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CAS No. : | 890839-31-3 | MDL No. : | MFCD12546621 |
Formula : | C13H16BClO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MFHUTQFPFZUQCI-UHFFFAOYSA-N |
M.W : | 282.53 | Pubchem ID : | 46739773 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.46 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 74.89 |
TPSA : | 55.76 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.85 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.06 |
Log Po/w (WLOGP) : | 2.34 |
Log Po/w (MLOGP) : | 1.81 |
Log Po/w (SILICOS-IT) : | 1.9 |
Consensus Log Po/w : | 1.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -3.62 |
Solubility : | 0.0676 mg/ml ; 0.000239 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.9 |
Solubility : | 0.0358 mg/ml ; 0.000127 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.98 |
Solubility : | 0.0294 mg/ml ; 0.000104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.79 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
69% | With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; dichloromethane; at 80℃; for 5h; | Preparation 11. 2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoic acid; To a solution of <strong>[59748-90-2]4-bromo-2-chlorobenzoic acid</strong> (0.15 g, 0.64 mmol) and bis(pinacolato)diboron (0.19 g, 0.76 mmol) in dioxane (30 mL) was added [1 ,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane (0.015 g, 0.019 mmol) and potassium acetate (0.18 g, 1.92 mmol). The reaction mixture was stirred at 80 0C for 5 h. After cooling to room temperature, ethyl acetate (10 mL) and water (10 mL) were added. The aqueous layer was extracted with ethyl acetate (2 x 20 mL). The organic portions were concentrated and recrystallized with hot hexanes to give the pure product (0.13 g, 69percent). MS(ES) m/e 283 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80.0℃; for 16.0h;Inert atmosphere; | N-(5-bromopyridin-3-yl)cyclopropanesulfonamide (0.810 g, 2.92 mmol), sodium carbonate (1.24 g, 11.69 mmol) and 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)benzoic acid (0.991 g, 3.51 mmol) were combined in 1,4-dioxane (32 mL) and water (6.4 mL) followed by tetrakis(triphenylphosphine)palladium (0) (0.34 g, 0.292 mmol) to give a light yellow suspension. The suspension was placed under nitrogen and heated for 16 h at 80 C. The reaction was filtered through Celite and the solids washed with 1,4- dioxane followed by ethyl acetate. Concentrating the solvents obtained a pale yellow sticky solid. This was suspended in 50 mL of water and basified with 1 N NaOH solution until the pH was 12. The basic layer was washed once with 25 mL of ethyl acetate. After a back-extraction of the organic phase with 20 mL of water at pH=12, the combined basic phases were acidified with 1 N HC1 until pH=5 was reached. After standing overnight the precipitate was collected and dried to afford 2-chloro-4-(5-(cyclopropanesulfon- amido)pyridin-3-yl)benzoic acid (0.438 g, 1.24 mmol, 35%) as an off-white solid. MS (ESI, pos. ion) m/z: 353, 355 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 40.0℃; for 6.0h; | Step A.(R)-N-(1 -(3-Amino-4-chloroisoxazolo[5 ,4-clpyridin-7-yl)pyrrolidin-3-yl)-2-chloro-4-(4,4,5 ,5-tet ramethyl- 1,3 ,2-dioxaborolan-2-yl)benzamideTo a solution of (R)-7-(3 -aminopyrrolidin- 1 -yl)-4-chloroisoxazolo [5 ,4-c]pyridin-3 -aminedihydrochloride (0.92 mmol, 300 mg, EXAMPLE 11, Step E) and2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoic acid (1.0 mmol, 285 mg) in CH2C12 (6.0 mL) was added HATU (1.4 mmol, 524 mg) and DIPEA (2.8 mmol, 0.48 mL). The reaction mixture was stirred at 40 C for 6 h. Then the mixture was diluted with MeOH. The crude mixture was purified by 5i02 column chromatography (heptane:EtOAc = 50:50 to 0:100)to give the title compound.‘H NMR (400 MHz, DMSO-d6) 5 (ppm): 8.83 (1H, d, J= 6.4 Hz), 7.78 (1H, s), 7.62-7.59 (2H, m), 7.44 (1H, d, J= 7.3 Hz), 6.21 (2H, s), 4.58-4.50 (1H, m), 3.99-3.93 (1H, m), 3.87-3.74 (3H, m), 2.28-2.18 (1H, m), 2.09-2.00 (1H, m), 1.29 (12H, s)MS (ESI) mlz = 518, 520 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90.0℃; for 2.0h; | Step A. 2-Chloro-4-(pyridazin-4-yl)benzoic acidThe mixture of 2-chloro-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzoic acid (2.3 mmol,650 mg), 4-bromopyridazine hydrobromide (2.1 mmol, 500 mg), PdC12(dppf) (0.1 mmol, 76 mg),Cs2CO3 (10 mmol, 3.4 g) in 1,4-dioxane / water (15 mL / 15 mL) was degassed and heated at90 C for 2 h. The reaction mixture was poured into water (50 mL), washed with EtOAc (30 mL).The aqueous layer was adjusted to pH 3 using iN aq. HC1 and then the precipitate was filtered togive the title compound. MS (ESI) mlz = 235, 237 (M+H)‘H NMR (DMSO-d6) 5 (ppm): 9.71 (1H, dd, J= 2.5, 1.1 Hz), 9.34 (1H, dd, J 5.5, 0.9 Hz), 8.14(1H, d, J= 1.4 Hz), 8.11 (1H, dd, J= 5.5, 2.7 Hz), 7.98 (1H, dd, J 8.0, 1.6 Hz), 7.93 (1H, d, J8.2 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90.0℃; for 2.0h; | The mixture of 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid (2.3 mmol, 650 mg), 4-bromopyridazine hydrobromide (2.1 mmol, 500 mg), PdCl2(dppf) (0.1 mmol, 76 mg), Cs2C03 (10 mmol, 3.4 g) in 1,4-dioxane / water (15 mL / 15 mL) was degassed and heated at 90 C for 2 h. The reaction mixture was poured into water (50 mL), washed with EtOAc (30 mL). The aqueous layer was adjusted to pH 3 using IN aq. HC1 and then the precipitate was filtered to give the title compound. MS (ESI) m/z = 235, 237 (M+H) (0919) 1H NMR (DMSO-d6) |
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