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CAS No. : | 710348-69-9 | MDL No. : | MFCD09260491 |
Formula : | C13H17BN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LQVSXEXWXILGBH-UHFFFAOYSA-N |
M.W : | 260.10 | Pubchem ID : | 43811065 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.46 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 75.4 |
TPSA : | 67.11 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.79 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.55 |
Log Po/w (WLOGP) : | 1.16 |
Log Po/w (MLOGP) : | 0.95 |
Log Po/w (SILICOS-IT) : | 2.01 |
Consensus Log Po/w : | 1.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.71 |
Solubility : | 0.503 mg/ml ; 0.00193 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.57 |
Solubility : | 0.702 mg/ml ; 0.0027 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.42 |
Solubility : | 0.00987 mg/ml ; 0.0000379 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.9 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
44% | With potassium acetate In DMF (N,N-dimethyl-formamide) at 95℃; | 5-BROMO-1, 3-dihydro-benzoimidazol-2-one (20.0 g, 93.9 mmol) is dissolved in argon purged anhydrous DMF (150 mL). To this solution is added bis (pinacolato) diboron (28.6 g, 113 mmol), KOAC (27.6 g, 282 mmol), and PDCL2 (DPPF), 1: 1 complex with CH2C12 (7.67 g, 9.40 mmol). The reaction is heated to 95 °C overnight with mechanical stirring then cooled to room temperature and diluted with brine (500 mL) and EtOAc (750 mL). The mixture is filtered to remove a dark brown solid, which is washed thoroughly with EtOAc. The layers are separated and the organics washed with water (3 x 500 mL), then dried (MGS04), filtered and evaporated under reduced pressure. Trituration with 1: 1 CH2CL2/HEXANES affords the product (10.9 g, 44percent). RF 0. 52 (silica gel, 85: 15 CH2C4LMEOH) ; mp 313-315 °C (dec) ;APOS;H NMR (300 MHz, DMSO-d6) 21. 27 (s, 12 H), 6.92 (d, J= 7.7 Hz, 1H), 7.17 (s, 1H), 7.28 (d, J= 7.7 Hz, 1H), 10.62 (s, 1H), 10.74 (s, 1H) ; APCI MS m/z 261 [CL3HL7BN203 + H] + ; HPLC = 98.3percent, TR= 18. 3 min; Analysis for C13HL7BN203 : C, 57.07 ; H, 6.82 ; N, 10.24. Found: C, 56.69 ; H, 6.44 ; N, 10.21. HPLC conditions: Waters Symmetry C18 column (4.6 mm x 250 mm); 95: 5 to 0: 100 WATER/MECN ; 1.0 mL/min (25 min), D = 254 nm |
41% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 95℃; for 16 h; Inert atmosphere | To a round-bottomed flask containing DMF (35 mL) was added 5-bromo-1 ,3—dihydro- benzimidazo-2one (5.Og, 23 mmo), and the resu[ting soution was purged with nitrogen for 15 minutes. To this soution were added successivey bis(pinacoato)diboron (7.2g, 28mmo), potassium acetate (6.9g, 70 mmo), and PdC2(dppf)0H2C2 (1 .7g, 2.4 mmd). After heating at 95 °C for 16 h, the back mixture was coded to rt and di’uted with brine (50 mL) and EtOAc (75 mL). The resu[ting precipitate was removed by fiftration and washed with EtOAc. The fiftrate was transferred to a separatory funnd and the ayers separated. The organic ayer was washed with water (3 x 50 mL), dried (Na2SO4), fiftered andconcentrated in vacuo. Trituration of the crude residue with DOM provided the desired product as a white soid (2.5g, 41 percent yied). MS (ES): masss cacd. for 013H17BN203, 260.1; m/zfound, 261.2 [M+H1. 1H NMR (400 MHz, DMSO.-d6) 310.76 (s, IH), 10.65 (s, IH), 7.29 (dd, J= 7,7, 1.0 Hz, IH), 7.18 (s, IH), 6.92 (d, J= 7.5 Hz, IH), 127 (5, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.2% | at 23℃; for 16 h; | Step B: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol- 2-one. To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine (17 mmol) in EtOAc (360 mL) was added 1,1'-carbonyldiimidazole (CDI) (3.0 g, 19 mmol). The resulting mixture was stirred at 23 °C for 16 h. The reaction mixture was diluted with DCM and the resulting white solid was filtered and washed with MeOH to afford the title compound (10.8 g, 63.2percent). |
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