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[ CAS No. 1415794-62-5 ] {[proInfo.proName]}

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Chemical Structure| 1415794-62-5
Chemical Structure| 1415794-62-5
Structure of 1415794-62-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1415794-62-5 ]

CAS No. :1415794-62-5 MDL No. :MFCD17677250
Formula : C16H26BClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DRSKWJMDHYDGAI-UHFFFAOYSA-N
M.W : 324.65 Pubchem ID :71093695
Synonyms :

Calculated chemistry of [ 1415794-62-5 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.62
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 101.24
TPSA : 33.73 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 : Yes
Log Kp (skin permeation) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.18
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 1.57
Log Po/w (SILICOS-IT) : 1.5
Consensus Log Po/w : 1.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.93
Solubility : 0.0385 mg/ml ; 0.000119 mol/l
Class : Soluble
Log S (Ali) : -3.56
Solubility : 0.0895 mg/ml ; 0.000276 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.49
Solubility : 0.0106 mg/ml ; 0.0000325 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.15

Safety of [ 1415794-62-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1415794-62-5 ]

* 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.

  • Downstream synthetic route of [ 1415794-62-5 ]

[ 1415794-62-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 73183-34-3 ]
  • [ 352437-09-3 ]
  • [ 1415794-62-5 ]
YieldReaction ConditionsOperation in experiment
50% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 12h; Synthesis of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine (2d): General procedure: 1-phenyl-piperazine (6.32 mL, 41.37 mmol) was dissolved in 75 mL of ethanol. This was slowly added 90 mL of a 1M Br2 in EtOH solution (90 mmol). The reaction mixture was stirred at room temperature for 15 h. The mixture was added 140 mL of water and basified using 15% aqueous NaOH. 200 mL of EtOAc was added to achieve phase separation. Afterwards the water phase was extracted with 3x75 mL EtOAc and the combined organic phases were dried and concentrated in vacuo yielding 12.99 g of crude 1-(4-bromophenyl)piperazine. When necessary the product was purified by flash chromatography using CH2Cl2:MeOH:Et3N 10:1:0.01 and concentrated in vacuo. IR: 1493, 1236, 814 cm-1. 1H-NMR (CDCl3, 300 MHz) δ: 7.32 (m, 2H), 6.77 (m, 2H), 3.11 (m, 4H), 3.03 (m, 4H). 13C-NMR (CDCl3, 300MHz) δ: 150.9, 132.0, 117.8, 111.9, 50.3, 46.2. GC-MS: 240 m/z. Mp: 121-122ºC. 1-(4-bromophenyl)piperazine (2 g, 8.29 mmol), Boc2O (1.9 g, 8.71 mmol), and sodium carbonate (1.97 g, 18.6 mmol) was dissolved in THF:Water 5:2 and refluxed for 12 h. Extraction was performed with 3x50 mL EtOAc. The combined organic phases were washed with 2x50 mL brine, dried and concentrated in vacuo. The resulting solid was purified by flash chromatography (EtOAc:Heptane 1:1) Yield: 2.04 g (72%, 5.98 mmol). 1H-NMR (CDCl3, 300 MHz) δ: 7.33 (m, 2H), 6.78 (m, 2H), 3.56 (m, 4H), 3.09 (m, 4H), 1.48 (s). 13C-NMR (CDCl3, 400 MHz) δ: 154.7, 150.2, 132.0, 118.2, 80.0, 49.3, 28.5. tert-butyl 4-(4-bromophenyl)piperazine-1-carboxylate (250 mg, 0.733 mmol), Potassium acetate (86 mg, 0.879 mmol) and Pd(dppf)Cl2 (10 mg) was dissolved in 1,4-dioxane and heated to 100 ºC with stirring. 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (223 mg, 0.879 mmol ) was then added and stirring was continued for 12 h. A crude sample was analyzed on GCMS, if the reaction was not finished a small amount of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) was added and stirring was continued for 2 hours. The reaction was then cooled to room temperature and stirred with 10 mL of brine for 10 min. The combined phases was extracted with 3x50 mL of EtOAc. The combined organic phases were dried and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc:Heptane 1:2. The pure compound was treated with 2.0 M HCl in diethyl ether and the resulting deprotected HCl salt was filtered off. Yield: 120.1 mg (50%, 0.370 mmol) 1H-NMR (CDCl3, 400 MHz) δ: 7.72 (d. 2H), 6.90 (d. 2H), 3.23 (m, 4H), 3.03 (m, 4H), 1.33 (s, 12H).
  • 2
  • [ 470478-90-1 ]
  • [ 1415794-62-5 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride; In water; ethyl acetate; at 10 - 35℃; To a stirred solution of Intermediate 1-Ill (0.8 g, 2.07 mmol) in ethyl acetate (25 mL) was added 5N HC1 (8 mL) at room temperature. The reaction mixture so obtained was stirred for 16 hours. The solid separated during the reaction was collected by filtration, washed with ethyl acetate and driedunder vacuum to give the desired product 1-5 as a white solid(0.58 g, 86%).
With hydrogenchloride; In ethyl acetate; at 20℃; for 2h;Product distribution / selectivity; (A) 1 -(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)piperazi ne hydrochlorideA solution of terf-butyl 4-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl)piperazine-1 -carboxylate (500 mg, 1 .29 mmol) in 5N HCI in EA (20 ml_) was stirred at room temperature for 2 hours, then concentrated to give curde product as a white solid.
With hydrogenchloride; In ethyl acetate; at 20℃; A solution of <strong>[470478-90-1]tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate</strong> (5.0 g, 12.9 mmol) in 5N HCl in EA (30 mL) was stirred at room temperature overnight, then concentrated to give product as a off-white solid, which was used for next step directly.
  • 3
  • [ 1400589-53-8 ]
  • [ 1415794-62-5 ]
  • [ 1415794-51-2 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110.0℃;Inert atmosphere; (A) (S)-terf -butyl 2-((7-(4-(piperazi n-1 -yl)phenyl)pyrido[4,3-£>]pyrazi n-5- ylami no)methyl)morpholi ne-4-carboxylateA solution of (S)-ferf-butyl 2-((7-chloropyrido[4,3-£>]pyrazin-5- ylamino)nnethyl)nnorpholine-4-carboxylate (3.96 g, 10.43 mmol), 1 -(4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)piperazine hydrochloride (4.4 g, 13.55 mmol), Pd(PPh3) (2.41 g, 2.09 mmol) and Cs2CO3 (10.19 g, 31 .29 mmol) in 150 mL of dioxane and 3 mL of water, under N2, was stirred at 1 10 C overnight. The volatiles were removed in vacuo, and the residues was purified by chromatography with MeOH/H2O ( 1 :20~5:1 ) to give 4.747 g of title compound. MS (m/z) = 506 (M+H)+.
  • 4
  • [ 1415794-62-5 ]
  • [ 75-36-5 ]
  • [ 1218791-38-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In tetrahydrofuran at 20℃; 54.B 1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)ethanone To a solution of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) piperazine hydrochloride (419 mg, 1.29 mmol) and cesiumcarbonate (1.27 g, 3.9 mmol) in THF (30 mL) was added acetyl chloride (0.5 mL, 6.5 mmol). Then the mixture was stirred at room temperature overnight, extracted with EA, washed with NaHCO3 solution and brine. The organic solution was concentrated and purified by flash column chromatography, eluting with PE/EA, to give product as a white solid. MS (m/z): 331 (M+H)+.
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