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CAS No. : | 104670-74-8 | MDL No. : | MFCD11042862 |
Formula : | C8H8BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FGSIUBWPZRBMOC-UHFFFAOYSA-N |
M.W : | 230.06 | Pubchem ID : | 11615550 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.83 |
TPSA : | 52.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 2.0 |
Log Po/w (XLOGP3) : | 2.57 |
Log Po/w (WLOGP) : | 1.83 |
Log Po/w (MLOGP) : | 2.06 |
Log Po/w (SILICOS-IT) : | 1.65 |
Consensus Log Po/w : | 2.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.12 |
Solubility : | 0.173 mg/ml ; 0.000753 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.32 |
Solubility : | 0.111 mg/ml ; 0.000482 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.97 |
Solubility : | 0.244 mg/ml ; 0.00106 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.48 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
95% | at 80℃; for 24 h; | Example 1 : Synthesis of 3-(3-methylsulfamoyl-phenylethynyl)-2-pyrrol- 1-yl -benzoic acid 2-Amino-3-bromo-benzoic acid methyl ester: 2-Amino-3-bromo-benzoic acid (5 g, 23 mmol) was dissolved in methanol (30 mL), concentrated sulfuric acid (1 mL) was added dropwise and the reaction mixture was refluxed at 80 °C for 24 hours, allowed to cool to ambient temperature and then concentrated at reduced pressure. The residue was diluted by water (10 mL) and basified with saturated sodium bicarbonate solution, extracted by ethyl acetate (20 mL x 3). The organic layer was dried (anhydrous magnesium sulfate), concentrated and purified by column chromatography through a silica gel cartridge (80 g) eluting with ethyl acetate/hexane (10percent) to give the product as a colorless oil (5 g, 95percent). |
91% | Stage #1: for 31 h; Reflux Stage #2: With sodium hydrogencarbonate In water |
2-ammo-3-bromobenzoic acid { 1.00 g) was mixed with methanol ( 10 ml ) and concentrated sulfuric acid (ImI). The mixture was stirred at reflux for 31 hours. The solvent were evaporated, and saturated aqueous sodium bicarbonate was carefully added. The solid was extracted with CHCl; (3x). The combined extracts were dried over Na-SOα and the solvents removed //; vacuo to afford methyl 2-amino-3-bromoben/oate as a semi -crystal line solid (976 mg, 91percent yield). LCMS (ES): >85° pure, m/z 230 [M+ 1]". |
91% | for 31 h; Reflux | 2-amino-3-bromobenzoic acid (1.00 g) was mixed with methanol (10 ml) and concentrated sulfuric acid (1 ml). The mixture was stirred at reflux for 31 hours. The solvent were evaporated, and saturated aqueous sodium bicarbonate was carefully added. The solid was extracted with CH2Cl2 (3.x.). The combined extracts were dried over Na2SO4 and the solvents removed in vacuo to afford methyl 2-amino-3-bromobenzoate as a semi-crystalline solid (976 mg, 91percent yield). LCMS (ES): >85percent pure, m/z 230 [M+1]+. |
55% | at 90℃; for 6 h; | To a stirred solution of 2-amino-3-bromobenzoic acid (78) (500 mg, 2.30 mmol) in methanol (10mL) was added sulfuric acid (1.90 mL, 3.50 mmol) at ambient temperature. After stirred for 6 h at90 °C, the whole was concentrated. The resulting residue was partitioned between dichloromethaneand water and the water layer was extracted with dichloromethane. The organic layer was washedwith saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and concentrated.Column chromatography (n-hexane/ethyl acetate = 5/1) gave the title compound (163 mg, 710 μmol,55percent) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With N-Bromosuccinimide In acetic acid at 20℃; | N-Bromosuccinimide (NBS, 1.960 g, 11.0 mmol) was added portionwise to a stirred solution of 2-aminobenzoic acid ester (1.511 g, 10.0 mmol) dissolved in acetic acid (16 ml) and the reaction mixture was stirred overnight at room temperature. The mixture was added with H2O and extracted with EtOAc (3×20 mL). The combined organic extract was washed with brine, dried over MgSO4, and the solvent was evaporated. The residue was purified by column chromatography (petroleum ether/CHCl3 = 2:1) to give the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | at 0 - 20℃; for 0.5 h; | 144D. Methyl 2-Amino-3-bromo-benzoate.; Trimethylsylildiazomethane (2M solution in THF, 5.6 mL, 13.4 mmol) was added to a solution of 2-Amino-3-bromo-benzoic acid from example 144B (2.32 g, 11.1 mmol) in 1 mL of dry THF at 0° C. After 30 minutes at room temperature, the reaction mixture was concentrated and the crude residue was purified by flash chromatography on SiO2 using Pet. Et./AcOEt 99:1 then 96:4 to afford a white solid (2.23 g, 86percent). NMR 1H (ppm, CDCl3): 7.83 (d, J3=7.97 Hz, 1H), 7.55 (d, J3=7.7 Hz, 1H), 6.51 (t, J3=7.9 Hz, 1H), 3.87 (s, 3H). MS (+ESI): M+H+ 230.0. |
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