1187932-25-7|(R)-tert-Butyl (1-(3-bromophenyl)ethyl)carbamate| Ambeed

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 [ 1187932-25-7 ] Purity: 97% 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 [ 1187932-25-7 ]

CAS No. :	1187932-25-7
Formula :	C₁₃H₁₈BrNO₂
M.W :	300.19
SMILES Code :	O=C(OC(C)(C)C)N[C@@H](C1=CC=CC(Br)=C1)C
MDL No. :	MFCD12913696
InChI Key :	WWNQMGYJYMXOEU-SECBINFHSA-N
Pubchem ID :	67959607

Safety of [ 1187932-25-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 1187932-25-7 ] Show Less

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 ? 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.	3.11
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	3.52
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.71
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.	3.32
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	2.95
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.32

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.85
Solubility	0.0424 mg/ml ; 0.000141 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.01
Solubility	0.0294 mg/ml ; 0.000098 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	-4.62
Solubility	0.00712 mg/ml ; 0.0000237 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.	-5.63 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)	2.53

Application In Synthesis of [ 1187932-25-7 ]

* 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 [ 1187932-25-7 ]

[ 1187932-25-7 ] Synthesis Path-Downstream 1~35

1
[ 1187932-25-7 ]
[ 7486-35-3 ]
[ 1381813-33-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	bis-triphenylphosphine-palladium(II) chloride; In toluene; at 60℃; for 16h;Inert atmosphere;	Compound 16b: [(R)-1-(3-Vinyl-phenyl)-ethyl]-carbamic acid iert-butyl ester; A solution of [(R)-1 -(3-bromo-phenyl)-ethyl]-carbamic acid te/t-butyl ester (10.26 g, 0.0342 mol.) and tributyl(vinyl)stannane (32.5 g, 30ml_, 0.103 mol.) in toluene (175 mL) was purged with nitrogen for 30 minutes before addition of bis(triphenylphosphine palladium II chloride (2.38 g, 0.0034 mol.). The stirred mixture was heated to 60 C for 16 hours before cooling to room temperature. The reaction mixture was filtered through hyflo-supercel then evaporated to give a dark coloured oil. The oil was purified by silica gel chromatography using /so-hexanes/ethyl acetate 19:1 to yield the title compound (6.95 g, 82%) as a yellow oil. H NMR (300 MHz, CDCI3) deltalambda .39-1 .51 (m, 12H), 4.80 {br s, 2H), 5.24-5.32 (m, 1 H), 5.77 (d, J = 17.6 Hz, 1 H), 6.73 (dd, J = 17.6, 10.9 Hz, 1 H), 7.18-7.36 (m, 4H).
82%		Compound 1 i Synthesis of Compound 1i: A solution of 1 h (10.26 g, 0.0342 mol.) and tributyl(vinyl)stannane (32.5 g, 30ml_, 0.103 mol.) in toluene (175 mL) was purged with nitrogen for 30 minutes before addition of bis(triphenylphosphine palladium(ll) dichloride (2.38 g, 0.0034 mol). The stirred mixture was heated to 60 C for 16 h before cooling to room temperature. The reaction mixture was filtered through hyflo-supercel then evaporated to give a dark colored oil. The oil was purified by silica gel chromatography using /'so-hexane/ethyl acetate 19:1 to yield the title compound (6.95 g, 82%) as a yellow oil.
82%	With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 60℃; for 16h;Inert atmosphere;	A solution of 1 g (10.26 g, 0.0342 mol.) and tributyl(vinyl)tin (32.5 g, 30 mL, 0.103 mol.) in toluene (175 mL) was purged with nitrogen for 30 min before addition of bis(triphenylphosphine) palladium (II) dichloride (2.38 g, 0.0034 mol.). The stirred mixture was heated to 60C for 16 h before cooling to RT. The reaction mixture was filtered through hyflo-supercel then evaporated to give a dark coloured oil. The oil was purified by silica gel chromatography using iso- hexanes/ethyl acetate 19:1 to yield the title compound (6.95 g, 82%) as a yellow oil

82%

With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 60℃; for 16.5h;Inert atmosphere;

A solution of 1g (10.26 g, 0.0342 mol.) and tributyl(vinyl)tin (32.5 g, 30 mL, 0.103 mol.) in toluene (175 mL) was purged with nitrogen for 30 min before addition of bis(triphenylphosphine) palladium (II) dichloride (2.38 g, 0.0034 mol.). The stirred mixture was heated to 60 C. for 16 h before cooling to RT. The reaction mixture was filtered through hyflo-supercel then evaporated to give a dark coloured oil. The oil was purified by silica gel chromatography using iso-hexanes/ethyl acetate 19:1 to yield the title compound (6.95 g, 82%) as a yellow oil.

References: [1]Patent: WO2012/78915,2012,A1 .Location in patent: Page/Page column 90-91.
[2]Patent: WO2013/185093,2013,A1 .Location in patent: Page/Page column 62.
[3]Patent: WO2013/185103,2013,A1 .Location in patent: Page/Page column 63; 64.
[4]Patent: US2017/190737,2017,A1 .Location in patent: Paragraph 0207.

2
[ 24424-99-5 ]
[ 176707-77-0 ]
[ 1187932-25-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 20℃;	Example 16, Compound 16; (E)-(2R,5S,11 S,14S,17R,18R)-11 -(3-Hydroxy-benzyl)-14-isopropyl-18-methoxy- 2,17-dimethyl-3,9,12,15,28-pentaaza-tricyclo[21.3.1.1 5,9]octacosa- 1 (27),21 ,23,25-tetraene-4,10,13,16-tetraone.; Com ound 16a: [(R)-1 -(3-Bromo-phenyl)-ethyl]-carbamic acid iert-butyl esterA solution of (R)-bromo-a-methylbenzylamine (1 .023 g, 5.1 12 mmol) indichloromethane (20 mL) was subsequently treated with triethylamine (720 muIota_, 5.1 12 mmol) and di-te/t-butyl dicarbonate (1 .784 g, 8.179 mmol). After overnight stirring at room temperature, the volatiles were removed in vacuo and the residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of /so-hexanes/Et20 1 :0 to 4:1 to afford the title compound (1 .552 g, 100%) as a white solid. H NMR (300 MHz, CDCI3) 1 .43 (br s, 12H), 4.77 (br s, 2H), 7.16-7.26 (m, 2H), 7.39 (dt, J = 2.0, 7.1 Hz, 1 H), 7.46 (s, 1 H).
100%	With triethylamine; In tetrahydrofuran; at 20℃; for 3h;	00198] To a solution of (R)-l-(3-bromophenyl)ethanamine (100 mg, 0.500 mmol) in tetrahydrofuran (4 mL) was added Et3N (0.104 mL, 0.750 mmol), followed by di- tert-butyl dicarbonate (131 mg, 0.600 mmol). The reaction mixture was stirred at rt for 3 h. The solvent was removed under reduced pressure. The crude residue was diluted with Et20 and washed with IN HC1, H20 then dried over Na2S04. The Et20 layer was concentrated in vacuum to give the crude Intermediate 33A (150 mg, 0.500 mmol, 100 % yield). LC-MS (ESI) m/z 245.9 (M-Boc+H), RT = 2.13 min (Method
100%	With triethylamine; In tetrahydrofuran; at 20℃; for 3h;	To a solution of (R)-l-(3-bromophenyl)ethanamine (0.10 g, 0.50 mmol) in tetrahydrofuran (4 mL) was added Et3 (0.10 mL, 0.75 mmol), followed by di-tert-butyl dicarbonate (0.13 g, 0.60 mmol). The reaction mixture was stirred at rt for 3 h. The solvent was removed under reduced pressure. The crude residue was diluted with Et20 and washed with 1 N HC1, H20 then dried over a2S04. The Et20 layer was concentrated in vacuum to give the crude Intermediate 10A (150 mg, 0.500 mmol, 100% yield). LC-MS (ESI) m/z 245.9 (M-Boc+H), RT = 2.13 min (Method B).

100%	With triethylamine; In dichloromethane; at 20℃;	Compound 1 h Synthesis of Compound 1h: A solution of (R)-bromo-a-methylbenzylamine (1.023 g, 5.1 12 mmol) in dichloromethane (20 ml.) was subsequently treated with triethylamine (720 muIota_, 5.1 12 mmol) and di-ferf-butyl dicarbonate (1 .784 g, 8.179 mmol). After overnight stirring at room temperature, the volatiles were removed in vacuo and the residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of iso- hexane/diethyl ether 1 :0 to 4:1 to afford the title compound (1 .552 g, 100%) as a white solid
100%	With triethylamine; In dichloromethane; at 20℃;	A solution of (R)-bromo-a-methylbenzylamine (1 .023 g, 5.1 12 mmol) in dichloromethane (20 mL) was subsequently treated with triethylamine (720 mu, 5.1 12 mmol) and di-ferf-butyl dicarbonate (1.784 g, 8.179 mmol). After overnight stirring at RT, the volatiles were removed in vacuo and the residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of /'so-hexanes/diethyl ether 1 :0 to 4:1 to afford the title compound (1 .552 g, 100%) as a white solid
100%	With triethylamine; In dichloromethane; at 20℃;	A solution of (R)-bromo-alpha-methylbenzylamine (1.023 g, 5.112 mmol) in dichloromethane (20 mL) was subsequently treated with triethylamine (720 muL, 5.112 mmol) and di-tert-butyl dicarbonate (1.784 g, 8.179 mmol). After overnight stirring at RT, the volatiles were removed in vacuo and the residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/ diethyl ether 1:0 to 4:1 to afford the title compound (1.552 g, 100%) as a white solid.
84%	In dichloromethane; at 20℃; for 1h;	Compound 6a Synthesis of Compound 6a: A solution of (R)-bromo-a-methylbenzylamine (2.0 g, 10 mmol) in dichloromethane (20 mL) was treated with a solution of di-ferf-butyl dicarbonate (2.4 g, 1 1 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred at room temperature for 1 h. The solution was washed with 2 M hydrochloric acid, water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography using a gradient of /'so-hexane/ethyl acetate 20:1 to 6:1 to afford the title compound (2.51 g, 84%) as a white solid.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;	Boc-anhydride (3.71 ml, 16.0 mmol) was added to a solution of (R)-1-(3- bromophenyl)ethanamine (CAS 176707-77-0) (2.0 g, 10.0 mmol) and DIEA (1.83 ml, 10.5 mmol) in DCM (40.0 ml) at room temperature. After stirring overnight the reaction was purified directly by flash chromatography (100% DCM) to provide the title compound. 1H NMR (400 MHz, DMSO-c/6) delta ppm 7.49 (s, 1 H) 7.35 - 7.46 (m, 2 H) 7.20 - 7.35 (m, 2 H) 4.49 - 4.68 (m, 1 H) 1.18 - 1.49 (m, 12 H).

References: [1]Patent: WO2012/78915,2012,A1 .Location in patent: Page/Page column 90.
[2]Patent: WO2013/48942,2013,A1 .Location in patent: Paragraph 00198.
[3]Patent: WO2013/151923,2013,A1 .Location in patent: Paragraph 00186.
[4]Patent: WO2013/185093,2013,A1 .Location in patent: Page/Page column 61; 62.
[5]Patent: WO2013/185103,2013,A1 .Location in patent: Page/Page column 63.
[6]Patent: US2017/190737,2017,A1 .Location in patent: Paragraph 0206.
[7]Patent: WO2013/185093,2013,A1 .Location in patent: Page/Page column 76; 77.
[8]Patent: WO2015/9977,2015,A1 .Location in patent: Page/Page column 115.

3
[ 1187932-25-7 ]
[ 1381809-17-1 ]

References: [1]Patent: WO2012/78915,2012,A1 .

4
[ 1187932-25-7 ]
[ 1381813-39-3 ]

References: [1]Patent: WO2012/78915,2012,A1 .
[2]Patent: WO2013/185093,2013,A1 .
[3]Patent: WO2013/185103,2013,A1 .
[4]Patent: US2017/190737,2017,A1 .

5
[ 1187932-25-7 ]
[ 1381813-48-4 ]

References: [1]Patent: WO2012/78915,2012,A1 .

6
[ 1187932-25-7 ]
[ 1381813-63-3 ]

References: [1]Patent: WO2012/78915,2012,A1 .

7
[ 31166-44-6 ]
[ 1187932-25-7 ]
[ 865-48-5 ]
[ 1429187-90-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 70℃; for 16h;	[00199] To a suspension of Intermediate 33 A (50 mg, 0.167 mmol) and Pd2(dba)3 (15.25 mg, 0.017 mmol) in toluene (2 mL) was added xantphos (28.9 mg, 0.050 mmol), benzyl piperazine-l-carboxylate (36.7 mg, 0.167 mmol), followed by sodium tert-butoxide (48.0 mg, 0.500 mmol). The reaction mixture was stirred at 70 C for 16 h, and then filtered. The filtrate was concentrated and purified on ISCO using a 15 min gradient from 0 to 100% EtOAc in hexane to give Intermediate 33B (70 mg,0.159 mmol, 96 % yield). LC-MS (ESI) m/z 440.1 (M+H), RT = 2.27 min (Method B).

References: [1]Patent: WO2013/48942,2013,A1 .Location in patent: Paragraph 00199.

8
[ 1187932-25-7 ]
[ 1429187-89-2 ]

References: [1]Patent: WO2013/151923,2013,A1 .
[2]Patent: WO2013/48942,2013,A1 .

9
[ 1187932-25-7 ]
[ 1466528-31-3 ]

References: [1]Patent: WO2013/151923,2013,A1 .

10
[ 1187932-25-7 ]
(R)-1-(3-(1-phenethyl-1H-pyrazol-4-yl)phenyl)ethanamine hydrochloride [ No CAS ]

References: [1]Patent: WO2013/151923,2013,A1 .

11
[ 31166-44-6 ]
[ 1187932-25-7 ]
[ 1429187-90-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 70℃; for 16h;	To a suspension of Intermediate 10A (50 mg, 0.17 mmol) and Pd2(dba)3 (15 mg, 0.017 mmol) in toluene (2 mL) was added Xantphos (29 mg, 0.050 mmol), benzyl piperazine-l-carboxylate (37 mg, 0.17 mmol), followed by sodium tert-butoxide (48 mg, 0.50 mmol). The reaction mixture was stirred at 70 C for 16 h, and then filtered. The filtrate was concentrated and purified by flash chromatography using a 15 min gradient from 0 to 100% EtOAc in hexanes to give Intermediate 10B (70 mg, 0.16 mmol, 96% yield). LC-MS (ESI) m/z 440.1 (M+H), RT = 2.27 min (Method B).

References: [1]Patent: WO2013/151923,2013,A1 .Location in patent: Paragraph 00187.

12
[ 552846-17-0 ]
[ 1187932-25-7 ]
[ 1466528-30-2 ]