Home Cart Sign in  
Chemical Structure| 34529-06-1 Chemical Structure| 34529-06-1

Structure of 34529-06-1

Chemical Structure| 34529-06-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 34529-06-1 ]

CAS No. :34529-06-1
Formula : C10H11NO4
M.W : 209.20
SMILES Code : COC(=O)C1=CC=CC(N)=C1C(=O)OC
MDL No. :MFCD09029586
InChI Key :VEJKSNHPNFHCLF-UHFFFAOYSA-N
Pubchem ID :13399384

Safety of [ 34529-06-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 34529-06-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 4
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 53.41
TPSA ?

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

78.62 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.77
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

1.73
Log Po/w (WLOGP)?

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

0.85
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.

1.26
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

0.92
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.3

Water Solubility

Log S (ESOL):?

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

-2.26
Solubility 1.15 mg/ml ; 0.00551 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.

-3.0
Solubility 0.21 mg/ml ; 0.00101 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

-2.2
Solubility 1.33 mg/ml ; 0.00634 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.

-6.35 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

0.0
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

2.0 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)

1.73

Application In Synthesis of [ 34529-06-1 ]

* 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 [ 34529-06-1 ]

[ 34529-06-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 13365-26-9 ]
  • [ 34529-06-1 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;palladium on activated charcoal; In methanol; under 2844.39 Torr; [0030] The synthesis of mIBX is readily accomplished from commercially available 3-nitrophtalic acid as follows: esterification of 3-nitrophtalic acid via the corresponding acid chloride to give nitrodiester (100%), which upon catalytic hydrogenation provides the aminodiester (100%). Diazotization is then performed, followed by iodination of the aminodiester to provide dimethyl 3-iodophthalate in about 91 % yield. This is followed by saponification, then acidification of dimethyl 3-iodophthalate to give 3-iodophthalic acid in about 93 % yield. 3-iodophthalic acid is then oxidized to form the water-soluble MIBX. This process is carried out using KBrO3 in 0.73H2SO4 at 55-60 C. as follows: KBrO3 (5 g, 30 mmol) is added in portions to a suspension of 3-iodophthalic acid (5 g, 17.1 mmol) in 70 ML of 0.73 M H2SO4 over a period of 20 minutes; The mixture is then maintained at 55-60 C. for 12 hours and the resulting clear orange solution is evaporated to yield an off-white solid, which is triturated with 30 ML of water at 0 C. for 2 hours and filtered to obtain a white solid.This is further triturated with hexane (100 ML) for 6 hours and filtered to give MIBX (3.9 g, 71%) as a white solid with a melting point of 258-260 C. The approximately 70% yield for the conversion of 3-iodophthalic acid to MIBX is the isolated yield of MIBX, with the actual conversion near quantitative as evident from monitoring the oxidation of 3-iodophthalic acid to MIBX by 1H NMR spectroscopy. Water-soluble MIBX is isolated as an analytically pure white solid.The synthesis of MIBX from 3-nitrophthalic acid is illustrated in . The physical properties of MIBX are as follows: mp 258-260 C.; IR (KBr), 3503 3469, 3050, 1708, 1631, 1588, 1369, 730, 700 cm-1; 1H NMR (D2O), 300 MHz): δ 8.35 (dd, J=7.9, 1.0 Hz, 1H), 8.09 (t, J=7.9 Hz, 1H), 7.94 (dd, J=7.9, 1.0 Hz, 1H); 13C NMR (D2O, 75 MHz): δ 125.5, 127.5, 132.5, 134.7, 137.0, 147.1 (ring carbons), 168.9, 172.9 (carbonyl carbons).
93.7% With palladium 10% on activated carbon; hydrogen; In methanol; for 16h; (2) The <strong>[13365-26-9]dimethyl 3-nitrophthalate</strong> (239 mg, 1 mmol) obtained in the step (1) was dissolved in methanol (4 mL), and a catalytic amount of 10% Pd/C was added. Under the action of H2 (hydrogen balloon), after 16 hours of reaction, TLC detected the disappearance of <strong>[13365-26-9]dimethyl 3-nitrophthalate</strong>, Pd/C was removed by filtration, concentrated under reduced pressure, Drying a yellow solid (196 mg, yield 93.7%, HPLC purity 93.1%) is dimethyl 3-aminophthalate; by recrystallization or silica gel column chromatography, dimethyl 3-aminophthalate having a purity of ≥99% can be obtained.
90% With palladium 10% on activated carbon; hydrogen; In ethanol; (3) Synthesis of dimethyl 3-aminophthalate (compound 4) Dimethyl 3-nitrophthalate (18.1 g, 75.7 mmol) from step (2) was dissolved in 400 mL ethanol and 10% Pd/C (50% water, 1.8 g) was added. The reaction mixture was stirred overnight under a hydrogen atmosphere. The reaction mixture was filtered, and the filter cake was wash with ethanol. Ethanol was removed to give compound 4 as a yellow solid (14.2 g, 90%).
86% 5.40.2 3-Aminophthalic Acid Dimethyl Ester A mixture of 3:1 ethanol-conc. HCl (200 mL) was cooled to 0 C. and then 3-nitrophthalic acid dimethyl ester (15.0 g, 62.8 mmol) was added. Maintaining the cooling, tin chloride (70.8 g, 314 mmol) was added portionwise, over a period of 15 minutes. Following completion of the addition, the cooling bath was removed, and stirring proceeded at room temperature. After 2 hours, the mixture was neutralized by the addition of solid sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate (3×150 mL) and the combined extracts were washed with water (5×250 mL), were dried (MgSO4) and evaporated, providing 11.3 g of the product as a yellow oil in 86% yield: 1H NMR (CDCl3) δ 3.84 (s, 3H), 3.86 (s, 3H), 5.20 (br, 2H), 6.78 (dd, J=8.5 Hz, J=1.0 Hz, 1H), 6.90 (dd, 1H, J=7.3 Hz, J=1.0 Hz, 1H), 7.24 (t, J=7.8 Hz, 1H).
86% Step 2:[163] A mixture of 3:1 ethanol-conc. HCl (200 mL) was cooled to 0 0C and then 3- nitrophthalic acid dimethyl ester (15.0 g, 62.8 mmol) was added. Maintaining the cooling, tin (II) chloride (70.8 g, 314 mmol) was added portionwise, over a period of 15 min. Following completion of the addition, the cooling bath was removed and stirring proceeded at room temperature. After 2 h, the mixture was neutralized by the addition of solid sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate (3 x 150 mL) and the combined extracts were washed with water (5 x 250 mL), were dried (MgSO4) and evaporated, providing 11.3 g of 3-aminophthalic acid dimethyl ester as a yellow oil, in 86% yield; 1H NMR (CDCl3) δ 3.84 (s, 3H), 3.86 (s, 3H), 5.20 (br, 2H), 6.78 (dd, J = 8.5 Hz, J = 1.0 Hz, IH), 6.90 (dd, IH, J = 7.3 Hz, J = 1.0 Hz, IH), 7.24 (t, J = 7.8 Hz, IH).
83% With hydrogenchloride; In methanol; water; REFERENCE EXAMPLE 102 Dimethyl 3-aminophthalate Dimethyl 3-nitrophthalate (18.0 g, 75.2 mmol) obtained in Reference Example 101 was dissolved in a mixture of concentrated hydrochloric acid (50.0 ml) water (250 ml) and methanol (25.0 ml), and an excess of zinc powder was added in portions. After completion of the reaction, the reaction mixture was filtered, and the filtrate was made basic with 25% aqueous ammonium hydroxide, and extracted with ethyl acetate. After the extract was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residue was subjected to a column chromatography on a silica gel eluding with n-hexane-ethyl acetate (10:1, v/v) to give the title compound (13.1 g, 83%) as an oil. 1H-NMR (CDCl3) δ: 3.85 (3H, s), 3.86 (3H, s), 5.20 (2H, bs), 6.78 (1H, dd, J=8.4, 1.2 Hz), 6.90 (1H, dd, J=7.4, 0.8 Hz), 7.24 (1H, d, J=8.0 Hz).
18.1 g (87%) With hydrogen;palladium-carbon; In ethyl acetate; Methyl-3-amino-2-(methoxycarbonyl)benzoate To a solution of methyl-2-(methoxycarbonyl)-3-nitrobenzoate (23.8 g, 99.51 mmol) in ethyl acetate (200 ml) was added 10% Pd/C (1.8 g). The mixture was hydrogenated under 50 psi of hydrogen for 3 hours in a Parr Type Shaker. The mixture was filtered through Celite and the filtrate was concentrated in vacuo to yield an oil. The crude product was purified by flash chromatography (dichloromethane/ethyl acetate 95 to 5) to afford 18.1 g (87%) of the product as a brown oil: 1H NMR (CDCl3) δ7.22 (t, J=7.6 Hz, 1H), 6.90 (d, J=7.2 Hz, 1H), 6.79 (d, J=8.7 Hz), 5.07 (b, 2H), 3.85 (s, 3H), 3.83 (s, 3H).
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 2327.23 Torr; Preparation of 3-amino-phthalic Acid Dimethyl Ester, 3 The compound 2 (205 g, 1.0 mol) was dissolved in 2 L of MeOH. Catalytic 10% Pd/C was added and the solution was hydrogenated under H2 (45 psi) on a Parr hydrogenation apparatus at room temperature overnight. Filtered through celite and evaporated to give a quantitative yield of 3-amino-phthalic acid dimethyl ester, 3. 1H NMR (300 MHz, DMSO-d6): 7.26 (t, J=7.33 Hz, 1H), 6.94 (d, J=8.34 Hz, 1H), 6.77 (d, J=8.33 Hz, 1H), 6.12 (s, 2H), 3.77 (s, 3H), 3.76 (s, 3H). 13C NMR: 51.51, 51.77, 110.50, 115.16, 118.56, 131.26, 133.16, 148.28, 167.12, 168.11.
With palladium 10% on activated carbon; hydrogen; In acetone; at 20℃; under 3102.97 Torr; for 5h; Dissolve Compound 1 (500mg) in acetone (30mL) solution, transfer to a hydrogenation reaction flask, add Pd / C (40mg, 10%), build a hydrogenation device, and react at 60psi for 5h at room temperature. , Remove the device, remove Pd / C by suction filtration, condense at low temperature by rotary evaporation, extract with ethyl acetate (30mLx3), combine the organic layers, wash once with saturated brine, add anhydrous magnesium sulfate to dry, and dry by suction filtration to obtain crude product. Column chromatography to obtain intermediate 2

  • 2
  • [ 34270-90-1 ]
  • [ 34529-06-1 ]
  • [ 34529-07-2 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 34529-06-1 ]

Aryls

Chemical Structure| 18583-89-6

A298337 [18583-89-6]

Methyl 3-amino-2-methylbenzoate

Similarity: 0.98

Chemical Structure| 21339-74-2

A120984 [21339-74-2]

Methyl 4-amino-2,5-dimethylbenzoate

Similarity: 0.96

Chemical Structure| 79909-92-5

A177972 [79909-92-5]

Methyl 4-amino-2,6-dimethylbenzoate

Similarity: 0.96

Chemical Structure| 841296-15-9

A172824 [841296-15-9]

Methyl 4-amino-3-formylbenzoate

Similarity: 0.92

Chemical Structure| 18595-16-9

A199903 [18595-16-9]

Methyl 2-amino-5-methylbenzoate

Similarity: 0.92

Esters

Chemical Structure| 18583-89-6

A298337 [18583-89-6]

Methyl 3-amino-2-methylbenzoate

Similarity: 0.98

Chemical Structure| 21339-74-2

A120984 [21339-74-2]

Methyl 4-amino-2,5-dimethylbenzoate

Similarity: 0.96

Chemical Structure| 79909-92-5

A177972 [79909-92-5]

Methyl 4-amino-2,6-dimethylbenzoate

Similarity: 0.96

Chemical Structure| 841296-15-9

A172824 [841296-15-9]

Methyl 4-amino-3-formylbenzoate

Similarity: 0.92

Chemical Structure| 18595-16-9

A199903 [18595-16-9]

Methyl 2-amino-5-methylbenzoate

Similarity: 0.92

Amines

Chemical Structure| 18583-89-6

A298337 [18583-89-6]

Methyl 3-amino-2-methylbenzoate

Similarity: 0.98

Chemical Structure| 21339-74-2

A120984 [21339-74-2]

Methyl 4-amino-2,5-dimethylbenzoate

Similarity: 0.96

Chemical Structure| 79909-92-5

A177972 [79909-92-5]

Methyl 4-amino-2,6-dimethylbenzoate

Similarity: 0.96

Chemical Structure| 841296-15-9

A172824 [841296-15-9]

Methyl 4-amino-3-formylbenzoate

Similarity: 0.92

Chemical Structure| 18595-16-9

A199903 [18595-16-9]

Methyl 2-amino-5-methylbenzoate

Similarity: 0.92