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Structure of 50413-30-4

Chemical Structure| 50413-30-4

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Product Details of [ 50413-30-4 ]

CAS No. :50413-30-4
Formula : C9H11NO3
M.W : 181.19
SMILES Code : COC(=O)C1=C(N)C=C(OC)C=C1
MDL No. :MFCD06658470
Boiling Point : No data available
InChI Key :CEKCJQBZVNIMLD-UHFFFAOYSA-N
Pubchem ID :12919999

Safety of [ 50413-30-4 ]

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

Computational Chemistry of [ 50413-30-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 48.62
TPSA ?

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

61.55 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.72
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

2.64
Log Po/w (WLOGP)?

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

1.07
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.

1.06
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

0.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.5

Water Solubility

Log S (ESOL):?

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

-2.77
Solubility 0.308 mg/ml ; 0.0017 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-3.58
Solubility 0.0473 mg/ml ; 0.000261 mol/l
Class?

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

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

-2.24
Solubility 1.04 mg/ml ; 0.00573 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

Yes
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.

-5.53 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)

1.41

Application In Synthesis of [ 50413-30-4 ]

* 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 [ 50413-30-4 ]

[ 50413-30-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 108-30-5 ]
  • [ 50413-30-4 ]
  • [ 108489-18-5 ]
  • 2
  • [ 50413-30-4 ]
  • [ 144-62-7 ]
  • 2-hydroxyoxalylamino-4-methoxy-benzoic acid methyl ester [ No CAS ]
  • 3
  • [ 50413-30-4 ]
  • [ 77287-34-4 ]
  • [ 16064-24-7 ]
  • 5
  • [ 67-56-1 ]
  • 2-Amino-4-methoxy-benzoyl chloride [ No CAS ]
  • [ 50413-30-4 ]
  • 6
  • [ 50413-30-4 ]
  • [ 98-59-9 ]
  • [ 93009-62-2 ]
YieldReaction ConditionsOperation in experiment
70% With pyridine; at 20℃; for 16h; To a stirred solution of compound If-I (7 g, 38.6 mmol) in pyridine (80 ml) was slowly added TsCI (8.8 g, 46.6 mmol) at rt. This solution was further stirred for 16h. The reaction mixture was poured into cold water upon which a solid was formed. The precipitate was filtered off and washed with n-pentane (50 ml) to afford the title compound If-2 as an off-white solid (10.8 g, 70% yield). LCMS [M+H] 336.
  • 7
  • [ 67-56-1 ]
  • [ 4294-95-5 ]
  • [ 50413-30-4 ]
YieldReaction ConditionsOperation in experiment
75.92% With sulfuric acid; for 24h;Reflux; To a solution of 2-amino-4-methoxybenzoic acid 33 (5.0 g,0.03 mol) in methanol (50 mL) was added strong sulphuricacid (9 mL). The solution was stirred at reflux for 24 h. Itwas cooled to room temperature and the pH of the mixturewas adjusted to 5~6 with saturated sodium carbonatesolution. The solution was extracted with EA (100 mL*2).The combined organic layers were washed with brine(50 mL), dried over Na2SO4, filtered and concentrated,affording white powder 34 (4.11 g, 75.92%). 34: 1H NMR (400 MHz, CDCl3) 7.81 (d, J = 8.9 Hz, 1 H), 6.25 (dd, J =9.0, 2.5 Hz, 1H), 6.13 (d, J = 2.4 Hz, 1H), 5.80 (s, 2H), 3.86(s, 3H), 3.81 (s, 3H).
37% With sulfuric acid;Reflux; Step a): Methyl 2-amino-4-methoxybenzoate 1000 mg (6.0 mmol) of 2-amino-4-methoxybenzoic acid are reacted according to General Method I. Yield: 400 mg (37% of theory) LC-MS (Method 3): Rt=1.96 min; MS (ESIpos): m/z=182 [M+H]+. 5 mmol of the carboxylic acid are dissolved in 50 ml of methanol, and 5 ml of concentrated sulfuric acid are added. The mixture is heated under reflux for 14-24 h. After cooling to room temperature, the solution is poured onto ice and adjusted to pH 6 using sodium bicarbonate. After addition of 100 ml of dichloromethane, the aqueous phase is separated off and reextracted twice with in each case 50 ml of dichloromethane. The combined organic extracts are dried over sodium sulfate, filtered and concentrated under reduced pressure.
  • 8
  • [ 67-56-1 ]
  • 2-amino-4-methoxy-benzoic acid-hydrochloride [ No CAS ]
  • [ 50413-30-4 ]
  • 9
  • [ 50413-30-4 ]
  • [ 4637-24-5 ]
  • 2-(dimethylamino-methyleneamino)-4-methoxy-benzoic acid methyl ester [ No CAS ]
  • 12
  • [ 50413-30-4 ]
  • 7-hydroxy-4-oxo-1,4-dihydro-quinoline-3-carbonitrile [ No CAS ]
  • 13
  • [ 50413-30-4 ]
  • 4-chloro-7-(3-chloro-propoxy)-quinoline-3-carbonitrile [ No CAS ]
  • 14
  • [ 50413-30-4 ]
  • 7-(3-chloro-propoxy)-4-oxo-1,4-dihydro-quinoline-3-carbonitrile [ No CAS ]
  • 15
  • [ 50413-30-4 ]
  • 7-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile [ No CAS ]
  • 16
  • [ 50413-30-4 ]
  • 7-(3-chloro-propoxy)-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile [ No CAS ]
  • 17
  • [ 50413-30-4 ]
  • 7-(3-morpholin-4-yl-propoxy)-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile [ No CAS ]
  • 18
  • [ 52351-75-4 ]
  • [ 50413-30-4 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; sodium ethanolate; In methanol; water; (c) Methyl 4-methoxy-anthranilate One hundred fifty-eight grams (0.89 mol) of 6-methoxy-isatine are suspended in 1300 ml of methanol and mixed with a solution of 54 gm (1.34 mol) of sodium ethoxide in 500 ml of methanol. One hundred eight milliliters (1.07 mol) of 30% hydrogen peroxide are added thereto dropwise, under stirring, and the resulting mixture is stirred for 30 minutes. The contents of the flask are concentrated down to half their volume, mixed with water, and adjusted to a pH of 5 to 6 with glacial acetic acid. After extraction with methylene chloride, the mixture is subjected to suction filtration, kieselguhr being used, and dried with sodium sulfate, and the solvent is distilled off. The residue is recrystallized from petroleum ether/cyclohexane (2:1). M.p: 80-82 C., Yield: 109 gm (67.7% of theory). The following compounds are prepared by analogous procedures:
  • 20
  • [ 50413-30-4 ]
  • 8-methoxy-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one [ No CAS ]
  • 27
  • [ 50413-30-4 ]
  • (4aS,11bS)-9-Methoxy-4-propyl-7-(toluene-4-sulfonyl)-2,3,4,4a,5,6,7,11b-octahydro-1-oxa-4,7-diaza-dibenzo[a,c]cycloheptene [ No CAS ]
  • 28
  • [ 50413-30-4 ]
  • 4-Amino-5-(3-hydroxy-propyl)-8-methoxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol [ No CAS ]
  • 29
  • [ 50413-30-4 ]
  • 2,3,4,5-tetrahydro-8-methoxy-5-oxo-4-propionyloxyimino-1-(p-tolylsulfonyl)-1H-1-benzazepine [ No CAS ]
  • 30
  • [ 50413-30-4 ]
  • (4aS,11bS)-9-Methoxy-4-propyl-7-(toluene-4-sulfonyl)-4,4a,5,6,7,11b-hexahydro-1-oxa-4,7-diaza-dibenzo[a,c]cyclohepten-3-one [ No CAS ]
  • 33
  • [ 50413-30-4 ]
  • Chloro-acetic acid (4S,5S)-4-[(2-chloro-acetyl)-propyl-amino]-8-methoxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester [ No CAS ]
  • 34
  • [ 50413-30-4 ]
  • (4S,5S)-4-Amino-8-methoxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol [ No CAS ]
  • 35
  • [ 50413-30-4 ]
  • (4R,5S)-4-Amino-8-methoxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol [ No CAS ]
 

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Technical Information

Categories

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