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CAS No. : | 1783418-59-6 | MDL No. : | MFCD28246532 |
Formula : | C5H9ClF3N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CHXOWBWATJMPOW-UHFFFAOYSA-N |
M.W : | 175.58 | Pubchem ID : | 84717721 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 33.64 |
TPSA : | 26.02 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) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.8 |
Log Po/w (WLOGP) : | 3.29 |
Log Po/w (MLOGP) : | 1.66 |
Log Po/w (SILICOS-IT) : | 1.71 |
Consensus Log Po/w : | 1.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.93 |
Solubility : | 2.06 mg/ml ; 0.0117 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.97 |
Solubility : | 1.9 mg/ml ; 0.0108 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.6 |
Solubility : | 4.38 mg/ml ; 0.0249 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.06 |
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 |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 72h; Inert atmosphere; | 29.1 Step 1 : 3,4-Diamino-N-[[1-(trifluoromethyl)cyclopropyl]methyl]benzamide A solution of 3,4-diaminobenzoic acid (150 mg, 0.99 mmol), [1- (trifluoromethyl)cyclopropyl]methanamine hydrochloride (173 mg, 0.99 mmol), EDCI (208 mg, 1.08 mmol) and DMAP (132 mg, 1.08 mmol) in DCM (10 ml_) was stirred at room temperature. DIPEA (344 mI_, 1.97 mmol) was added and the reaction mixture was stirred under an inert atmosphere for 3 days. The resulting mixture was diluted with DCM (20 ml_), washed with water (2 x 20 ml_), dried over Na2SC>4 and concentrated in vacuo. Purification of the crude material by chromatography on silica eluting with 0-100% MeOH in EtOAc afforded the title compound as a tan residue. 1 H NMR (500 MHz, DMSO-d6) d 7.96 (t, J = 6.2 Hz, 1 H), 7.02 (d, J = 2.0 Hz, 1 H), 6.95 (dd, J = 8.1 , 2.0 Hz, 1 H), 6.48 (d, J = 8.1 Hz, 1 H), 4.96 (s, 2H), 4.55 (s, 2H), 3.54 (d, J = 6.2 Hz, 2H), 0.92 - 0.81 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With [(2-di-tert-butylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2’-amino-1,1‘-biphenyl)] palladium(II) methanesulfonate; sodium tertiary butoxide In tert-Amyl alcohol at 110℃; for 12h; Inert atmosphere; | 1 Step 1: tert-Butyl 3-[5-[[1-(trifluoromethyl)cyclopropyl]methylamino]-2-pyridyl]azetidine-1- carboxylate To a solution of tert-butyl 3-(5-bromo-2-pyridyl)azetidine-1-carboxylate (1.0 g, 3.19 mmol, 1.0 equiv; CAS RN 1922143-52-9) and [1-(trifluoromethyl)cyclopropyl]methanamine; hydrochloride (0.56 g, 3.19 mmol, 1.0 equiv; CAS RN 1783418-59-6) in tert-amyl alcohol (10 mL) under Ar was added tBuXPhos Pd G3 (0.25 g, 0.32 mmol, 0.10 equiv; CAS RN 1447963- 75-8) and sodium tert-butoxide (1.23 g, 12.77 mmol, 4.0 equiv) and the reaction mixture was heated at 110 °C for 12 h. The reaction mixture was filtered, and the crude material purified by preparative HPLC (Phenomenex Gemini 5 mm C18110 A Axia column (75 mm x 30 mm, 5 mm); 0.1 % v/v FA in water and MeCN) to give the title compound as a yellow solid (380 mg, 32 %). MS (ESI): m/z = 316.2 [M+2H-tBu]+. |
32% | With [(2-di-tert-butylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2’-amino-1,1‘-biphenyl)] palladium(II) methanesulfonate; sodium tertiary butoxide In tert-Amyl alcohol at 110℃; for 12h; Inert atmosphere; | 1 Step 1: tert-Butyl 3-[5-[[1-(trifluoromethyl)cyclopropyl]methylamino]-2-pyridyl]azetidine-1- carboxylate To a solution of tert-butyl 3-(5-bromo-2-pyridyl)azetidine-1-carboxylate (1.0 g, 3.19 mmol, 1.0 equiv; CAS RN 1922143-52-9) and [1-(trifluoromethyl)cyclopropyl]methanamine; hydrochloride (0.56 g, 3.19 mmol, 1.0 equiv; CAS RN 1783418-59-6) in tert-amyl alcohol (10 mL) under Ar was added tBuXPhos Pd G3 (0.25 g, 0.32 mmol, 0.10 equiv; CAS RN 1447963- 75-8) and sodium tert-butoxide (1.23 g, 12.77 mmol, 4.0 equiv) and the reaction mixture was heated at 110 °C for 12 h. The reaction mixture was filtered, and the crude material purified by preparative HPLC (Phenomenex Gemini 5 mm C18110 A Axia column (75 mm x 30 mm, 5 mm); 0.1 % v/v FA in water and MeCN) to give the title compound as a yellow solid (380 mg, 32 %). MS (ESI): m/z = 316.2 [M+2H-tBu]+. |