[ CAS No. 656257-45-3 ]

Name: 656257-45-3|4-(4-Ethylpiperazin-1-yl)phenylboronic acid pinacol ester|95%
Brand: Ambeed
SKU: A491162
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Quality Control of [ 656257-45-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 656257-45-3 ]

SDS Specification

Alternatived Products of [ 656257-45-3 ]

Product Details of [ 656257-45-3 ]

CAS No. :	656257-45-3	MDL No. :	MFCD13190738
Formula :	C₁₈H₂₉BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OSJYTVPEVGWXNG-UHFFFAOYSA-N
M.W :	316.25 g/mol	Pubchem ID :	56965740
Synonyms :

Calculated chemistry of [ 656257-45-3 ]

Physicochemical Properties

Num. heavy atoms :	23
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.67
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	103.99
TPSA :	24.94 Å²

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) :	-5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.21
Log Po/w (WLOGP) :	1.37
Log Po/w (MLOGP) :	1.8
Log Po/w (SILICOS-IT) :	1.8
Consensus Log Po/w :	1.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.82
Solubility :	0.0481 mg/ml ; 0.000152 mol/l
Class :	Soluble
Log S (Ali) :	-3.41
Solubility :	0.124 mg/ml ; 0.000393 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.55
Solubility :	0.00889 mg/ml ; 0.0000281 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.3

Safety of [ 656257-45-3 ]

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:

Application In Synthesis of [ 656257-45-3 ]

* 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 [ 656257-45-3 ]
Downstream synthetic route of [ 656257-45-3 ]

[ 656257-45-3 ] Synthesis Path-Upstream 1~6

1
[ 25015-63-8 ]
[ 656257-43-1 ]
[ 656257-45-3 ]

Yield	Reaction Conditions	Operation in experiment
55.48%	With triethylamine In 1,4-dioxane for 12 h; Heating / reflux	To a solution of intermediate 3 (3g, 11mmol) in dioxane [(100MOL)] was added 4,4, 5,5- tetramethyl-1, 3, 2-dioxaborolane (1. [8MOI,] [12MOL),] dichlorobis(triphenylphosphine)palladium(II) (0.392g, 0. [57MMOL),] triethylamine [(4.] [65MOI,] 33mmol) and the mixture was heated under reflux for 12 hours and then poured into water. After extraction with CH2CI2, the organic phase was dried over [NA2SO4] and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with [CH2CI2/MEOH] (9/1). The titled compound was obtained as a brown oil which crystallised on standing (2g, 55.48percent) ; m. p. 130- [134°C.]
55.48%	With triethylamine In 1,4-dioxane for 12 h; Heating / reflux	To a solution of intermediate 25 (3g, 11mmol) in dioxane [(100ML)] was added 4,4, 5,5- tetramethyl-1, 3, 2-dioxaborolane (1. [8ML,] [12MOL),] [DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (LL)] (0.392g, 0. [57MMOL)] and triethylamine (4. [65ML, 33MMOL)] and the mixture was heated under reflux for 12 hours. On cooling, the mixture was poured into water and extracted with [CH2CI2.] The organic phase was dried over [NA2SO4] and concentrated under reduced pressure to give a residue which was purified by chromatography on silica gel eluting with [CH2CI2/MEOH] (90: 10). The titled compound was obtained as a brown oil which crystallised on standing (2g, 55.48percent) ; m. p. [130-134°C.]

Reference： [1] Patent: WO2004/13134, 2004, A2, . Location in patent: Page 27; 28
[2] Patent: WO2004/13135, 2004, A1, . Location in patent: Page 49

2
[ 61676-62-8 ]
[ 656257-43-1 ]
[ 656257-45-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: at -78 - 20℃;	1- (4-bromophenyl) -4-ethylpiperazine (300 mg, 1.11 mmol)In tetrahydrofuran (10 mL)An n-butyllithium hexane solution (1.60 M, 1.05 mL, 1.67 mmol) was added dropwise at -78 ° C.After stirring for 1 hour,A solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (270 μL, 1.34 mmol) in tetrahydrofuran (5 mL) was added dropwise.The mixture was warmed to room temperature and stirred overnight.After completion of the reaction,A saturated aqueous ammonium chloride solution was added dropwise,And extracted with chloroform.The organic layer was dried over anhydrous sodium sulfate,Filtration,And concentrated under reduced pressure.The residue was purified by silica gel column chromatography (chloroform / methanol)Made,To give the title compound (283 mg, 80percent)

Reference： [1] Patent: JP6023630, 2016, B2, . Location in patent: Paragraph 0237; 0238; 0239

3
[ 73183-34-3 ]
[ 656257-43-1 ]
[ 656257-45-3 ]

Reference： [1] Patent: WO2017/15400, 2017, A1, . Location in patent: Paragraph 0077

4
[ 589-87-7 ]
[ 656257-45-3 ]

Reference： [1] Patent: JP6023630, 2016, B2,

5
[ 5308-25-8 ]
[ 656257-45-3 ]

Reference： [1] Patent: JP6023630, 2016, B2,

6
[ 66698-28-0 ]
[ 656257-45-3 ]

Reference： [1] Patent: WO2017/15400, 2017, A1,

[ 656257-45-3 ] Synthesis Path-Downstream 1~18

1
[ 25015-63-8 ]
[ 656257-43-1 ]
[ 656257-45-3 ]

Yield	Reaction Conditions	Operation in experiment
55.48%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; for 12h;Heating / reflux;	To a solution of intermediate 3 (3g, 11mmol) in dioxane [(100MOL)] was added 4,4, 5,5- tetramethyl-1, 3, 2-dioxaborolane (1. [8MOI,] [12MOL),] dichlorobis(triphenylphosphine)palladium(II) (0.392g, 0. [57MMOL),] triethylamine [(4.] [65MOI,] 33mmol) and the mixture was heated under reflux for 12 hours and then poured into water. After extraction with CH2CI2, the organic phase was dried over [NA2SO4] and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with [CH2CI2/MEOH] (9/1). The titled compound was obtained as a brown oil which crystallised on standing (2g, 55.48%) ; m. p. 130- [134C.]
55.48%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; for 12h;Heating / reflux;	To a solution of intermediate 25 (3g, 11mmol) in dioxane [(100ML)] was added 4,4, 5,5- tetramethyl-1, 3, 2-dioxaborolane (1. [8ML,] [12MOL),] [DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (LL)] (0.392g, 0. [57MMOL)] and triethylamine (4. [65ML, 33MMOL)] and the mixture was heated under reflux for 12 hours. On cooling, the mixture was poured into water and extracted with [CH2CI2.] The organic phase was dried over [NA2SO4] and concentrated under reduced pressure to give a residue which was purified by chromatography on silica gel eluting with [CH2CI2/MEOH] (90: 10). The titled compound was obtained as a brown oil which crystallised on standing (2g, 55.48%) ; m. p. [130-134C.]

Reference： [1]Patent: WO2004/13134,2004,A2 .Location in patent: Page 27; 28
[2]Patent: WO2004/13135,2004,A1 .Location in patent: Page 49

2
[ 656257-45-3 ]
[ 1513859-36-3 ]
[ 1513857-20-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;	Example 693-(2,6-difluoro-3,5-dimethoxyphenyl)-9-14-(4-ethylpiperazin-1-yl)phenylj -1-methyl-1,3,4,7-tetrahydro-2H-pyrazolo j4?,3? : 5,6jpyrido j4,3-dj pyrimidin-2-one To a solution of 9-bromo-3 -(2,6-difluoro-3 ,5-dimethoxyphenyl)- i-methyl-i ,3 ,4,7-tetrahydro-2H-pyrazolo [4?,3 ?:5 ,6]pyrido[4,3 -d]pyrimidin-2-one (30.0 mg, 0.066 mmol) and 1-ethyl-4- [4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyl]piperazine (31.0 mg, 0.099 mmol) in 1,4-dioxane (0.75 mL) and water (0.25 mL) were added potassium carbonate (36.0 mg, 0.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.6 mg, 0.0066 mmol). The resulting mixture was heated to 100 C for 12 h before it was diluted with MeOH and purified by RP-HPLC (pH 2). LC-MS calculated for C29H32F2N703 [M+H] mlz: 564.3; found 564.3.?H NMR (300 MHz, DMSO) oe 13.8 (s, 1H), 8.27 (s, 1H), 7.42 (d, J= 9.0 Hz, 2H), 7.13 (d, J = 9.0 Hz, 2H), 7.03 (t, J= 6.0 Hz, 1H), 4.82 (s, 2H), 3.98 (d, J= 9.0 Hz, 2H), 3.88 (s, 6H), 3.59 (d, J= 9.0 Hz, 2H), 3.22-2.98 (m, 6H), 2.78 (s, 3H), 1.24 (t, J= 6.0 Hz, 3H).

Reference： [1]Patent: WO2014/7951,2014,A2 .Location in patent: Page/Page column 154; 155

3
[ 656257-45-3 ]
[ 1247001-86-0 ]
[ 1247003-79-7 ]