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CAS No. : | 1256784-52-7 | MDL No. : | MFCD14582651 |
Formula : | C20H30BNO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IIQHCFMPFOYEGW-UHFFFAOYSA-N |
M.W : | 375.27 | Pubchem ID : | 66820441 |
Synonyms : |
|
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.65 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 109.63 |
TPSA : | 57.23 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) : | -6.22 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.34 |
Log Po/w (WLOGP) : | 2.58 |
Log Po/w (MLOGP) : | 1.75 |
Log Po/w (SILICOS-IT) : | 2.13 |
Consensus Log Po/w : | 1.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.17 |
Solubility : | 0.0253 mg/ml ; 0.0000674 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.22 |
Solubility : | 0.0227 mg/ml ; 0.0000604 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.75 |
Solubility : | 0.00675 mg/ml ; 0.000018 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.85 |
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 |
---|---|---|
100% | With potassium acetate In dimethyl sulfoxide at 80℃; for 1.5 h; | 1,1-Dimethylethyl 7-bromo-2,3-dihydro-l,4-benzoxazepine-4(5H)- carboxylate (reagent preparation 21) (5.0 g, 20.1 mmol), bis(pinacolato)diboron (5.6 g, 22.1 mmol), potassium acetate (5.9 g, 60.2 mmol) and [1,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (440 mg, 0.62 mmol) were heated in DMSO (5 mL) solution at 80 0C for 1.5 h. The mixture was then cooled to room temperature and diluted with an excess of ethyl acetate and filtered through a bed of celite. The filtrate was partitioned with IM aqueous hydrochloric acid and the organic phase washed with brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated and the residue purified by silica chromatography using 4: 1 hexanes:ethyl acetate as eluent to give tert-butyl 7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzoxazepine-4(5)-carboxylate (7.6g, 100percent). 1H NMR (400 MHz, CDCl3): 7.77 (s, 0.4H), 7.67 (s, IH), 7.65 (s, 0.6H), 7.04- 6.98 (m, IH), 4.54 (s, 0.7H), 4.43 (s, 1.3H), 4.09-4.01 (m, 2H), 3.79 (dd, 2H), 1.40 (br s, 9H), 1.26 (s, 12H). MS (EI) for C20H30BNO5: 376 (MH+). |
100% | With potassium acetate In dimethyl sulfoxide at 80℃; for 1.5 h; | STEP 1 : 1,1 -Dimethylethyl 7-bromo-2,3-dihydro- 1 ,4-benzoxazepine-4(5H)- carboxylate (reagent preparation 13) (5.0 g, 20.1 mmol), bis(pinacolato)diboron (5.6 g, 22.1 mmol), potassium acetate (5.9 g, 60.2 mmol) and [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (440 mg, 0.62 mmol) were heated in DMSO (5 mL) solution at 8O0C for 1.5 h. The mixture was then cooled to room temperature and diluted with an excess of ethyl acetate and filtered through a bed of celite. The filtrate was partitioned with IM aqueous hydrochloric acid and the organic phase washed with brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated and the residue purified by silica chromatography using 4:1 hexanes:ethyl acetate as eluent to give tert-butyl 7-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-2,3-dihydrobenzoxazepine-4(5H)-carboxylate (7.6g, 100percent). 1H NMR (400 MHz, CDCl3): 7.77 (s, 0.4H), 7.67 (s, IH), 7.65 (s, 0.6H), 7.04-6.98 (m, IH), 4.54 (s, 0.7H), 4.43 (s, 1.3H), 4.09-4.01 (m, 2H), 3.79 (dd, 2H), 1.40 (br s, 9H), 1.26 (s, 12H). MS (EI) for C20H30BNO5: 376 (MH+). |
100% | With potassium acetate In dimethyl sulfoxide at 80℃; for 1.5 h; | 1,1 -Dimethylethyl 7-bromo-2,3-dihydro- 1 ,4-benzoxazepine-4(5Η)- carboxylate (5.0 g, 20.1 mmol), bis(pinacolato)diboron (5.6 g, 22.1 mmol), potassium acetate (5.9 g, 60.2 mmol) and [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (440 mg, 0.62 mmol) were heated in DMSO (5 mL) solution at 80 0C for 1.5 h. The mixture was then cooled to room temperature and diluted with an excess of ethyl acetate and filtered through a bed of celite. The filtrate was partitioned with IM aqueous hydrochloric acid and the organic phase washed with brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated and the residue purified by silica chromatography using 4:1 hexanes:ethyl acetate as eluent to give tert-butyl 7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-2,3-dihydrobenzoxazepine-4(5)-carboxylate (7.6g, 100percent). 1H NMR (400 MHz, CDCl3): 7.77 (s, 0.4H), 7.67 (s, IH), 7.65 (s, 0.6H), 7.04-6.98 (m, IH), 4.54 (s, 0.7H), 4.43 (s, 1.3H), 4.09-4.01 (m, 2H), 3.79 (dd, 2H), 1.40 (br s, 9H), 1.26 (s, 12H). MS (EI) for C20H30BNO5: 376 (MH+). |
78% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 3 h; Inert atmosphere | To a solution of tert-butyl 7-bromo-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)carboxylate(800 mg,2.44 mmol)in 1,4-dioxane (5 mL)was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)(1.24 g,4.88 mmol),KOAc (718 mg,7.31 mmol)and [1,1'bis(diphenylphosphino)ferrocene]dichloropalladium(II)(178 mg,0.24 mmol). The mixture was15 heated to 90 oc for 3 h under a nitrogen atmosphere. After cooling to room temperature,EtOAc(60 mL)was added and washed with water (50 mL x 2). The organic layer was dried over anhydrous Na2S04,filtered and concentrated in vacuo. The crude residue was purified by silicagel column chromatography (petroleum ether/EtOAc = 3: 1)to give the title compound (71 0 mg,78percent)as a white solid. LCMS M/Z (M+Na)398. |
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