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[ CAS No. 286961-15-7 ] {[proInfo.proName]}

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Chemical Structure| 286961-15-7
Chemical Structure| 286961-15-7
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Product Details of [ 286961-15-7 ]

CAS No. :286961-15-7 MDL No. :MFCD11521562
Formula : C19H26BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :QDSFHRPYZPQWEJ-UHFFFAOYSA-N
M.W : 343.23 Pubchem ID :11290836
Synonyms :

Calculated chemistry of [ 286961-15-7 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.53
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 101.93
TPSA : 48.0 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.85
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 1.98
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.61
Solubility : 0.084 mg/ml ; 0.000245 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.104 mg/ml ; 0.000304 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.53
Solubility : 0.0101 mg/ml ; 0.0000294 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.95

Safety of [ 286961-15-7 ]

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:

Application In Synthesis of [ 286961-15-7 ]

* 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.

  • Upstream synthesis route of [ 286961-15-7 ]
  • Downstream synthetic route of [ 286961-15-7 ]

[ 286961-15-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 73183-34-3 ]
  • [ 286961-24-8 ]
  • [ 286961-15-7 ]
YieldReaction ConditionsOperation in experiment
78% With potassium acetate In 1,4-dioxane at 80℃; for 16 h; [1245] The title compound was prepared according to the procedure described in Tetrahedron Lett. 2000, 41 3705. Bis(pinacolato)diborane (338 mg, 1.33 mmol), potassium acetate (356 mg, 3.63 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2dppf; 30 mg, 0.04 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (20 mg, 0.04 mmol) were combined and treated with the product from Example 58A (440 mg, 1.21 mmol) in degassed 1,4-dioxane (7 mL). The reaction mixture was heated at 80° C. for 16 hours, allowed to cool to 23° C., diluted with water, and extracted with dichloromethane (3.x.). The dichloromethane extracts were combined, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on flash silica gel (20percent ethyl acetate:hexanes) to provide the title compound (323 mg, 78percent yield). 1H NMR (300 MHz, CDCl3) δ1.25 (s, 12H), 2.24 (m, 2H), 3.52 (dd, 2H, J=5.7, 5.7 Hz), 4.03 (dd, 2H, J=6 Hz), 5.14 (s, 2H), 6.46 (br m, 1H), 7.32 (m, 5H); MS (ESI) m/e 344 (M+H)+.
78% With potassium acetate In 1,4-dioxane at 80℃; for 16 h; The title compound was prepared according to the procedure described in Tetrahedron Lett. 2000, 41 3705. Bis(pinacolato)diborane (338 mg, 1.33 mmol), potassium acetate (356 mg, 3.63 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2dppf; 30 mg, 0.04 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (20 mg, 0.04 mmol) were combined and treated with the product from Example 58A (440 mg, 1.21 mmol) in degassed 1,4-dioxane (7 mL). The reaction mixture was heated at 80 C. for 16 hours, allowed to cool to 23 C., diluted with water, and extracted with dichloromethane (3). The dichloromethane extracts were combined, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on flash silica gel (20percent ethyl acetate:hexanes) to provide the title compound (323 mg, 78percent yield). 1H NMR (300 MHz, CDCl3) ? 1.25 (s, 12H), 2.24 (m, 2H), 3.52 (dd, 2H, J=5.7, 5.7 Hz), 4.03 (dd, 2H, J=3, 6 Hz), 5.14 (s, 2H), 6.46 (br m, 1H), 7.32 (m, 5H); MS (ESI) m/e 344 (M+H)+.
43.8% With potassium acetate In 1,4-dioxane at 90℃; for 16 h; Step 2 benzyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)- carboxylate (173); [0356] A mixture of bis(pinacolato)diboron (3 14 g, 12 38 mmol), 172 (5 26 g, 12 38 mmol),DPPF (0 206 g, 0 371 mmol), PdCI2(dppf)-CH2CI2 adduct (0 303 g, 0 371 mmol) and potassium acetate (2 430 g, 24 76 mmol) was heated at 90 0C in 1 ,4-dioxane (60 mL) for 16 hours It was then diluted with water (200ml) and extracted with ethyl acetate (3x), dried overNa2SO4, filtered and then purified by silica gel chromatography (Flash, 20Og silica and 10 to20percent ethyl acetate in hexanes) to give 173 (1 86 g, 5 42 mmol, 43 8 percent yield) LRMS (E-Sl)(calc ) 343 2 (found) 344 3 (MH)+
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 19, p. 3705 - 3708
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7450 - 7465
[3] Patent: US2003/229094, 2003, A1, . Location in patent: Page 76
[4] Patent: US2003/232836, 2003, A1, . Location in patent: Page 52
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 8, p. 2859 - 2872
[6] Patent: WO2008/104077, 2008, A1, . Location in patent: Page/Page column 115; 116
  • 2
  • [ 1121057-75-7 ]
  • [ 501-53-1 ]
  • [ 286961-15-7 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 20℃; for 2 h; Example 2: Tetrahydropyridine 2 was prepared in 3 steps starting with the deprotection of 1 using Method 3. The resulting HCl amine salt was dissolved in dichloromethane (0.2 M). Benzyl chloroformate (1.2 equiv) was added followed by triethylamine (3.0 equiv). The reaction was allowed to stir at room temperature for 2h after which point it was diluted with IN HCl and extracted with excess dichloromethane. The organic layer was dried over MgSψ4 and concentrated to provide the desired carbamate in quantitative yield, which was converted directly to boronic acid 2 using Method 2. [M-H]- = 260.1 m/z. Activity: B
Reference: [1] Patent: WO2010/118159, 2010, A1, . Location in patent: Page/Page column 65-66
  • 3
  • [ 1195-66-0 ]
  • [ 286961-15-7 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: With TurboGrignard In 2-methyltetrahydrofuran at -15 - -10℃;
Stage #2: at 20℃;
2nd step: under the protection of nitrogen, the 1M isopropyl magnesium chloride-lithium chloride (88 ml, 88mmol) into the reaction bottle, temperature control -15 ° C to -10 °C, dropwise N-Cbz-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, 2-methyl tetrahydrofuran (90 ml) solution, stirring finishing joining 1-2 hours. After the end of the exchange, then drop by adding methoxy boronic acid pinacone ester (14.2g, 90mmol), subsequently maintain the reaction at room temperature overnight. Adding 10percent hydrochloric acid aqueous solution quenching reaction, adjusting PH= 4-5, adding 220 ml ethyl acetate, saturated salt water an organic layer, the organic layer after evaporation to dryness, add ethanol/heptane 10:1 obtained after pulping 19.2g a buff solid N-Cbz-1, 2, 5, 6-tetrahydro-pyridine-4-boronic acid frequency that alcohol ester, GC: 99.6percent, yield: 56percent.
Reference: [1] Patent: CN105566367, 2016, A, . Location in patent: Paragraph 0020
  • 4
  • [ 19099-93-5 ]
  • [ 286961-15-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7450 - 7465
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 8, p. 2859 - 2872
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