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CAS No. : | 747413-18-9 | MDL No. : | |
Formula : | C17H27BN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DCWPPXDQCNZIEI-UHFFFAOYSA-N |
M.W : | 302.22 | Pubchem ID : | 59264746 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.65 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 99.18 |
TPSA : | 24.94 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.13 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.84 |
Log Po/w (WLOGP) : | 0.98 |
Log Po/w (MLOGP) : | 1.57 |
Log Po/w (SILICOS-IT) : | 1.42 |
Consensus Log Po/w : | 1.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.57 |
Solubility : | 0.0808 mg/ml ; 0.000267 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.02 |
Solubility : | 0.287 mg/ml ; 0.000951 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.15 |
Solubility : | 0.0212 mg/ml ; 0.0000701 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.22 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-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 |
---|---|---|
With triethylamine In dichloromethane; toluene at 100℃; for 1h; Irradiation; | 31.3 To a solution of PDCI2 (dppf). DCM (10MG, 0.012 MMOL) in anhydrous toluene (4ml) in an argon filled sealed microwave tube was added the 1- (3-BROMO- PHENYL)-4-METHYL-PIPERAZINE (100MG, 0. 39MMOL), Et3N (0. 11ML, 2 equiv. ), and 4,4, 5, 5-TETRAMETHYL-1, 3, 2-DIOXABOROLANE (0. 09MOI, 1.5 equiv). The microwave tube was evacuated and backfilled with Argon before being irradiated in a CEM Microwave reactor at 100 C for 1 HR using an initial power of 200W. The reaction mixture was partitioned between more toluene (6ml) and water (10MUT), the organic layer separated, washed with water (1 x 10MUT), dried over MGS04 and then evaporated IN VACUO to leave a purple/brown residue which was used for suzuki coupling without further purification. LCMS TR = 0.97, MS m/z 303.5 [M+H] + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.6% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dichloromethane at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
198 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 3h; | 2 Synthesis of 1-methyl-4-[3-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-phenyl]- piperazine To 1-(3-bromo-phenyl)-4-rnethyl-piperazine (0.7 g, 2.73 mmol) in 1,4 dioxane (100 ml) is added bis(pinacolato)diboron (1.04 g, 4.09 mmol), KOAc (0.80 g, 8.19 mmol) and Pd(dppf)CI2 (111 mg, 0.14 mmol). The mixture is heated to 90°C for 3 h, quenched with water (100 ml), followed by extraction with EtOAc. The organic layer is separated, washed with brine and dried over Na2S04. The drying agent is filtered and the solvent is removed in vacuum. The product is isolated by chromatography (DCM/EtOH); yield: 198 mg 1-methyl-4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan- 2-yl)-phenyl]-piperazine; HPLC/MS: 1.48 min, [M+H] = 303. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; | 79.1 Step 1. 1-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine Sodium triacetoxyborohydride (0.066 g, 0.31 mmol) was added to a solution of 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (60.0 mg, 0.208 mmol, from Boron Molecular) and 11.0 M aqueous formaldehyde (0.057 mL, 0.62 mmol) in methylene chloride (0.8 mL, 10 mmol) and then the reaction was stirred at r.t. for 1 hour. The mixture was diluted with methylene chloride, washed with saturated NaHCO3, water, brine, then dried over Na2SO4, filtered and concentrated to provide the product which was used in the next step. LCMS calculated for C17H28BN2O2 (M+H)+: m/z=303.2. Found 303.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube; | 67.b b) (2-(4-Methyl-1 ,4-diazepan-1-yl)pyridin-4-yl)boronic acid General procedure: A Shlenk tube was charged with 1 -(4-bromopyridin-2-yl)-4-methyl-1 ,4-diazepane (Preparation 33a, 0.67 g, 2.48 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1 ,3,2- dioxaborolane (0.76 g, 2.98 mmol), potassium acetate (0.73 g, 7.44 mmol) and 1 ,4- dioxane (8 ml_). The Schlenk tube was subjected to three cycles of evacuation- backfilling with argon and then [1 ,1 -bis (diphenylphosphino)ferrocene]palladium(ll) dichloride (0.10 g, 0.12 mmol) was added. After three further cycles of evacuation- backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated at 80 °C for 4h. The mixture was cooled, filtered through diatomaceous earth (Celite) and the solvent was concentrated to dryness. The residue was treated with petroleum ether, filtered and the solvent was evaporated to dryness to yield the title compound (0.5 g, 86%) as a yellow oil. |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 16h; | 246 General procedure: A mixture of Compound 27B (1.35 g, 5.4mmol), Pd(dppf)C12 (0.35 g, 0.43 mmol), 4,4,4,4,5,5,5’, 5’-octamethyl-2,2’-bi( 1,3 ,2-dioxaborolane) (2.09 g, 8.22 mmol), and potassium acetate (1.62 g, 16.5 mmol) in 1,4-dioxane (50 ml) was heated at 80°C for 16 hours. The mixture was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to furnish Compound 27C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. | |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 16h; | 246 General procedure: A mixture of Compound 27B (1.35 g, 5.4mmol), Pd(dppf)Cl2 (0.35 g, 0.43 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (2.09 g, 8.22 mmol), and potassium acetate (1.62 g, 16.5 mmol) in 1,4-dioxane (50 ml) was heated at 80 o C for 16 hours. The mixture was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to furnish Compound 27C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.5% | With sodium carbonate In 1,4-dioxane; water | 7.2 2, N- hydroxy-1 - ((3 '- (4-methyl-piperazin-1-yl) - [1,1'-biphenyl] -4-yl) sulfonyl) -2,5- hydrogen -1H- pyrrole-3- (tetrahydropyran-2-yloxy) - carboxamide 1 - ((4-bromophenyl) sulfonyl) -1H- pyrrole-2,5-dihydro-3- (tetrahydropyran-2-yloxy) - carboxamide (431mg, 1.0mmol) was dissolved in 10mL 2mL of dioxane and water, and then added sodium carbonate (212mg, 2mmol,) and 1 - ((3 '- (4-methyl-piperazin-1-yl) - phenyl boronic acid pinacol ester (302 mg of the, 1.0mmol, manufacturer: J & K Technology Co., Ltd.), was added [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (50mg) and the solution was purged with nitrogen three times and heated to 80. for 2 hours. after completion of the reaction the reaction solution out of the organic solvent in vacuo, diluted with 20mL of water was added, and extracted three times with dichloromethane, the combined organic phase was dried and concentrated in vacuo to give the crude product, the crude product was purified by chromatography to give a white solid after N - hydroxy - 1 - ((3 '- (4-methyl-piperazin-1-yl) - [1,1'-biphenyl] -4-yl) sulfonyl) -2,5-dihydro -1H - pyrrolidin-3- (tetrahydropyran-2-yloxy) - carboxamide (250.00mg, 47.5% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-methyl-4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]piperazine; C17H25BrN4O With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 1h; Inert atmosphere; Microwave irradiation; Stage #2: trifluoroacetic acid |
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