[ CAS No. 578729-21-2 ] {[proInfo.proName]}

Name: 578729-21-2|(R)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate|98%
Brand: Ambeed
SKU: A143099
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Quality Control of [ 578729-21-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 578729-21-2 ]

SDS Specification

Alternatived Products of [ 578729-21-2 ]

Product Details of [ 578729-21-2 ]

CAS No. :	578729-21-2	MDL No. :	MFCD11506010
Formula :	C₁₃H₁₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KECPRZHCNCDSET-SECBINFHSA-N
M.W :	300.19	Pubchem ID :	52987808
Synonyms :

Calculated chemistry of [ 578729-21-2 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	72.46
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.39
Log Po/w (XLOGP3) :	3.52
Log Po/w (WLOGP) :	3.71
Log Po/w (MLOGP) :	3.32
Log Po/w (SILICOS-IT) :	2.95
Consensus Log Po/w :	3.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.85
Solubility :	0.0424 mg/ml ; 0.000141 mol/l
Class :	Soluble
Log S (Ali) :	-4.01
Solubility :	0.0294 mg/ml ; 0.000098 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.62
Solubility :	0.00712 mg/ml ; 0.0000237 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.41

Safety of [ 578729-21-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 578729-21-2 ]

* 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 [ 578729-21-2 ]
Downstream synthetic route of [ 578729-21-2 ]

[ 578729-21-2 ] Synthesis Path-Upstream 1~4

1
[ 24424-99-5 ]
[ 24358-62-1 ]
[ 578729-21-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydrogencarbonate In methanol for 4 h;	(R)-N-{1-[4-(2-Ethoxy-pyridin-3-yl)-phenyl]-ethyl}-2-trifluoromethoxy-benzenesulfonamide To a solution of (R)-1-(4-bromophenyl)ethylamine (1.0 g, 5 mmol) in methanol (10 ml) was added sodium hydrogen carbonate (1.26 g, 15.0 mmol) and di-tert-butyl dicarbonate (1.2 g, 5.5 mmol). The reaction mixture was sonicated for 4 h. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure to give (R)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.8 g, 6.0 mmol, 120percent) as a white solid. To a solution of (R)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (0.73 g, 2.4 mmol) in 1,2-dimethoxyethane (10 ml) was added tetrakis (triphenylphosphine) palladium (0.14 g, 0.12 mmol), 2-chloropyridine-3-boronic acid (0.77 g, 4.9 mmol) and 2 M sodium carbonate. The reaction mixture was heated to reflux for 16 h and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was chromatographed over silica gel eluting with 3:1 heptane/ethyl acetate and the solvent removed under reduced pressure to give (R)-{1-[4-(2-chloro-pyridin-3-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (0.56 g, 1.7 mmol, 71percent) as an off white solid. A mixture of (R)-{1-[4-(2-chloro-pyridin-3-yl)-phenyl]-ethyl}carbamic acid tert-butyl ester (100 mg, 0.3 mmol), sodium ethoxide (61 mg, 0.9 mmol) and tetrahydrofuran (5 ml) was heated under reflux under an argon atmosphere for 16 h. The solvent was evaporated and the residue purified on a SCX column (eluted with 2M ammonia in methanol) chromatography to give (R)-1-[4-(2-ethoxy-pyridin-3-yl)-phenyl]-ethylamine (66 mg, 0.27 mmol, 90percent) as a yellow gum. To a solution of (R)-1-[4-(2-ethoxy-pyridin-3-yl)-phenyl]-ethylamine (13 mg, 0.05 mmol) in dichloromethane (1 ml) was added triethylamine (17 mg, 0.16 mmol) followed by 2-(trifluoromethoxy)benzenesulfonyl chloride (17 mg, 0.065 mmol). The reaction mixture was stirred for 16 h and the solvent evaporated under reduced pressure. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (6 mg, 0.013 mmol, 26percent). ¹H NMR (400 MHz, DMSO-d₆): δ 8.42 (d, 1H), 8.13 (dd, 1H), 7.81 (dd, 1H), 7.63 (m, 2H), 7.39 (m, 4H), 7.24 (d, 2H), 7.05 (m, 1H), 4.48 (q, 1H), 4.36 (q, 2H), 1.35 (d, 3H), 1.29 (t, 3H) ppm; MS (ESI) m/z: 467 [M+H]⁺.
96%	at 20℃; for 2 h;	(R)-1-(4-bromophenyl)ethanamine (14.4g, 72.0mmol) was dissolved in 60ml 46 dichloromethane (DCM), a solution of Boc₂O (17.3g, 79.2mmol, 1.1 eq) in 60ml 47 DCM was added dropwise at room temperature. The resulting solution was stirred at room temperature for further 2h after LCMS indicating completion. The mixture was concentrated and suspended in 48 hexane. The 49 solid was collected and dried under vacuum to give 20.0g white solid, yield: 92.6percent.
93%	With sodium hydroxide In 1,4-dioxane; water at 25℃;	To a stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (5g, 24.99 mmol), in dioxane (50ml_) under argon were added di-tert-butyl dicarbonate (6 g, 27.5 mmol) and NaOH 0.5 M (50 mL). The resulting solution was stirred at 25 °C overnight. The reaction mixture was partitioned between ethyl acetate and 10percent citric acid and extracted with ethyl acetate (3x100 ml). The organic phase was washed with brine (50 mL), dried over Na₂SO₄ and evaporated. The residue solidified to a white solid and was used without further purification. (7 g, 93percent). ¹H NMR (CDCI₈) 5: 1.32-1.34 (m, 12 H), 4.68-4.71 (m, 2 H), 7.29-7.12 (m, 2H), 7.36-7.39 (m, 2H). ESIMS (MH+): 302

Reference： [1] Patent: US2007/149577, 2007, A1, . Location in patent: Page/Page column 6-7
[2] European Journal of Medicinal Chemistry, 2019, p. 407 - 422
[3] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 176
[4] Patent: WO2008/68507, 2008, A2, . Location in patent: Page/Page column 57
[5] Patent: WO2009/60278, 2009, A1, . Location in patent: Page/Page column 48
[6] Patent: US2007/149577, 2007, A1, . Location in patent: Page/Page column 14
[7] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1996 - 2015
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15138 - 15142[9] Angew. Chem., 2018, vol. 130, # 46, p. 15358 - 15362,5

2
[ 24424-99-5 ]
[ 578729-21-2 ]

Reference： [1] Patent: WO2009/36996, 2009, A2, . Location in patent: Page/Page column 74

3
[ 58632-95-4 ]
[ 24358-62-1 ]
[ 578729-21-2 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 47, p. 11244 - 11252

4
[ 578729-21-2 ]
[ 73183-34-3 ]
[ 578729-05-2 ]

Reference： [1] Patent: WO2005/63690, 2005, A1, . Location in patent: Page/Page column 28
[2] Patent: US2003/220375, 2003, A1,