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CAS No. : | 869288-64-2 | MDL No. : | MFCD11519967 |
Formula : | C22H20F3N5O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HESLKTSGTIBHJU-UHFFFAOYSA-N |
M.W : | 491.49 | Pubchem ID : | 11612883 |
Synonyms : |
FAK Inhibitor II;Focal Adhesion Kinase Inhibitor II
|
Num. heavy atoms : | 34 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.23 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 123.56 |
TPSA : | 121.46 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.05 cm/s |
Log Po/w (iLOGP) : | 2.3 |
Log Po/w (XLOGP3) : | 3.16 |
Log Po/w (WLOGP) : | 5.46 |
Log Po/w (MLOGP) : | 2.86 |
Log Po/w (SILICOS-IT) : | 3.27 |
Consensus Log Po/w : | 3.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.81 |
Solubility : | 0.00765 mg/ml ; 0.0000156 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.38 |
Solubility : | 0.00204 mg/ml ; 0.00000416 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.99 |
Solubility : | 0.000000497 mg/ml ; 0.000000001 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.33 |
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 |
---|---|---|
54% | With triethylamine In 1-methyl-pyrrolidin-2-one at 100℃; for 1h; | 1 Preparation of 6-[4-(3-Methanesulfonyl-benzylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-3,4-dihydro-1H-quinolin-2-one 6-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3,4-dihydro-1H-quinolin-2-one (50 mg, 0.145 mmol) was added to 0.5 ml NMP and 3-Methanesulfonyl-benzylamine mono hydrochloride salt (32 mg, 0.145 mmoles) and triethylamine (0.060 ml, 0.435 mmoles) were added the reaction was heated to 100° C. for one hour. The reaction was cooled to room temperature and 0.5 mL NMP was added. The reaction was then filtered and purify by preparative reverse phase HPLC 30×50 mm XTerra C18 prep column, fifteen minute gradient 15-60% (0.1% NH4OH in Acetonitrile) and (0.1% NH4OH in water)), flow rate 40 mL/min. The desired product eluted (retention time 8.41 minutes) and was concentrated to a solid (38 mg, 54% yield). 1H NMR (Methanol-d4, 400 MHz) δ 2.52 ( m, 2H), 2.80 (m, 2H), 2.99 (s, 3H), 4.80 (s, 2H), 6.73 (d, J=9 Hz; 1H), 7.22 (d, J=9 Hz; 1H), 7.37 (s, 1H), 7.57 (t, J=8 Hz; 1H), 7.64 (d, J=8 Hz;1H), 7.80 (m, 1H), 7.90 (s, 1H), 8.12 (s, 1H). HPLC ret. time: 5.390, LRMS (M+) 492.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With N-ethyl-N,N-diisopropylamine In butan-1-ol at 100℃; for 16h; | 32 Example 6: Synthesis of N2N4-diaryl-S-itrifluoromethy pyrimidine^^-diamine derivatives (using reaction conditions E and F, Method 4) General procedure: Example 6: Synthesis of N2N4-diaryl-S-itrifluoromethy pyrimidine^^-diamine derivatives (using reaction conditions E and F, Method 4)To a solution of 5-trifluromethyl-2,4-dichloropyrimidine (4.6 mmol, 1 equiv.) inDCEr'BuOH (1 : 1 , 40 mL) was added ZnCl2(5.5 mmol, 1.2 equiv.) at 0 °C. After 1 h, appropriate aniline (1 equiv.) and triethylamine (4.6 mmol, 1.2 equiv) in DCE:lBuOH (4 mL) was added to the reaction mixture. After stirring for 1.5 h, the reaction mixture was concentrated to get the crude product. The crude product was triturated with MeOH, filtered and dried to yield the desired 5-trifluromethyl-4-chloro-N-arylpyrimidin-2-amine derivative (Method 4a). To a solution of 5-trifluromethyl-4-chloro-N-arylpyrimidin-2-amine derivative (1 mmol, 1 equiv) in "BuOH (10 mL), were added appropriate aniline (1 mmol, 1 equiv.) and DIPEA (1 mmol, 1 equiv.). The reaction mixture was stirred at 100 °C for 16 h. It was then cooled to room temperature excess solvent was reduced under reduced pressure. The crude residue was purified using automated prep-HPLC to yield the desired 5-trifluromethyl-N2,N4-diarylpyrimidine-2,4-diamine derivatives (Method 4b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In 1-methyl-pyrrolidin-2-one |