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CAS No. : | 1010085-13-8 | MDL No. : | MFCD22124479 |
Formula : | C22H21ClFN3O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LCVIRAZGMYMNNT-UHFFFAOYSA-N |
M.W : | 461.94 | Pubchem ID : | 24748204 |
Synonyms : |
VX-689
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 17 |
Fraction Csp3 : | 0.32 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 118.45 |
TPSA : | 112.58 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.28 cm/s |
Log Po/w (iLOGP) : | 2.86 |
Log Po/w (XLOGP3) : | 5.41 |
Log Po/w (WLOGP) : | 6.13 |
Log Po/w (MLOGP) : | 3.14 |
Log Po/w (SILICOS-IT) : | 5.41 |
Consensus Log Po/w : | 4.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -6.06 |
Solubility : | 0.000406 mg/ml ; 0.000000879 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -7.53 |
Solubility : | 0.0000137 mg/ml ; 0.0000000296 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.71 |
Solubility : | 0.00000901 mg/ml ; 0.0000000195 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.01 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
In ethanol; water at 20℃; for 12 - 96h; | 2.A; 2.B Synthesis of trans-4-(3-chloro-2-fluorophenoxy)-1-(6-(1,3-thiazol-2-ylamino)pyridin-2-yl)methyl)cyclohexanecarboxylic acid EExample 2Synthesis of trans-4-(3-chloro-2-fluorophenoxy)-1-(6-(1,3-thiazol-2-ylamino)pyridin-2-yl)methyl)cyclohexanecarboxylic acid[Method A]To a 47.9 mg of trans-4-(3-chloro-2-fluorophenoxy)-1-(6-(1,3-thiazol-2-ylamino)pyridin-2-yl)methyl)cyclohexanecarboxylic acid hydrochloride as obtained in Example 1 were successively added 4 ml of water and 4 ml of ethanol, followed by stirring the reaction mixture at room temperature for 12 hours. The resulting precipitate was collected by filtration and washed with water to give the title compound as a colorless needle (mp: 202-222 C.).1H-NMR(DMSO-d6)?:1.60-1.92(8H,m), 2.98(2H,s), 4.61 (1H,brs), 6.71 (1H,d,J=7.2 Hz), 6.90(1H,d,J=8.2 Hz), 6.98(1H,d,J=3.5 Hz), 7.10-7.22(3H,m), 7.38(1H,d,J=3.5 Hz), 7.60(1H,t,J=7.6 Hz).mass:462,464(M+1)+[Method B]To 460 mg of trans-4-(3-chloro-2-fluorophenoxy)-1-(6-(1,3-thiazol-2-ylamino)pyridin-2-yl)methyl)cyclohexanecarboxylic acid hydrochloride as obtained in Example 1 were successively added 40 ml of water and 40 ml of ethanol, followed by stirring the reaction mixture at room temperature for 4 days. The resulting precipitate was collected by filtration and washed with water to give the title compound as a colorless plate (mp: 224-242 C.).1H-NMR(DMSO-d6)?:1.60-1.92(8H,m), 2.98(2H,s), 4.61 (1H,brs), 6.71 (1H,d,J=7.2 Hz), 6.90(1H,d,J=8.2 Hz), 6.98(1H,d,J=3.5 Hz), 7.10-7.22(3H,m), 7.38(1H,d,J=3.5 Hz), 7.60(1H,t,J=7.6 Hz).mass:462,464(M+1)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice; Inert atmosphere; | 2.2.4 (2.4) Preparation of TED molecule 4 Weigh compound UBI-1001 (20mg, 0.043mmol) was dissolved in DMF (2mL), was added under ice-water bath successively NH22-Linker-B2 (1 eq.), HOBT (2eq.23mg, 0.086 mmol), EDCI (2eq. 16.4 mg, 0.086 mmol) and TEA (3eq. 13 mg, 0.129 mmol).After the addition was completed, the material system was stirred at room temperature for 18 hours under nitrogen protection. After the reaction was completed, the reaction solution was poured into 5 mL of water and extracted three times with ethyl acetate (5 mL * 3). The organic phases were combined and washed with saturated brine, anhydrous Na2SO4 wasdried, concentrated by rotary evaporation under reduced pressure, and the crude product was obtained. The polar compound (DCM / MeOH = 10/1) was used for thin layer chromatography silica gel plate separation to prepare the target compound TED. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice; Inert atmosphere; | 2.2.3 (2.3) Preparation of TED molecule 3 Weigh the compound UBI-1001 (20mg, 0.043mmol) dissolved in DMF (2mL), add NH2-Linker (L1) -B1 (1eq.), HOBT (2eq. 23mg, 0.086mmol), EDCIin ice water bath(2eq. 16.4 mg, 0.086 mmol) and TEA (3eq. 13 mg, 0.129 mmol).After the addition was completed, the material system was stirred at room temperature for 18 hours under nitrogen protection. After the reaction was completed, the reaction solution was poured into 5 mL of water and extracted three times with ethyl acetate (5 mL * 3). The organic phases were combined and washed with saturated brine, anhydrous Na2SO4 wasdried, concentrated by rotary evaporation under reduced pressure, and the crude product was obtained. The target compound TED was prepared by thin-layer chromatography on a silica gel plate with the polarity of the developing agent (DCM / MeOH = 10/1). |