Structure of 154257-76-8
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CAS No. : | 154257-76-8 |
Formula : | C7H3Cl2FO2 |
M.W : | 209.00 |
SMILES Code : | ClC1=C(C(=O)O)C=CC(=C1Cl)F |
MDL No. : | MFCD09835200 |
InChI Key : | KPFXMYOQAANDKH-UHFFFAOYSA-N |
Pubchem ID : | 10330705 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.38 |
TPSA ? Topological Polar Surface Area: Calculated from | 37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.34 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 2.8 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 3.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 3.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 2.94 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 2.71 |
Log S (ESOL):? ESOL: Topological method implemented from | -3.2 |
Solubility | 0.131 mg/ml ; 0.000625 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -3.24 |
Solubility | 0.12 mg/ml ; 0.000575 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.29 |
Solubility | 0.107 mg/ml ; 0.000514 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 | -5.59 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 | 0.0 |
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 | 1.0 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) | 1.69 |
* 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 |
---|---|---|
sBuLi (97 mL, 126 mmol) was dissolved in tetrahydrofuran (THF) (200 ml.) at -78 0C and TMEDA (19.02 mL, 126 mmol) was added. 3-chloro-4-fluorobenzoic acid (10 g, 57.3 mmol, commercially available from e.g. Sigma-Aldrich, Fluorochem or Apollo) dissolved in tetrahydrofuran (THF) (50 mL) was added dropwise at -78 0C and the solution stired at this temperature for 30 minutes. Hexachloroethane (54.2 g, 229 mmol) dissolved in tetrahydrofuran (THF) (200 mL) was added dropwise and the solution stirred to room temperature over 4 hours. Water (25 mL) was added and the solution concentrated in vacuo. The residue was partitioned between diethyl ether (300 mL) and saturated sodium bicarbonate solution (50 mL) and extracted with saturated sodium bicarbonate solution (3 x 50 mL). The aqueous phase was acidified to pH1 with 5N hydrochloric acid, extracted with diethyl ether (3 x 200 mL), combined extracts dried over anhydrous magnesium sulfate and concentrated in vacuo to afford a crude solid (9.21 g). The crude solid was recrystalised from heptane/diethyl ether to afford the desired product in 4.91 g. LC/MS = 207/209/211 (M-H)-, retention time = 0.88 minutes (2 minute method). The mother liquors were concentrated in vacuo, washed with heptane and dried to afford a second batch of desired product in 2.62 g LC/MS = 207/209/211 (M-H)-, retention time = 0.88 minutes (2 minute method). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; | <strong>[154257-76-8]2,3-dichloro-4-fluorobenzoic acid</strong> (I32) (5.76 g, 27.6 mmol) was suspended in dichloromethane (DCM) (150 mL) at O0C and treated with oxalyl chloride (2.89 mL, 33.1 mmol). The mixture was stirred at O0C for 10 minutes before 5 drops of DMF were added. The mixture was stirred to room temperature over 4 h. Solvents were removed in vacuo and the residue was azeotroped with toluene (3 x 100 ml_). The residue was used directly in subsequent steps without further purification, assuming 100% yield. |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1.0h; | Preparation 3 tert-Butyl (3S)-3-[cyclopentyl(2,3-dichloro-4-fluoro-benzoyl)amino]pyrrolidine-1-carboxylate Oxalyl chloride (2.13 ml, 24.4 mmol) was added to a suspension of <strong>[154257-76-8]2,3-dichloro-4-fluoro benzoic acid</strong> (4.25 g, 20.33 mmol) (see EP0600317, example 15) in dry dichloromethane (41 ml) at room temperature under nitrogen. N,N-dimethylformamide (80 l, 1 mmol) was added and the reaction mixture stirred for 1 hour. Solvent was removed by evaporation under reduced pressure to produce a yellow solid, which was dissolved in dichloromethane (20 ml) and added dropwise to solution of triethylamine (4.72 ml, 33.9 mmol) and the amine of preparation 1 (4.31 g, 16.95 mmol) in dichloromethane (36 ml) under nitrogen. After stirring for 18 hours at room temperature, the resultant mixture was diluted with dichloromethane (100 ml) and 1M aqueous potassium carbonate (90 ml). The organic phase was dried over magnesium sulfate, filtered and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in minimum quantity of dichloromethane and purified by chromatography on silica gel eluting with a solvent gradient of pentane changing to ethyl acetate: pentane (20:80, by volume) to produce the title compound as a white foam, 6.6 (73%). 1HNMR(CD3OD, 400 MHz, rotamers) delta: 1.43-1.47(d, 9H), 1.62(m, 1.5H), 1.72(m, 3H), 1.88(m, 1.5H), 1.97(m, 0.5H), 2.13(m, 1.5H), 2.32(m, 0.5H), 2.74(m, 1H), 3.40(m, 1H), 3.51-3.59(m, 1.5H), 3.76(m, 2H), 3.88(m, 1H), 4.05(m, 1H), 7.33(m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium dichromate; sulfuric acid; In acetic acid; at 100℃; for 2.0h; | (ii) 2,3-dichloro-1-fluoro-4-methylbenzene (0.090 g, 0.5 mmol) was added to a stirred mixture of potassium dichromate (0.284 g, 1 mmol) in acetic acid (1 ml). 97% Sulphuric acid (0.5 ml) was then added slowly to the mixture which was subsequently heated at 100 C. for 2 hrs. After cooling to room temperature, water and ice were added and the green solid thus obtained was filtered off and washed with cold water to afford 2,3-dichloro-4-fluorobenzoic acid (0.056 g, 0.27 mmol) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(iii) A solution of <strong>[154257-76-8]2,3-dichloro-4-fluorobenzoic acid</strong> (0.200 g, 0.92 mmol) in dichloromethane (~4 ml) was treated with 1-hydroxybenzotriazole (0.162 g, 1.2 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.230 g, 1.2 mmol), and triethylamine (0.56 ml, 4.0 mmol) under argon at room temperature. The mixture was stirred at room temperature for 40 minutes then treated with) 32% aqueous ammonium hydroxide (0.088 ml) and stirred overnight at room temperature. The mixture was diluted with dichloromethane and washed sequentially with water and then with saturated aqueous sodium hydrogen carbonate. The organic layer was separated and dried over sodium sulphate then concentrated to give 2,3-dichloro-4-fluorobenzamide (0.156 g) as a white solid that was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; | Example 1A 2,3-Dichloro-4-fluoro-N-methoxy-N-methyl-benzamide To a solution of 2,3-dichloro-4-fluoro- benzoic acid (prepared from 3-chloro-4-fluorobenzoic acid according to the literature: Bennetau et al. (1995) J CHEM. SOC., PERKIN TRANS. 1 1265-1271, 0.500 g, 2.39 mmol), O, N-dimethyl-hydroxylamine hydrochloride (0.467 g, 4.79 mmol), triethylamine (1.33 mL 9.57 mmol), and HOBt (0.733 gm 4.79 mmol) in DMF (10 mL) was added EDC (0.917 g, 4.79 mmol). The reaction was stirred at room temperature over- night. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with 1 N HC1, sat. NAHC03, brine, dried (Na2SO), and filtered. Evaporation of the solvent gave the title compound (0.600 g, 100%) as a white solid, which was used in the next step without further purification. 1H NMR (CDC13, 400 MHz) 5 7.24 (dd, J=8.6 Hz, J=5.5 Hz, 1H), 7.14 (dd, J=8.6 Hz, J=8.2 Hz, 1H), 3.47 (s, 3H), 3.38 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 15 If the procedure is as described in Example 13, except that 50.1 g (0.175 mol) of 2,3-dichloro-4,4'-difluorobenzophenone and 10 g of 90 percent hydrogen peroxide, solution are used, 11.8 g (0.105 mol, 60%) of 4-fluorophenol and 28.3 g (0.136 mol, 78%) of 2,3-dichloro-4-fluorobenzoic acid are obtained. |
Tags: 154257-76-8 synthesis path| 154257-76-8 SDS| 154257-76-8 COA| 154257-76-8 purity| 154257-76-8 application| 154257-76-8 NMR| 154257-76-8 COA| 154257-76-8 structure
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