184031-16-1|tert-Butyl 1H-indol-5-ylcarbamate| Ambeed

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Quality Control of [ 184031-16-1 ] Purity: 97% SDS Specification

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Product Details of [ 184031-16-1 ]

CAS No. :	184031-16-1
Formula :	C₁₃H₁₆N₂O₂
M.W :	232.28
SMILES Code :	CC(C)(C)OC(=O)NC1=CC2=C(NC=C2)C=C1
MDL No. :	MFCD04114771
InChI Key :	VGVLKMYJBZYCIS-UHFFFAOYSA-N
Pubchem ID :	11458923

Safety of [ 184031-16-1 ]

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

Computational Chemistry of [ 184031-16-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	9
Fraction Csp3	0.31
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	68.54
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.39
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	1.95
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.32
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.	1.78
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	2.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.35

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.64
Solubility	0.537 mg/ml ; 0.00231 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.	-2.71
Solubility	0.452 mg/ml ; 0.00194 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-4.24
Solubility	0.0133 mg/ml ; 0.0000573 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	Yes
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	No
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.	-6.33 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)	2.15

Application In Synthesis of [ 184031-16-1 ]

* 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 [ 184031-16-1 ]

[ 184031-16-1 ] Synthesis Path-Downstream 1~31

1
[ 5192-03-0 ]
[ 24424-99-5 ]
[ 184031-16-1 ]

Yield	Reaction Conditions	Operation in experiment
> 100%	In ethyl acetate; at 20℃; for 24h;	To a solution 5-aminoindole (1.0 g, 7.6 mmol) in 100 mL of EtOAc was added di- tert-butyldicarbonate (4.1 g. 19 mmol). The mixture was stirred at ambient temperature for 24 hours and then was quenched with 20 mL H2O. The layers were separated and the aqueous layer was extracted 3 X 10 mL of EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 50% hexanes in EtOAc) to provide the title compound (1.8 g, 7.7 mmol, ->100% yield). MS (DCI/NH3) m/z 233 (M+H)+.
94%	With triethylamine; In methanol; at 20℃; for 6h;	Example 16 (1-{4-[3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido]-2-fluorophenyl}-1H-indol-5-yl)carbamic acid tert-butyl ester (Table 1, Compound No. 16) Step A Preparation of (1H-indole-5-yl)carbamic acid tert-Butyl ester [Show Image] In 100 mL of methanol, 2.64 g (20 mmol) of 5-aminoindole was dissolved, and 4.15 mL (30 mmol) of triethylamine and 5.23 g (24 mmol) of Boc2O were added thereto and the mixture solution was stirred at room temperature for six hours. The reaction solution was concentrated under reduced pressure, and the residue was partitioned with ethyl acetate (200 mL) and water (100 mL), and the organic layer was washed with a saturated sodium chloride solution. The organic layer was dried and then concentrated under reduced pressure, and the residue was partitioned between ethyl acetate (200 mL) and water (100 mL) and the organic layer was washed with a saturated sodium chloride solution. The organic layer was dried and then concentrated under reduced pressure, and the residue was purified by a silica gel column (Wako Gel C200: 300 g, n-hexane:ethyl acetate=4:1) to obtain 4.38 g (94%) of (1H-indol-5-yl)carbamic acid tert-butyl ester as a white solid. 1H-NMR (270 MHz, CDCl3) δ (ppm): 1.43(9H,s), 6.38 (1H, br.s), 6.29-6.33 (1H, m), 7.04 (1H, dd, J=2.3, 8.9 Hz), 7.19 (1H, s), 7.23 (1H, d, J=8.9 Hz), 7.61 (1H, br.s)
43%	With triethylamine; In dichloromethane; at 0 - 20℃; for 4h;	Intermediate-69: tert-Butyl lH-indol-5-ylcarbamate To a stirred solution lH-indol-5 -amine (0.5 g, 3.78 mmol) in dichloromethane (10 mL), triethylamine (0.95g, 9.4 mmol) and di-tert-butyl dicarbonate (0.908 g, 4.166 mmol) were added at 0C. The reaction contents were stirred at room temperature for 4 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give tert-butyl lH-indol-5-ylcarbamate (0.380 g, 43%); MS: 233.5 (M+l).

In dichloromethane; at 20℃;

A solution of 5-amino indole (2 g, 15.2 mmol) and di-tert-butyl dicarbonate (3.49 g. 15.2 mmol) in dichloromethane (20 ml) was stirred at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure to yield crude (1H-indol-5-yl)-carbamic acid tert-butyl ester (3.47 g) which was used in the next step without further purification. MS: 250.3 (M+NH4)+.

References: [1]Patent: WO2006/69196,2006,A1 .Location in patent: Page/Page column 117.
[2]Journal of the American Chemical Society,2005,vol. 127,p. 4996 - 4997.
[3]Patent: EP1724258,2006,A1 .Location in patent: Page/Page column 69-70.
[4]Synlett,2004,p. 1794 - 1798.
[5]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.
[6]Patent: WO2012/69917,2012,A1 .Location in patent: Page/Page column 46-47.
[7]Patent: US2005/96353,2005,A1 .Location in patent: Page/Page column 23.
[8]Journal of Medicinal Chemistry,2008,vol. 51,p. 1904 - 1912.

2
[ 591-50-4 ]
[ 184031-16-1 ]
(2-phenyl-5-indolyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 4996 - 4997.

3
[ 78-94-4 ]
[ 184031-16-1 ]
tert-butyl 3-(3-oxobutyl)indole-5-carbamate [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 175 - 178.

4
[ 105-36-2 ]
[ 184031-16-1 ]
[ 851069-71-1 ]

Yield	Reaction Conditions	Operation in experiment
34%	With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃;	Cesium carbonate (7.17 g, 22 mmol) was added to a solution of 1H-indol-5-yl)-carbamic acid tert-butyl ester (3.39 g, 14.6 mmol) and bromo-acetic acid ethyl ester (2.38 ml, 20.3 mmol) in N,N-dimethyl formamide (30 ml). The reaction mixture was stirred at ambient temperature overnight, taken up in diethylether and washed with 1N HCl and water. The crude product was purified by chromatography over silica gel with AcOEt/heptane 1:3 to obtain (5-tert-butoxycarbonylamino-indol-1-yl)-acetic acid ethyl ester (1.6 g, 5.03 mmol, 34%). MS: 319.4 (M+H)+.

References: [1]Patent: US2005/96353,2005,A1 .Location in patent: Page/Page column 23.

5
[ 24303-61-5 ]
[ 184031-16-1 ]
[ 895157-62-7 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1904 - 1912.

6
[ 5888-29-9 ]
[ 184031-16-1 ]
[ 1228023-66-2 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 3923 - 3926.

7
[ 184031-16-1 ]
[ 1414628-64-0 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.

8
[ 184031-16-1 ]
[ 1414628-89-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.

9
[ 184031-16-1 ]
[ 1414628-97-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.

10
[ 184031-16-1 ]
[ 1414628-41-3 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.

11
[ 184031-16-1 ]
[ 1414628-82-2 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.

12
[ 184031-16-1 ]
[ 1414628-54-8 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.

13
[ 79-04-9 ]
[ 184031-16-1 ]
[ 1414627-92-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1040 - 1048.

14
[ 79-37-8 ]
[ 184031-16-1 ]
C₁₅H₁₅ClN₂O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10532 - 10539.

15
[ 184031-16-1 ]
[ 1549940-55-7 ]