Structure of 92-70-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 92-70-6 |
Formula : | C11H8O3 |
M.W : | 188.18 |
SMILES Code : | C1=C2C(=CC(=C1C(O)=O)O)C=CC=C2 |
MDL No. : | MFCD00004103 |
InChI Key : | ALKYHXVLJMQRLQ-UHFFFAOYSA-N |
Pubchem ID : | 7104 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312-H315-H319-H361-H371-H317-H412 |
Precautionary Statements: | P501-P273-P272-P260-P270-P202-P201-P264-P280-P337+P313-P305+P351+P338-P308+P311-P362+P364-P333+P313-P301+P312+P330-P302+P352+P312-P405 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 52.93 |
TPSA ? Topological Polar Surface Area: Calculated from |
57.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.41 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.24 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.84 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.11 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.39 |
Solubility | 0.0765 mg/ml ; 0.000407 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.92 |
Solubility | 0.0224 mg/ml ; 0.000119 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.87 |
Solubility | 0.252 mg/ml ; 0.00134 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.28 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.01 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; | Pamoic acid may be prepared by condensing commercially available 3 -hydroxy-2 -naphthoic acid (Acros Organics, Fairlawn, NJ) with formaldehyde or paraformaldehyde in the presence of sodium hydroxide (Strohbach, 1901, Chem. Ber. 34:4148; Hosaeus, 1892, Chem. Ber.25:3215; Brass, 1928, Chem. Ber. 61 :1001), as shown in Scheme I. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In water; chlorobenzene; toluene; at 85℃; for 5h; | 1. 1 part of the material 2-hydroxy-3-naphthoic acid (the amount of the substance,The same below) dissolved in water and immiscible solvent 1.1 (such as toluene, chlorobenzene),The solution was added to the reactor (Figure 1),Then, 1.15 parts of 2,5-dimethoxy-4-chloroaniline was added,The reaction mixture was heated at a temperature of 85 C,The reaction time was 5h, and the crude product was obtained in 89% yield.2. Distillation of crude products, the yield of 94%.3. Add the refined product to a separate dryer (Figure 2)The rising steam is evenly contacted with the crude phenol concentrate through the steam distributor,Water vapor cold liquid liquefaction into small water droplets, dissolved products in the soluble impurities,Excessive steam is condensed at the top of the condenser to form a stream of water into the desiccator to rinse the phenolic AS-LC product,After repeated rinsing three times, finally, in the jacket outside the dryer through the water vapor,The dryer was dried by heating to give the final product in a yield of 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; calcium chloride; sodium nitrite; In water; | EXAMPLE 1 A solution of 24.2 grams (0.1294 mole) of pure 6-amino-m-toluenesulfonic acid and 1.2 grams (0.0054 mole) of 2-naphthylamine-1-sulfonic acid is prepared in 500 ml of water by adding 57 ml of a 10% solution of sodium hydroxide and adjusting the pH to 11.5. A solution of 35.6 grams of calcium chloride and 1.5 grams of strontium nitrate in 100 ml of water is added thereto and the mixture cooled to 0 C. with ice. The amines are diazotized by adding 35 ml (0.14 mole) of 4 N sodium nitrite, followed by 150 ml (0.411 mole) of 10% hydrochloric acid. The mixture is stirred for about 3 minutes at 0 C., while maintaining excess nitrous acid. 2-Hydroxy-3-naphthoic acid (28.0 grams, 0.1489 mole) is dissolved in 500 ml of water by adding 180 ml of 10% sodium hydroxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 25 - 50℃; for 20.0h; | Example 7; Preparation of Imipramine XinafoateTo a solution containing 7.7 g of 3-hydroxy-2-napthoic acid in 75.0 g of USP water was added as necessary dilute HCl or NaOH solution to adjust the solution to about pH 9.4. To a second solution of 13.6 g of <strong>[113-52-0]imipramine HCl</strong> in 100.0 g of USP water was added as necessary dilute HCl or NaOH solution to adjust the solution to about pH 4.5. The <strong>[113-52-0]imipramine HCl</strong> solution was added to the 3-hydroxy-2-napthoic sodium salt solution over a period of about 2 h. The mixture was stirred and held at around 50 C. for at least 18 h. The mixture was cooled to below 25 C. and the solids were collected by filtration. The solid cake was washed with USP water (2×100 g). The solid cake was dried at 105 C. under vacuum to yield a powder (12.7 g) and characterized by DSC (FIG. 13), FTIR (FIG. 14) and 1H NMR (FIG. 15). |