[ CAS No. 443776-76-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 443776-76-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 443776-76-9 ]

SDS Specification

Alternatived Products of [ 443776-76-9 ]

Product Details of [ 443776-76-9 ]

CAS No. :	443776-76-9	MDL No. :	MFCD09266196
Formula :	C₁₃H₁₉BO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ZEWWJJQAFTXUIS-UHFFFAOYSA-N
M.W :	234.10	Pubchem ID :	44118236
Synonyms :

Calculated chemistry of [ 443776-76-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	69.05
TPSA :	38.69 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.02
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	1.14
Log Po/w (SILICOS-IT) :	1.71
Consensus Log Po/w :	1.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.69
Solubility :	0.474 mg/ml ; 0.00203 mol/l
Class :	Soluble
Log S (Ali) :	-2.46
Solubility :	0.812 mg/ml ; 0.00347 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.83
Solubility :	0.0344 mg/ml ; 0.000147 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.99

Safety of [ 443776-76-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 443776-76-9 ]

* 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 [ 443776-76-9 ]

[ 443776-76-9 ] Synthesis Path-Downstream 1~12

Yield	Reaction Conditions	Operation in experiment
43%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 85℃;Inert atmosphere;	General procedure: Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107)[0334]To a solution of compound 0601-107 (2.5 g, 11.6 mmol) and bis(pinacolato)diboron (4.4 g, 17.5 mmol) in dioxane (100 mL) was added potassium acetate (3.4 g, 35 mmol) and PdCl2(dppf)2 (0.95 g, 1.1 mmol). The mixture was degassed with nitrogen and heated at 85 C. for overnight. The reaction mixture was concentrated under reduced pressure to afford the crude product, which purified by column chromatography (ethyl acetate in petroleum ether, 15% v/v) to give the compound 0602-107 (1.55 g, 51%) as a pink solid. LCMS: 262 [M+1]+. 1H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12H), 2.03 (s, 3H), 7.30 (s, 1H), 7.31 (d, J=2.0 Hz 1H), 7.73 (d, J=2.0 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 9.93 (s, 1H).
43%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 85℃;Inert atmosphere;	General procedure: Compound in dioxane (100mL) 0601-107 (2.5g, 11.6mmol) and a solution of bis (pinacolato) diboron (4.4 g, 17.5 mmol), potassium acetate (3.4 g, 35 mmol) and and PdCl2 (dppf) 2 ( 0.95g, 1.1mmol) was added. The mixture was degassed with nitrogen and heated overnight at 85 C.. The reaction mixture was concentrated under reduced pressure to give the crude product, which was purified by column chromatography (petroleum ether in ethyl acetate, 15% v / v) to give the compound 0602-107 as a pink solid obtained (1.55 g, 51%).
	With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos; In 1,4-dioxane; at 110℃;Inert atmosphere; Sealed tube;	General procedure: Step 1. General procedure for the preparation of pinacolbornane reagents: An oven-dried vial filled with argon was charged with Pd2dba3 (2 mol%), X-Phos (4 mol%), bis(pinacolato)diboron (3 equiv.) and KOAc (3 equiv.). I ,4-Dioxane was added, followed by the addition of the aryl chloride or bromide (0.5 M in 1 ,4-dioxane). The vial was sealed, and the reaction mixture was heated to 110C until aryl halide had been completely consumed, as determined by TLC analysis. At this point the reaction mixture was allowed to cool to room temperature. The reaction solution was then filtered through a thin pad of Celite (eluting with ethyl acetate) and the eluent was concentrated under reduced pressure. The crude material so obtained purified via flash chromatography on silica gel or utilized for Step 2m the Suzuki coupling reaction, directly and without purification.

2
[ 1021913-05-2 ]
[ 443776-76-9 ]
C₂₈H₃₂BrClN₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2351 - 2358

3
[ 480425-35-2 ]
[ 443776-76-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol Procedure:To a suspension of LiAlH4 (100 mg, 2.63 mmol) in THF (30 mL) was added portion-wise at room temperature methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (200 mg, 0.76 mmol). The reaction mixture was stirred at room temperature for additional 3 h. H2O (3 mL) was added dropwise at 0 C. then the mixture was filtered and concentrated under reduced pressure to give crude (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (190 mg) which was used for next step without characterization or purification.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 3h;	To a suspension of LiAlH4 (100 mg, 2.63 mmol) in THF (30 mL) was added portion-wise at room temperature methyl 3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (200 mg, 0.76 mmol).. The reaction mixture was stirred at room temperature for additional 3 h. H20 (3 mL) was added dropwise at 0C then the mixture was filtered and concentrated under reduced pressure to give crude (3-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)phenyl)methanol (190 mg) which was used for next step without characterization or purification.

Reference： [1]Patent: US2012/309746,2012,A1 .Location in patent: Page/Page column 50
[2]Patent: WO2012/163724,2012,A1 .Location in patent: Page/Page column 77

4
[ 443776-76-9 ]
[ 1415695-25-8 ]
[ 76-05-1 ]
[ 1415694-92-6 ]

Yield	Reaction Conditions	Operation in experiment
21%		Step 2(S)-(3-(8-(6-(2-Methylpyrrolidin-1-yl)pyridin-2-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)methanol Procedure:A mixture of (S)-6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (100 mg, 0.3 mmol), <strong>[443776-76-9](3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol</strong> (84 mg, 0.36 mmol), Pd2(dba)3 (30 mg, 0.05 mmol), X-Phos (30 mg, 0.06 mmol) and Cs2CO3 (196 mg, 0.6 mmol) in dioxane/H2O (30 mL/5 mL) was stirred at reflux for 18 h under N2 atmosphere. The solvent was removed under reduced pressure and the residue purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 ml/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; gradient conditions: 50% acetonitrile/50% water (0.1% TFA, v/v) initially, and proceed to 82% acetonitrile/18% water (0.1% TFA, v/v) in a linear fashion after 9 min.) to give (S)-(3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)methanol 222-trifluoroacetate (25 mg, 21%) as a yellow solid. 1H NMR (300 MHz, CD3OD): delta 9.18 (s, 1H), 8.42 (s, 1H), 8.34 (s, 1H), 7.67 (s, 1H), 7.60-7.56 (m, 1H), 7.49-7.35 (m, 3H), 6.23 (d, 1H, J=7.8 Hz), 5.98 (d, 1H, J=8.1 Hz), 4.70 (s, 2H), 4.24-4.20 (m, 1H), 3.59-3.55 (m, 1H), 3.41-3.38 (m, 1H), 2.13-1.98 (m, 3H), 1.72-1.70 (m, 1H), 1.13 (d, 3H, J=6.3 Hz). LC/MS: 401 [M+H]+. HPLC: 100% at 214 nm, 100% at 254 nm, tR=5.54 min.
21%		A mixture of (S)-6-chloro-N-(6-(2-methylpyrrolidin- l-yl)pyridin-2-yl)-[l,2,4]triazolo[l,5-a]pyridin-8-amine (100 mg, 0.3 mmol), (3-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)phenyl)methanol (84 mg, 0.36 mmol), Pd2(dba)3 (30 mg, 0.05 mmol), X-Phos (30 mg, 0.06 mmol) and Cs2C03 (196 mg, 0.6 mmol) in dioxane/H20 (30 mL/5 mL) was stirred at reflux for 18 h under N2 atmosphere. The solvent was removed under reduced pressure and the residue purified by preparative-HPLC (Gemini 5u C18 150x21.2 mm; inject volume: 3ml/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm;gradient conditions: 50% acetonitrile/50% water (0.1% TFA, v/v) initially, and proceed to 82% acetonitrile/18% water (0.1% TFA, v/v) in a linear fashion after 9 min.) to give (S)- (3-(8-(6-(2-methylpyrrolidin- l-yl)pyridin-2-ylamino)-[l,2,4]triazolo[l,5-a]pyridin-6- yl)phenyl)methanol 222-trifluoroacetate (25 mg, 21 %) as a yellow solid. 1H NMR (300 MHz, CD3OD): delta 9.18 (s, 1H), 8.42 (s, 1H), 8.34 (s, 1H), 7.67 (s, 1H), 7.60 - 7.56 (m, 1H), 7.49 - 7.35 (m, 3H), 6.23 (d, 1H, J = 7.8 Hz), 5.98 (d, 1H, J = 8.1 Hz), 4.70 (s, 2H), 4.24 - 4.20 (m, 1H), 3.59 - 3.55 (m, 1H), 3.41 - 3.38 (m, 1H), 2.13 - 1.98 (m, 3H), 1.72 - 1.70 (m, 1H), 1.13 (d, 3H, J = 6.3 Hz). LC/MS: 401 [M + H]+. HPLC: 100 % at 214 nm, 100 % at 254 nm, tR = 5.54 min.

Reference： [1]Patent: US2012/309746,2012,A1 .Location in patent: Page/Page column 50-51
[2]Patent: WO2012/163724,2012,A1 .Location in patent: Page/Page column 78

5
[ 938443-23-3 ]
[ 443776-76-9 ]
Ku-0063794 [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1212 - 1216

6
[ 443776-76-9 ]
[ 18162-48-6 ]
[ 495402-49-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dmap; In tetrahydrofuran; at 0 - 20℃; for 24h;Inert atmosphere;	Under an argon atmosphere, DMAP (772 mg, 6.32 mmol) was slowly added over a solution of <strong>[443776-76-9]3-(hydroxymethyl)phenylboronic acid pinacol ester</strong> (1.0 g, 4.27 mmol) and TBDMSCl (900 mg, 5.98 mmol) in dry THF (20 mL) cooled at 0 C. The mixture was stirred for 24 h at 20 C. The white solid was filtered off, washed with cold THF and the organic filtrates were concentrated to dryness under vacuum. The residue was column chromatographed eluting with CH2Cl2, to obtain compound 4 as a white solid (1.06 g, yield: 71%). 1H NMR (400 MHz, CDCl3): delta 0.07 (s, 6H, Si(CH3)2), 0.92 (s, 9H, C(CH3)3), 1.32 (s, 12H, 2× OC(CH3)2), 4.73 (s, 2H, CH2O), 7.04-7.35 (m, 2H, ArH), 7.51-7.54 (m, 1H, ArH), 7.70-7.73 (m, 1H, ArH) ppm; 13C NMR (100 MHz, CDCl3): delta -5.2 (Si(CH3)2), 18.5 (C(CH3)3), 24.9 (4× CH3), 26.0 (C(CH3)3), 64.9 (CH2O), 83.6 (2× C-O), 127.6, 129.0, 132.2, 133.1, 140.4 ppm; MS m/z (%): 348 (1, M+), 291 (26), 191 (100); HRMS m/z Calcd for C19H33BO3SiNa: 371.2190, found: 371.2191.

Reference： [1]Tetrahedron,2013,vol. 69,p. 3465 - 3474

7
[ 443776-76-9 ]
[ 104-94-9 ]
[ 1454653-66-7 ]