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Quality Control of [ 20637-09-6 ] Purity: 97% SDS Specification

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Product Details of [ 20637-09-6 ]

CAS No. :	20637-09-6
Formula :	C₁₁H₁₅NO₂
M.W :	193.24
SMILES Code :	O=C(OC)CCCC1=CC=C(N)C=C1
MDL No. :	MFCD07366753
InChI Key :	CLKHQWJXESOLCJ-UHFFFAOYSA-N
Pubchem ID :	88628

Safety of [ 20637-09-6 ]

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

Calculated chemistry of [ 20637-09-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	5
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	56.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.12
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	2.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.77
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.	1.96
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	2.04
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.0

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.34
Solubility	0.879 mg/ml ; 0.00455 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.	-2.82
Solubility	0.293 mg/ml ; 0.00152 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	-3.33
Solubility	0.09 mg/ml ; 0.000466 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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.	-5.99 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	1.0
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.	1.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 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)	1.28

Application In Synthesis of [ 20637-09-6 ]

* 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 [ 20637-09-6 ]

[ 20637-09-6 ] Synthesis Path-Downstream 1~29

1
[ 75-21-8 ]
[ 20637-09-6 ]
[ 305-03-3 ]

References: [1]Journal of the Chemical Society,1953,p. 2386,2387.

2
[ 20637-02-9 ]
[ 20637-09-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen;palladium on activated charcoal; In methanol; for 3h;	b) Methyl 4-(4-aminophenyl)butanoateA suspension of methyl 4-(4-nitrophenyl)butanoate (3.05 g, 13.67 mmol) and Pd/C (1.0 g, 10percent Pd on activated C, 1.09 mmol) in MeOH (40 ml_) was stirred under H2 atmosphere (balloon) for 3 h. The reaction mixture was filtered through Celite (washing with EtOAc). Solvent was concentrated off, to furnish 2.33 g of methyl 4-(4-aminophenyl)butanoate (brown solid, yield: 88percent). It was submitted to next step without purification.1H NMR (CDCI3, 250 MHz) delta ppm: 6.96 (d, J = 8.5 Hz, 2H), 6.63 (d, J = 8.2 Hz, 2H), 3.66 (s, 3H), 2.55 (t, J = 7.6 Hz, 2H), 2.31 (t, J = 7.7 Hz, 2H), 1.90 (q, J = 7.6 Hz, 2H).

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6463 - 6480.
[2]Patent: WO2009/80722,2009,A2 .Location in patent: Page/Page column 52.
[3]Journal of Pharmaceutical Sciences,1988,vol. 77,p. 185 - 187.
[4]Journal of the Chemical Society,1953,p. 2386,2387.
[5]Journal of Medicinal Chemistry,1990,vol. 33,p. 3014 - 3019.
[6]Journal of Pharmaceutical Sciences,1980,vol. 69,p. 80 - 84.

3
[ 20637-09-6 ]
[ 75-56-9 ]
[ 55774-31-7 ]

References: [1]Journal of the Chemical Society,1953,p. 2386,2387.

4
[ 20637-09-6 ]
[ 544-92-3 ]
[ 20637-03-0 ]

References: [1]Journal of the Chemical Society B: Physical Organic,1969,p. 439 - 445.

5
[ 75-21-8 ]
[ 20637-09-6 ]
[ 130198-76-4 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3014 - 3019.
[2]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5007 - 5012.

6
[ 1943-83-5 ]
[ 20637-09-6 ]
[ 113849-33-5 ]

References: [1]Journal of Pharmaceutical Sciences,1988,vol. 77,p. 185 - 187.

7
[ 20637-09-6 ]
[ 55661-43-3 ]
methyl 4-3-nitroso>ureido>phenyl>butyrate [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1988,vol. 77,p. 185 - 187.

8
[ 20637-09-6 ]
[ 1208-03-3 ]
4-<γ-(methoxycarbonyl)propyl>-N-<p-<bis-(β'-chlorethyl)amino>>benzylideneaniline [ No CAS ]

References: [1]Bulletin des Societes Chimiques Belges,1988,vol. 97,p. 941 - 944.

9
[ 20637-09-6 ]
[ 624-65-7 ]
[ 101248-43-5 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1114 - 1118.

10
[ 6552-57-4 ]
[ 20637-09-6 ]
C₁₅H₁₅⁽²⁾H₈NO₄ [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1980,vol. 69,p. 80 - 84.

11
[ 198544-23-9 ]
[ 20637-09-6 ]

References: [1]Journal of Fluorine Chemistry,1997,vol. 84,p. 119 - 126.

Yield	Reaction Conditions	Operation in experiment
		The material so obtained was dissolved in a mixture of methanol (200 ml) and water (100 ml) and heated to reflux on a steam bath. Ferrous sulphate heptahydrate (11.71 g) and iron powder (34.0 g) were added and the mixture was heated to reflux for 6 hours. The solution was filtered whilst hot. Methanol was evaporated from the filtrate and the residual aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried and evaporated to give a residue which was purified by column chromatography on silica gel using methylene chloride as eluent. There was thus obtained methyl 4-(4-aminophenyl)butyrate (6.22 g).

14
[ 20637-09-6 ]
[ 330955-07-2 ]
4-{4-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-phenyl}-butyric acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 151 - 155.

15
[ 67-56-1 ]
[ 15118-60-2 ]
[ 20637-09-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sulfuric acid; for 1.5h;Reflux;	A 250-mL round bottom flask was charged with 4-(4-aminophenyl)butyric acid (2.00 g, 11.2 mmol) in methanol (50 mL) and treated with cone, sulfuric acid (1 mL). The resultant mixture was heated to reflux for 1.5 h. After this time, methanol (-25 mL) was distilled off. The reaction was cooled to 60 °C and methyl tert-butyl ether was added. The mixture was allowed to slowly cool to room temperature, then diluted with hexanes (50 mL) to afford a white solid. The solid was dissolved in THF (6 mL)/water (4 mL) and treated with cone. NH4OH (6 mL). The mixture was diluted with dichloromethane (50 mL) and the layers separated. The organic layer was washed with saturated sodium chloride (5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (2.07 g, 96percent) as a brown solid. MW = 193.24. ]H NMR (DMSO-i, 500 MHz) delta 6.83-6.79 (m, 2H), 6.50-6.46 (m, 2H), 4.81 (s, 2H), 3.57 (s, 3H), 2.39 (t, J = 7.5 Hz, 2H), 2.25 (t, 7 = 7.5 Hz, 2H), 1.73 (quin, / = 7.5 Hz, 2H).
70%	With thionyl chloride; In methanol; at 0 - 80℃; for 16h;	Synthesis of cyanoamine 28Preparation of methyl 4-(4-aminophenyl)butanoate 27.[00200] To a mixture of compound 26 (0.92 g, 5.13 mmol) in CH30H (20 mL) was added dropwise thionyl chloride (1.9 mL , 25.7 mmol) at OoC with stirring. After addition, the reaction mixture was stirred at 80 oC for 16 h, concentrated in vacuo. The residue was diluted with aqNaHC03, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04 and concentrated to dryness to give compound 27 (0.7 g, 70percent) as a light yellow solid. 1H NMR (400 MHz, CDC13) 56.97 (d, 2H, J=8.3 Hz), 6.64 (d, 2H, J=8.3 Hz), 3.68 (br s, 2H), 3.66(s, 3H), 2.54 (t, 2H, J=7.4 Hz), 2.3 l(t, 2H, J=7.4 Hz), 1.85- 1.95(m, 2H).

References: [1]Patent: WO2014/66659,2014,A1 .Location in patent: Paragraph 0722.
[2]Patent: WO2012/119559,2012,A1 .Location in patent: Page/Page column 85.
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1784 - 1789.
[4]Bioorganic and medicinal chemistry letters,2001,vol. 11,p. 2847 - 2850.

16
[ 20637-09-6 ]
[ 98-09-9 ]
4-(4-benzenesulfonylamino-phenyl)-butyric acid methyl ester [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2001,vol. 11,p. 2847 - 2850.

17
[ 20637-09-6 ]
[ 418771-11-6 ]
4-{4-[2-((3aR,4S,5aR,9aR,9bR)-2,2,8,8-Tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)-acetylamino]-phenyl}-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1563 - 1566.

18
[ 54299-16-0 ]
[ 20637-09-6 ]
methyl 4-{4-[bis(2-hydroxy-[1,2-14C]ethyl)amino]phenyl}butyrate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5007 - 5012.

19
[ 20637-09-6 ]
[ 22921-68-2 ]
[ 852068-07-6 ]