic acid amide [ No CAS ]
  • 17
  • [ 65078-05-9 ]
  • [ 39549-79-6 ]
YieldReaction ConditionsOperation in experiment
1.2 g With iron; ammonium chloride; In ethanol; water; for 2h;Reflux; General procedure: To a solution of 5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-1-amine (1.0 g, 3.0 mmol) in a mixture of EtOH:H2O (8:2, 10 mL) were added iron powder (1.26 g, 4.8 mmol), and NH4Cl (1.6 g, 30.0 mmol). The reaction mass was heated at reflux for 2 h and filtered. The filtrate was concentrated and the residue was purified by column chromatography to afford 0.800 g of the title product. 1H NMR (300 MHz, DMSO-d6): delta 9.18 (s, 1H), 8.35 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.52 (t, J=7.8 Hz, 1H), 7.42-7.24 (m, 3H), 6.86 (d, J=7.5 Hz, 1H), 5.84 (s, 2H). The title compound was prepared following the procedure described in Step 3 of Intermediate-i using 4-methyl- 2-nitrobenzamide (1.60 g, 8.88 mmol), iron powder (2.97 g,53.33 mmol), and NH4C1 (2.85 g, 53.33 mmol) in EtOH (8 mE) and water (2 mE) to afford 1.2 g of the title product. 1HNMR (300 MHz, DMSO-d5): oe 7.62 (br s, 1H), 7.42 (d, J=7.8 Hz, 1H), 6.93 (br s, 1H), 6.53 (s, 2H), 6.46 (s, 1H), 6.29 (d, J=7.8 Hz, 1H), 2.15 (s, 3H).
  • 18
  • [ 39549-79-6 ]
  • [ 4521-61-3 ]
  • N-(2-Carbamoyl-5-methyl-phenyl)-3,4,5-trimethoxy-benzamide [ No CAS ]
  • 19
  • [ 39549-79-6 ]
  • [ 610-14-0 ]
  • [ 874285-98-0 ]
  • 20
  • [ 39549-79-6 ]
  • 6,11-dimethyl-5,6-dihydroquinazolino[4,3-b]quinazolin-8-one [ No CAS ]
  • 21
  • [ 39549-79-6 ]
  • 11-methyl-6-phenyl-5,6-dihydroquinazolino[4,3-b]quinazolin-8-one [ No CAS ]
  • 22
  • [ 39549-79-6 ]
  • [ 30391-09-4 ]
  • 27
  • [ 39549-79-6 ]
  • [ 25171-19-1 ]
  • 29
  • [ 39549-79-6 ]
  • <i>N</i>,<i>N</i>-diethyl-<i>N</i>'-(2-chloro-7-methyl-quinazolin-4-yl)-ethylenediamine [ No CAS ]
  • 30
  • [ 24920-35-2 ]
  • [ 39549-79-6 ]
  • 31
  • [ 39549-79-6 ]
  • [ 590-86-3 ]
  • [ 1086673-11-1 ]
  • 32
  • [ 5390-04-5 ]
  • [ 39549-79-6 ]
  • [ 1208003-30-8 ]
  • 33
  • [ 131002-03-4 ]
  • [ 39549-79-6 ]
  • 34
  • [ 39549-79-6 ]
  • 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione [ No CAS ]
  • [ 1241915-26-3 ]
YieldReaction ConditionsOperation in experiment
91% With hydrogenchloride; sodium methylate; In tetrahydrofuran; methanol; Step A:To a solution of <strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (3 g, 20.0 mmol) in THF (40 mL) was added 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione from Example 16 (4.7 g, 24 mmol) and the solution was stirred for 2 hrs at 50° C. Sodium methoxide in MeOH (25percent, 5.2 mL, 24 mmol) was then added and the solution was stirred at 50° C. overnight.The reaction mixture solution was concentrated, 2N HCl was added and the mixture was filtered.The collected solid was dried to give 2-((4-fluorophenyl)(hydroxy)methyl)-7-methylquinazolin-4-ol (5.14 g, 91percent) which was used without further purification. LC-MS (ESI) m/z 285 (M+H)+.
00319] Step A: To a solution of <strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (3 g, 20.0 mmol) in THF (40 mL) was added 5-(4-fluorophenyl)-l,3-dioxolane-2,4-dione from Example 16 (4.7 g, 24 mmol) and the solution was stirred for 2 h at 50 0C. Sodium methoxide in MeOH (25percent, 5.2 mL, 24 mmol) was then added and the solution was stirred at 50 0C overnight. The reaction mixture solution was concentrated, 2N HCl was added and the mixture was filtered. The collected solid was dried to give 2-((4- fluorophenyl)(hydroxy)methyl)-7-methylquinazolin-4-ol (5.14 g, 91percent) which was used without further purification. LC-MS (ESI) m/z 285 (M + H)+.
  • 35
  • [ 1241914-79-3 ]
  • [ 39549-79-6 ]
  • [ 1241915-31-0 ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine; In 1,2-dichloro-ethane; at 20℃; 00325] Step B: To a solution of 2-(2,2-difluoro-2-(4-fluorophenyl)acetamido)-4- methylbenzamide (5.85 g, 0.0181 mol) in DCE (120 mL) were added TEA (91.5 mL, 0.724 mol) and chlorotrimethylsilane (34.4 mL, 0.272 mol) at rt. The reaction mixuture was stirred at 85 0C overnight. After cooling to rt, the solid was filtered and the filtrate was concentrated to dryness. The residue was taken in a mixture of EtOAc/THF (1: 1) and washed with water and brine. Pure product was obtained after crystallization from hot EtOAc (2.02 g, 37percent); LC-MS (ESI) m/z 305 (M+H)+.
 

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Technical Information

Categories

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