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CAS No. : | 1313363-54-0 | MDL No. : | MFCD28144684 |
Formula : | C38H47ClN4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CLRSLRWKONPSRQ-CPOWQTMSSA-N |
M.W : | 659.26 | Pubchem ID : | 53240420 |
Synonyms : |
CGM097
|
Num. heavy atoms : | 47 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.47 |
Num. rotatable bonds : | 9 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 199.9 |
TPSA : | 65.56 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.71 cm/s |
Log Po/w (iLOGP) : | 5.89 |
Log Po/w (XLOGP3) : | 6.5 |
Log Po/w (WLOGP) : | 5.12 |
Log Po/w (MLOGP) : | 3.98 |
Log Po/w (SILICOS-IT) : | 5.6 |
Consensus Log Po/w : | 5.42 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -7.71 |
Solubility : | 0.0000128 mg/ml ; 0.0000000194 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -7.67 |
Solubility : | 0.000014 mg/ml ; 0.0000000212 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.57 |
Solubility : | 0.000000177 mg/ml ; 0.0000000003 mol/l |
Class : | Poorly soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 5.79 |
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 |
---|---|---|
23.8% | A sealable reaction flask was charged with potassium phosphate (4.44 g, 20.29 mmol), evacuated and heated for 15 min at 170 C. The reaction flask was back-filled with argon at RT and Intermediate 75.6 (3.64 g, 10.15 mmol), Intermediate 106.1 (5.48 g, 12.18 mmol), dioxan (75 mL) and (+/-)-trans-1,2-diaminocyclohexane (0.37 mL, 3.04 mmol) were added subsequently. The reaction flask was carefully evacuated under vacuum (2×) and backfilled with argon (2×) and copper (I) iodide (0.586 g, 3.04 mmol) were added. The reaction mixture was stirred for 22.5 h at 95 C. The mixture was extracted between EtOAc (3×) and water (3×). The organic phases were washed with brine and dried over Na2SO4, filtered and evaporated to dryness. Purification of the residue by normal phase column chromatography, eluting with 100% EtOAc to 20% MeOH/EtOAc followed by reverse phase prep-HPLC afforded the TFA salt which was extracted between EtOAc (2×) and 1M aqueous NaHCO3 (1×). The organic phases were washed with brine and dried over Na2SO4, filtered and evaporated to dryness gave the title compound as white solid (1.59 g, 2.41 mmol, 23.8%): HPLC: EtRet=4.57 min; LC-MS: m/z 659.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) 0.88-1.01 (m, 2H) 1.05-1.14 (m, 2 H) 1.16 (d, J=5.86 Hz, 3H) 1.21 (d, J=6.25 Hz, 3H) 1.48-1.62 (m, 1H) 1.73 (dd, 4H) 2.14-2.27 (m, 1H) 2.65 (t, J=5.47 Hz, 2H) 2.76 (s, 3H) 2.85 (s, 3H) 3.02 (s, 2H) 3.06-3.20 (m, 4H) 3.54 (d, 1H) 3.71 (s, 3H) 3.87 (d, J=19.53 Hz, 1H) 4.39-4.47 (m, 1H) 5.92 (s, 1H) 6.54 (d, 2H) 6.81 (s, 1H) 6.87 (d, 2H) 7.02 (s, 1H) 7.33 (s, 4H). | |
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 95℃; for 22.5h; | Purification of the residue by normal phase column chromatography, eluting with 100% EtOAc to 20% MeOH/EtOAc followed by reverse phase prep-HPLC afforded the TFA salt which was extracted between EtOAc (2*) and 1M aqueous NaHCO3 (1*). The organic phases were washed with brine and dried over Na2SO4, filtered and evaporated to dryness gave the title compound as white solid (1.59 g, 2.41 mmol, 23.8%): HPLC: EtRet=4.57 min; LC-MS: m/z 659.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) 0.88-1.01 (m, 2H) 1.05-1.14 (m, 2H) 1.16 (d, J=5.86 Hz, 3H) 1.21 (d, J=6.25 Hz, 3H) 1.48-1.62 (m, 1H) 1.73 (dd, 4H) 2.14-2.27 (m, 1H) 2.65 (t, J=5.47 Hz, 2H) 2.76 (s, 3H) 2.85 (s, 3H) 3.02 (s, 2H) 3.06-3.20 (m, 4H) 3.54 (d, 1H) 3.71 (s, 3H) 3.87 (d, J=19.53 Hz, 1H) 4.39-4.47 (m, 1 H) 5.92 (s, 1H) 6.54 (d, 2H) 6.81 (s, 1H) 6.87 (d, 2H) 7.02 (s, 1H) 7.33 (s, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | 500 mL of reaction flask was added compound 27 (26 g, 33 mmol)And hydrochloric acid / dioxane (5N, 33 mL),The reaction was stirred at room temperature for 3 hours. After the reaction solution was concentrated, Dissolved in methanol (200 mL), reduced to 0 C,Triethylamine (46 mL, 330 mmol) was added dropwise and the reaction was carried out overnight at room temperature.The reaction solution was concentrated, dissolved in methylene chloride, Washed with sodium bicarbonate solution (1 M), the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated,The resulting crude column chromatography (petroleum ether: ethyl acetate: acetone = 1: 1: 0.3-0: 1: 0.6)To give yellow solid compound I-1 (13 g, yield 59%). |