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CAS No. : | 1095708-32-9 | MDL No. : | MFCD12032217 |
Formula : | C16H25BN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SAAGMIHGVLKZBC-UHFFFAOYSA-N |
M.W : | 320.19 | Pubchem ID : | 49760449 |
Synonyms : |
|
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 90.96 |
TPSA : | 69.68 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 : | Yes |
Log Kp (skin permeation) : | -6.31 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.74 |
Log Po/w (WLOGP) : | 2.54 |
Log Po/w (MLOGP) : | 1.21 |
Log Po/w (SILICOS-IT) : | 1.29 |
Consensus Log Po/w : | 1.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.41 |
Solubility : | 0.123 mg/ml ; 0.000385 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.86 |
Solubility : | 0.0444 mg/ml ; 0.000139 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.55 |
Solubility : | 0.00894 mg/ml ; 0.0000279 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.46 |
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 |
---|---|---|
76% | With potassium acetate In dimethyl sulfoxide at 85℃; for 1.25 h; Inert atmosphere | Preparation 24terf-Butyl (4-bromopyhdin-2-yl)carbannate (0.494 g, 1 .81 mmol), bis(pinacolato)diboron (1 .4 g 5.51 mmol ) and potassium acetate (0.535 g , 5.45 mmol) were stirred in dimethylsulfoxide (8 ml_). The mixture was flushed with nitrogen for 10 minutes. [1 ,1 '- Bis(diphenylphosphino)ferrocene] dichloropalladium(ll) (0.150 g, 0.184 mmol) was added and the system flushed for a further 5 minutes with nitrogen before heating the reaction mixture to 85°C under nitrogen for 1 hour. The reaction mixture was diluted in ethyl acetate (15 ml_) and washed with aqueous hydrochloride solution (10 ml_, 0.2 M). Some of the product went into the aqueous layer and some stayed in the organic layer. The aqueous layer was treated with saturated aqueous sodium carbonate carefully until ~pH 6 was achieved then extracted with ethyl acetate (10 ml_). The organics were dried over sodium sulfate, filtered and concentrated in vacuo to give title compound as a white solid (0.44 g, 76percent).1HNMR (de -DMSO): δ 1 .29 (s, 12H), 1 .45 (s, 9H), 7.15-7.17 (d, 1 H), 8.07 (s, 1 H), 8.24- 8.25 (d, 1 H), 9.77 (s, 1 H)LCMS Rt = 0.68 min MS m/z 183.1 [MH]+ |
56% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 5 h; | A solution of intermediate 20b (352 mg), potassium acetate (380 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (360 mg) and Pd(dppf)Cl2.CH2Cl2 (105 mg) in dry DMF (10 mL) was stirred at 80° C. for 5 h. The volatiles were removed under reduced pressure, the residue dissolved in EtOAc and the organic layer was washed with water, dried and the volatiles were removed under reduced pressure. The crude product was purified through washing with heptane to yield the desired compound (56percent yield). LC-MS (Method 1): m/z [M (boronic acid)+H]+=239.2 (MW (boronic acid) calc.=238.05); Rt=2.3 min. |
56% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 5 h; | Intermediate 20c) A solution of intermediate 20b (352 mg), potassium acetate (380 mg), 4,4,4',4', 5,5,5', 5'-octamethyl-2,2'- bi(1 ,3,2-dioxaborolane) (360 mg) and Pd(dppf)CI2-CH2CI2 (105 mg) in dry DMF (10 mL) was stirred at 80 °C for 5 h. The volatiles were removed under reduced pressure, the residue dissolved in EtOAc and the organic layer was washed with water, dried and the volatiles were removed under reduced pressure. The crude product was purified through washing with heptane to yield the desired compound (56percent yield) LC- S (Method 1): m/z [M (boronic acid)+H]+ = 239.2 (MW (boronic acid) calc. = 238.05); R, = 2.3 min. |
53% | With potassium acetate In N,N-dimethyl-formamide at 80℃; for 2 h; Inert atmosphere | Step 6.1. tert-Butyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrid-2-yl]carbamate To a solution of 6.76 (24.8 mmol) of tert-butyl (4-bromopyrid-2-yl)carbamate (Deady, Leslie W.; Korytsky, Olga L.; Rowe, Jeffrey E.; Aust. J. Chem.; 35; 10; 1982; 2025-2034) in 150 mL of dimethylformamide are added 8.0 g (81 mmol) of potassium acetate predried at 130° C. and 6.9 g (27 mmol) of bis(pinacolato)diboron. A stream of argon is then sparged through for a few moments, and 1.2 g (1.5 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) are added. The mixture is stirred at 80° C. under argon for 2 hours and then poured into saturated aqueous ammonium chloride solution. The product is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and the solvent is stripped off under reduced pressure. The residue is triturated in 300 mL of refluxing diisopropyl ether and the insoluble matter is separated out by filtration. The filtrate is cooled and partially concentrated under reduced pressure. After adding 70 mL of hexane, the precipitate formed is isolated by filtration to give 4.2 g of an orange-colored solid after drying. Yield: 53percent m.p.: 188-193° C. 1H NMR (CDCl3) δ: 8.15 (m, 2H), 7.65 (broad s, 1H), 7.15 (d, 1H), 1.40 (s, 9H), 1.20 (s, 12H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | at 35℃; for 18 h; Inert atmosphere | 2-Ammopyndmc-4-boromc acid pinacol cstcr (2 0 g 9 1 rnmol) was siirrcd as asuspension in ret t-hutanol 30 mL) undei an aigon atinosphete The Boc anhydride (2 20g, 10.0 mmol) in tert-butanoi (20 mL) was added slowly, and the reaction stirred at 35 °Cfor 18 hours. Analysis by H N MR showed the pinacol ester starting material had beenconsumed. The reaction mixture was concentrated under reduced pressure, and the crudematerial stirred in water fur 5 minutes. The solid was collected by filtration and dried in vacuo at 50 °C. to afford tert-hutyl 4-(4,4,5,5-tetramethy1- i ,3,2-dioxaborolan-2- yi)pyridin-2-yl)carbamate (31) as a white solid (2.9 g, 98percent); mp 172— 178.0°C.(Lit. 188193 °C). 1H NMR (200 MHz, DMSO-d6) 8 9.75 (hr s, lEO, 8.26 (di 1 H, J 0.9, 4.8 Hz),808(ni lH).,7 l8dd 111 J07 4 8Hz), 147(s 911) 131 (s 1211) |
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