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CAS No. : | 261762-97-4 | MDL No. : | MFCD01631439 |
Formula : | C8H6ClFO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NOKLOLLCDCEFAK-UHFFFAOYSA-N |
M.W : | 188.58 | Pubchem ID : | 2773723 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.95 |
TPSA : | 37.3 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) : | -5.82 cm/s |
Log Po/w (iLOGP) : | 1.63 |
Log Po/w (XLOGP3) : | 2.3 |
Log Po/w (WLOGP) : | 2.53 |
Log Po/w (MLOGP) : | 2.67 |
Log Po/w (SILICOS-IT) : | 2.61 |
Consensus Log Po/w : | 2.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.7 |
Solubility : | 0.38 mg/ml ; 0.00201 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.72 |
Solubility : | 0.358 mg/ml ; 0.0019 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.07 |
Solubility : | 0.159 mg/ml ; 0.000845 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.5 |
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 |
---|---|---|
Example 193; 2-{3-[2-(5-Chloro-2-fluoro-phenyl)-ethoxy]-4-methoxy-benzoylamino}-indane-2- carboxylic acid; Step 1 : 2-(5-Chloro-2-fluoro-phenyl)-ethanol; A solution of 5 g (26.51 mmol) of delta-chloro^-fluoro-phenylacetic acid in 60 ml of THF was added dropped to a suspension of 2.012 g (53.02 mmol) of lithium aluminium hydride in 26.5 ml of THF. 30 ml of THF were added, and the mixture was heated under reflux for 3 h. After cooling to 0 0C, a solution of 929.7 mg (16.57 mmol) of potassium hydroxide in 4 ml of water was cautiously added and the mixture was stirred overnight at room temperature. The formed precipitate was filtered off with suction and washed with THF. The combined filtrates were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (DCM/methanol 98:2) to give 3.8 g of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 72.0h; | [0459] A vial with stir bar was charged with 2-(3-phenylIH-pyrazol-1-yl)acetic acid (0.072 g, 0.356 mmol), ExampleIG (0.109 g, 0.293 mmol), EDC (0.074 g, 0.3S6 mmol) andHOBT (0.050 g, 0.327 mmol) in dichloromethane (4 mL).N-methylmorpholine (0.1 mL, 0.910 mmol) was added, andthe mixture was stirred at ambient temperature for 72 hours.The mixture was shaken in a seperatory funnel with 30 mLeach of dichloromethane and aqueous sodium carbonate. Theorganics were dried over sodium sulfate, filtered and concentrated.The crude material was purified by HPLC (CIS,CH3CN/water (0.1% TFA), 0-100%) to provide the trifluoroacetate salt of the title compound. 1 H NMR ( 400 MHz,DMSO-d6) o10.42 (s, lH), 7.80 (m, 3H), 7.63-7.55 (m, 2H),7.52 (dd, 1=8.9, 2.6 Hz, lH), 7.45-7.34 (m, 3H), 7.29 (t, 1=7.4Hz, lH), 7.01 (t, 1=7.2 Hz, 2H), 6.90 (d, 1=8.7 Hz, lH), 6.75(d, 1=2.2 Hz, lH), 5.79 (s, lH), 5.06 (s, 2H), 3.89 (dd, 1=15.2,8.1 Hz, 2H), 3.34 (s, 3H), 1.13 (t, 1=6.9 Hz, 3H). MS (ESI)m/z 557.1 (M+W). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 50℃; for 16.0h; | 5-Am ino-2-(1 -cyclopropyl-1 H-pyrazol-4-yl)-N-[(d imethylam ino)methylidene]benzenesulfonamide (200 mg, 600 pmol) was dissolved in DMF (10 ml) and (5-chloro-2- fluorophenyl)acetic acid (136 mg, 720 pmol) was added followed by the addition of N,Ndiisopropylethylamine (520 p1, 3.0 mmol) and HATU (456 mg, 1.20 mmol). The reaction was stirred at 50C for 16h. Water and ethyl acetate were added. The phases wereseparated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Whatmanfilter and the solvent was removed under reduced pressure. The crude was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25℃; for 2.0h; | General procedure: Compound 1-7 (110.86 mg, 399.73 mmol), compound 1-10 (0.2 g, 799.45 mmol) and diisopropylethylamine(154.98 mg, 1.20 mmol) were added to DMF (2mL), and then T3P (713.19 mL, 1.20 mmol, 50% purity) was added,the reaction mixture was stirred at 25 C for 2 hours. After the completion of the reaction, the mixture was extractedwith ethyl acetate (50mL 3) and water (50mL). The organic phase was dried over anhydrous sodium sulfate,concentrated and separated by preparative TLC (dichloromethane: methanol = 20: 1), and then resolved by chiralHPLC (chromatographic column: AD (250mm 30mm, 10mm); mobile phase: [0.1% NH3H2O IPA]; B%: 35% -35%)to give compound 1 or 2. MS ESI calculated C21H22 F3N7O3S [M + H]+ 510, found 510. Isomer 1 (Example 1) hada retention time of 5.87 minutes; 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.50 - 1.64 (m, 2 H), 2.18 (br d, J=10.04Hz, 2 H), 3.17 - 3.29 (m, 2 H), 3.49 (s, 3 H), 3.88 - 3.93 (m, 1 H), 4.33 (br d, J=13.55 Hz, 2 H), 5.01 (s, 1 H), 7.28 -7.33 (m, 2 H), 7.38 - 7.46 (m, 2 H), 7.49 - 7.55 (m, 2 H), 8.47 (d, J=3.51 Hz, 1 H).Isomer 2 (Example 2) had a retention time of 6.30 minutes; 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.51 -1.63 (m, 2 H), 2.18 (br d, J=10.04 Hz, 2 H), 3.18 - 3.27 (m, 2 H), 3.49 (s, 3 H), 3.88 - 3.93 (m, 1 H), 4.33 (br d, J=13.55Hz, 2 H), 5.01 (s, 1 H), 7.27 - 7.33 (m, 2 H), 7.38 - 7.46 (m, 2 H), 7.48 - 7.55 (m, 2 H), 8.47 (d, J=3.51 Hz, 1 H). |
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