214973-83-8|tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate| Ambeed

Structure of 214973-83-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 214973-83-8 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 214973-83-8 ]

CAS No. :	214973-83-8
Formula :	C₁₄H₂₀BrNO₂
M.W :	314.22
SMILES Code :	O=C(OC(C)(C)C)NC(C)(C1=CC=C(Br)C=C1)C
MDL No. :	MFCD16619489
Boiling Point :	No data available
InChI Key :	CKWJIFNNVRMXFW-UHFFFAOYSA-N
Pubchem ID :	18183247

Safety of [ 214973-83-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 214973-83-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	6
Fraction Csp3	0.5
Num. rotatable bonds	5
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	77.15
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.16
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.7
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.1
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.57
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.54

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.04
Solubility	0.0289 mg/ml ; 0.0000921 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.2
Solubility	0.02 mg/ml ; 0.0000637 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.01
Solubility	0.0031 mg/ml ; 0.00000986 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.59 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.06

Application In Synthesis of [ 214973-83-8 ]

* 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 [ 214973-83-8 ]

[ 214973-83-8 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 17797-12-5 ]
[ 214973-83-8 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 16h;	MeLi (2eq) is added to a solution of 4-bromo-benzonitrile (leq) an CeCi3 (leq) in THF at -78C. The reaction is allowed to warm to room temperature. Boc anhydride is added to the reaction. The solution is allowed to stir for 16 hrs at room temperature. Water, followed by EtOAc are added. The combined organic layers are separated, dried (MgSO/i) and concentrated in vacuo to give the desired product which is purified by column chromatography.
	With triethylamine; In tetrahydrofuran; at 20℃; for 4h;	Intermediate 201 [1-(4-Bromo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester; To a solution of 1-(4-bromo-phenyl)-1-methyl-ethylamine (Intermediate 197) (1 eq, 10.8 mmol, 2.34 g) in THF (50 ml) are added TEA (1.5 eq, 16.2 mmol, 2.26 ml) and Boc2O (1.1 eq, 11.9 mmol, 2.6 g). The resulting mixture is stirred for 4 h at r.t. The solvents are evaporated, sat. aqueous NaCl solution is added, and the mixture is extracted with DCM. The combined organic layers are dried with MgSO4, filtered, and the solvents are removed under reduced pressure giving the title compound; [M+H]+=314/316.

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183.
[2]Patent: WO2010/10189,2010,A1 .Location in patent: Page/Page column 71.
[3]Patent: US2009/181941,2009,A1 .Location in patent: Page/Page column 54.

2
[ 214973-83-8 ]
[ 73183-34-3 ]
[ 335592-60-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 5h;	Step 4: Preparation of tert-butyl {1-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}carbamate A suspension of tert-butyl[1-(4-bromophenyl)-1-methylethyl]carbamate (500 mg) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (485 mg) and potassium acetate (468 mg) and PdCl2(dppf)CH2Cl2 (39 mg) in dimethylsulfoxide (8 mL) was degassed for 5 min. then stirred at 80 C. for 5 h. The reaction mixture was diluted with benzene and filtered. The filtrate was washed with brine (5 times). The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-15% ethyl acetate in hexanes) gave the product (481 mg, 84%). 1HNMR (CDCl3) 400 MHz delta: 7.77 (d, J=8.3 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 4.95 (br s, 1H), 1.61 (br s, 6H), 1.46-1.07 (m, 9H), 1.33 (s, 12H).
5.67 g	With potassium acetate; palladium diacetate; XPhos; In acetonitrile; at 75℃; for 18h;Inert atmosphere;	Step 2: tert-butyl (2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propan-2- yl)carbamate: The product from Step 1 above (6 g, 18.52 mmol, 97% purity), bis- (pinacolato)diboron (5.82 g, 22.91 mmol), palladium(II) acetate (0.107 g, 0.477 mmol), potassium acetate (5.62 g, 57.3 mmol) and XPhos (0.457 g, 0.955 mmol) were combined in MeCN (50 ml). The vessel was purged with N2 then heated at 75 C for 18 h. The reaction mixture was cooled, filtered through Celite, washing with MeCN (2 x 50 ml), and concentrated in vacuo to afford a brown oil. The residue was partitioned between DCM (50 ml) and water (50 ml). The phases were separated and the organic phase was concentrated in vacuo to afford a brown soild. The crude product was purified by columnchromatography (220 g cartridge, 0-20% EtOAc/isohexane) to afford the title compound (5.67 g, 15.1 mmol, 96% purity) as an off-white solid. LCMS (Method 1): m/z 306 (M+H- C4H8)+ at 2.83 min.

References: [1]Patent: US2012/108574,2012,A1 .Location in patent: Page/Page column 112.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183.
[3]Patent: WO2016/102672,2016,A2 .Location in patent: Page/Page column 104.

3
[ 214973-83-8 ]
[ 937366-50-2 ]