[ CAS No. 360792-43-4 ] {[proInfo.proName]}

Name: 360792-43-4|tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate|95%
Brand: Ambeed
SKU: A411705
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Quality Control of [ 360792-43-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 360792-43-4 ]

Product Details of [ 360792-43-4 ]

CAS No. :	360792-43-4	MDL No. :	MFCD22415459
Formula :	C₁₉H₃₀BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MGDIIQXOACAHIU-UHFFFAOYSA-N
M.W :	347.26	Pubchem ID :	20806728
Synonyms :

Calculated chemistry of [ 360792-43-4 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.63
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	101.24
TPSA :	56.79 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) :	-5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.87
Log Po/w (WLOGP) :	3.05
Log Po/w (MLOGP) :	2.07
Log Po/w (SILICOS-IT) :	2.64
Consensus Log Po/w :	2.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.15
Solubility :	0.0248 mg/ml ; 0.0000713 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.76
Solubility :	0.00604 mg/ml ; 0.0000174 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.72
Solubility :	0.000662 mg/ml ; 0.00000191 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.4

Safety of [ 360792-43-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 360792-43-4 ]

* 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 [ 360792-43-4 ]

[ 360792-43-4 ] Synthesis Path-Downstream 1~50

1
[ 360792-43-4 ]
2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylamine; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogenchloride at 20℃; for 0.5h;

Reference： [1]Lazarova, Tsvetelina I.; Jin, Lei; Rynkiewicz, Michael; Gorga, Joan C.; Bibbins, Frank; Meyers, Harold V.; Babine, Robert; Strickler, James [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 5022 - 5027]

2
[ 120157-97-3 ]
[ 73183-34-3 ]
[ 360792-43-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 18h;	A mixture of tert-butyl 4-bromophenethylcarbamate (C48) (0.68 g, 2.3 mmol), bis(pinacolato)diborane (0.89 g, 3.5 mmol), potassium acetate (0.69 g, 7.0 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.10 g, 0.14 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (0.075 g, 0.14 mmol) in anhydrous dioxane (7 mL) was heated at 80 C. for 18 hours. The reaction was cooled, diluted with ethyl acetate, and washed with water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The crude compound was adsorbed onto silica gel and purified by flash column chromatography using 0-60% ethyl acetate/hexanes as eluent to afford the title compound as a clear oil (0.86 g, 104%): 1H NMR (400 MHz, CDCl3) delta 7.75 (d, J=7.9 Hz, 2H), 7.23-7.17 (m, 2H), 4.51 (s, 1H), 3.46-3.28 (m, 2H), 2.81 (t, J=7.1 Hz, 2H), 1.43 (s, 9H), 1.34 (s, 12H); ESIMS m/z 348 ([M+H]+).
85%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 120℃; for 12h;Inert atmosphere;	Under argon protection,Compound (h) (600 mg, 2.0 mmol) was added sequentially to a 50 mL two-necked flask.Anhydrous potassium acetate (588 mg, 6 mmol),Diterpenoid borate (607mg, 2.4mmol) and PdCl2 (dppf)(44mg, 0.06mmol),Add 20 mL of anhydrous dioxane (1:1 by volume),The mixture was reacted at 120 C for 12 hours.After the reaction was completed, it was cooled to room temperature. Filtered with suction and the filtrate was extracted with ethyl acetate.Wash with water and wash with saturated NaCl.The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure.Separation by column method, eluent:Petroleum ether (PE) / ethyl acetate (EA) = (20:1),A white solid (566 mg, 85%) was obtained.
40.58 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; at 65℃; for 16h;	Dissolved <strong>[120157-97-3]tert-butyl N-[2-(4-bromophenyl)ethyl]carbamate</strong> (?124.95 mmol) in THF (500 mL). Added bis(pinacolato)diboron (44.0 g, 174.93 mmol), palladium chloride diphenyl phosphine ferrocene (10.2 g, 10 mol %) and potassium acetate (36.8 g, 374.85 mmol). Heated to 65 C. for 16 hours. Removed solvent and purified using normal phase chromatography (0-100% EtOAc in heptanes) to yield 40.58 g of product; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.35 (s, 12H) 1.44 (s, 9H) 2.82 (t, J=6.74 Hz, 2H) 3.38 (d, J=5.86 Hz, 2H) 4.18-4.71 (m, 1H) 7.21 (d, J=7.42 Hz, 2H) 7.76 (d, J=7.61 Hz, 2H).

Reference： [1]Patent: US2014/274688,2014,A1 .Location in patent: Paragraph 0374; 0375
[2]Patent: CN108794490,2018,A .Location in patent: Paragraph 0070; 0071; 0072
[3]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 635 - 640
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5022 - 5027
[5]Patent: US10239885,2019,B1 .Location in patent: Page/Page column 18

3
[ 360792-43-4 ]
[ 913181-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / aq. HCl / 0.5 h / 20 °C 2: 88 percent / diisopropylethylamine / dimethylformamide / 18 h / 20 °C

4
[ 360792-43-4 ]
<i>N</i>-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-guanidine; compound with trifluoro-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / aq. HCl / 0.5 h / 20 °C 2: 88 percent / diisopropylethylamine / dimethylformamide / 18 h / 20 °C 3: 94 percent / 5 h / 20 °C

5
[ 360792-43-4 ]
[ 360791-97-5 ]
(tert-butoxy)-N-(2-{4-[4-(1-methyl-2-[(methylethyl)sulfonyl]amino}ethoxy)phenyl]phenyl}ethyl)carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium carbonate In 1,2-dimethoxyethane; water at 85℃; Heating / reflux;	38 Preparation of Final Title Compound. EXAMPLE 38 ; Preparation of (tert-butoxy)-N-(2-{4-[4-(1-methyl-2-[(methylethyl)sulfonyl]amino}ethoxy)phenyl]phenyl}ethyl)carboxamide. ; [2-(4-Bromophenoxy)propyl][(methylethyl)sulfonyl]amine (1.875 g, 5.576 mmol, prepared in example 1), 4-{2-[(tert-butoxy)carbonylamino]ethyl}boronic acid, pinacol ester, (2.26 g, 6.508 mmol), dichlorobis(triphenylphosphine)palladium(II) (155 mg, 0.221 mmol), 2M sodium carbonate (1.96 g in 9.25 mL water) and 1,2-dimethoxyethane (36 mL) were combined in a 100 mL 3-neck round bottom flask, fitted with a condenser, stirbar, and thermometer, and heat at reflux in a nitrogen system to 85 C. overnight. The room temperature reaction mixture was quenched with water and extracted three times with 25 mL of methylene chloride. The organic extracts were combined, dried over anyhydrous magnesium sulfate, filtered through celite, and concentrated under reduced pressure, yielding 4.0 g brown viscous oil. This material was purified via silica gel chromatography, utilizing a Hewlett-Packard HPLC 2000 with 2 silica cartridges in a 1:1 hexane:ethyl acetate solvent system, yielding the final title compound (610 mg, 29%), (tert-butoxy)-N-(2-{4-[4-(1-methyl-2-[(methylethyl)sulfonyl]amino}ethoxy)phenyl]phenyl}ethyl)carboxamide, as a white solid. ; Electrospray-MS 477.0 (M*+1).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2003/225266, 2003, A1 Location in patent: Page 30

6
[ 360792-42-3 ]
[ 360792-43-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium carbonate In propan-1-ol; diethyl ether for 2h;	38 Preparation of 4-{2-[(tert-butoxy)carbonylamino]ethyl}boronic acid, pinacol ester. Preparation of 4-{2-[(tert-butoxy)carbonylamino]ethyl}boronic acid, pinacol ester. To a stirred solution of of tert-butyl {2,2,2-trifluoro-N-[2-(4-(boronic acid)phenyl)ethyl]acetylamino}formate, pinacol ester (125 g, 0.282 mol) in n-propanol (750 ML) and diethyl ether (150 ML) was added a solution of sodium carbonate (44.8 g, 0.423 mol) in water (500 ML).After 2 h, HPLC analysis indicated nearly complete hydrolysis of the trifluoroacetamide group.The aqueous phase was separated and the organic phase was concentrated to a thick white paste.This paste was suspended in pentane and filtered.The filtrate was similarly concentrated, resuspended in pentane/diethyl ether (1:1) and filtered to afford white solids.The crops were combined and dried under reduced pressure to give 106 g (108%) of intermediate title compound, 4-{2-[(tert-butoxy)carbonylamino]ethyl}boronic acid, pinacol ester as a white powder. (CDCl3, 300 MHz): δ7.67 (d, 2H, J=4.8); 7.24 (d, 2H, J=4.5); 6.01 (br s, 1H); 3.30 (q, 2H, J=4.2); 2.81 (t, 2H, J=4.2); 1.39 (s, 9H); 1.32 (s, 12H).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2003/225266, 2003, A1 Location in patent: Page 29

7
[ 24424-99-5 ]
[ 360792-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 - 24 °C 2: 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 18 h / 80 °C
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C 2: potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 120 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / tetrahydrofuran / 16 h / 65 °C
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / tetrahydrofuran / 16 h / 65 °C

Reference： [1]Current Patent Assignee: CORTEVA INC - US2014/274688, 2014, A1
[2]Liao, Yi; Xu, Liping; Ou, Siyu; Edwards, Holly; Luedtke, Daniel; Ge, Yubin; Qin, Zhihui [ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 635 - 640]
[3]Current Patent Assignee: LANZHOU UNIVERSITY - CN108794490, 2018, A
[4]Current Patent Assignee: PERMIRA HOLDINGS LIMITED - US10239885, 2019, B1
[5]Current Patent Assignee: PERMIRA HOLDINGS LIMITED - WO2020/160075, 2020, A1

8
[ 73918-56-6 ]
[ 360792-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 - 24 °C 2: 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 18 h / 80 °C
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C 2: potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 120 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / tetrahydrofuran / 16 h / 65 °C
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / tetrahydrofuran / 16 h / 65 °C

9
[ 360792-43-4 ]
(Z)-1-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / 1,4-dioxane; water / 0.5 h / 140 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 0 - 24 °C 3: caesium carbonate / acetonitrile / 3 h / 20 - 24 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CORTEVA INC - US2014/274688, 2014, A1

10
[ 360792-43-4 ]
2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / 1,4-dioxane; water / 0.5 h / 140 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 0 - 24 °C

Reference： [1]Current Patent Assignee: CORTEVA INC - US2014/274688, 2014, A1

11
[ 360792-43-4 ]
para-toluenesulfonic acid (Z)-1-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / 1,4-dioxane; water / 0.5 h / 140 °C / Microwave irradiation 2.1: trifluoroacetic acid / dichloromethane / 0 - 24 °C 3.1: caesium carbonate / acetonitrile / 3 h / 20 - 24 °C / Inert atmosphere 4.1: isopropyl alcohol / 0.33 h / 50 °C 4.2: 50 °C

Reference： [1]Current Patent Assignee: CORTEVA INC - US2014/274688, 2014, A1

12
[ 360792-43-4 ]
[ 1417885-96-1 ]
tert-butyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In 1,4-dioxane; water at 140℃; for 0.5h; Microwave irradiation;	54 Preparation of tert-butyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethylcarbamate (C50) A mixture of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C1) (0.55 g, 1.8 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl carbamate (C49) (0.63 mg, 1.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.21 g, 0.18 mmol), and sodium bicarbonate (0.33 g, 3.9 mmol) in dioxane/water (16 mL, 3:1) in a 20 mL vial was capped and heated at 140° C. for 30 minutes in a Biotage Initiator microwave reactor with external IR-sensor temperature monitoring from the side of the vessel. The reaction was diluted with ethyl acetate and washed with water. The aqueous layers were extracted with ethyl acetate (2*), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was loaded onto a Celite cartridge and purified by flash column chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes, as eluent to provide the title compound as a white solid (0.48 g, 60%): mp 149-151° C.; 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.13 (d, J=8.1 Hz, 2H), 7.84-7.76 (m, 2H), 7.42-7.35 (m, 2H), 7.31 (d, J=7.9 Hz, 2H), 4.55 (s, 1H), 3.51-3.34 (m, 2H), 2.87 (t, J=7.0 Hz, 2H), 1.44 (s, 9H); 19F NMR (376 MHz, CDCl3) δ -58.03; ESIMS m/z 449 ([M+H]+).

Reference： [1]Current Patent Assignee: CORTEVA INC - US2014/274688, 2014, A1 Location in patent: Paragraph 0376; 0377

13
[ 360792-43-4 ]
[ 138500-90-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Cooling with ice;

Reference： [1]Liao, Yi; Xu, Liping; Ou, Siyu; Edwards, Holly; Luedtke, Daniel; Ge, Yubin; Qin, Zhihui [ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 635 - 640]

14
[ 360792-43-4 ]
[(Methylethyl)sulfonyl](2-{4-[4-(2-[(methylethyl)sulfonyl]amino}ethyl)phenyl]phenoxy}propyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 85 °C / Heating / reflux 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C