198480-21-6|1-(4-(2-(Azepan-1-yl)ethoxy)benzyl)-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole| Ambeed

Structure of 198480-21-6

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Quality Control of [ 198480-21-6 ] Purity: 97% SDS Specification

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Product Details of [ 198480-21-6 ]

CAS No. :	198480-21-6
Formula :	C₄₄H₄₆N₂O₃
M.W :	650.85
SMILES Code :	CC1=C(C2=CC=C(OCC3=CC=CC=C3)C=C2)N(CC4=CC=C(OCCN5CCCCCC5)C=C4)C6=C1C=C(OCC7=CC=CC=C7)C=C6
MDL No. :	MFCD09833278
InChI Key :	NXAHBBRIVLXMQA-UHFFFAOYSA-N
Pubchem ID :	9895831

Safety of [ 198480-21-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Computational Chemistry of [ 198480-21-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	49
Num. arom. heavy atoms	33
Fraction Csp3	0.27
Num. rotatable bonds	13
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	204.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	5.72
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	9.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	9.39
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.	5.73
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	9.55
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	8.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-9.66
Solubility	0.000000141 mg/ml ; 0.0000000002 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-10.43
Solubility	0.0000000241 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble
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	-14.79
Solubility	0.0 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
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.	-3.34 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	2.0
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	1.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
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	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.17

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<3.0
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)	4.64

Application In Synthesis of [ 198480-21-6 ]

* 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 [ 198480-21-6 ]

[ 198480-21-6 ] Synthesis Path-Downstream 1~35

1
[ 111-49-9 ]
[ 198480-07-8 ]
[ 198480-21-6 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1654 - 1657.

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[ 198480-21-6 ]
[ 198481-32-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium on activated charcoal; hydrogen; sodium hydroxide; In ethanol; ethyl acetate;	Add in 2000mL single-necked bottle1- (4- (2- (Acheptan-1-yl) ethoxy) benzyl) -5- (benzyloxy) -2- (4- (benzyloxy) phenyl) -3- Methyl-1H-indole175.0g, dissolved with 1400mL of ethyl acetate and ethanol mixture, then added 5ml of 1.0mol / L sodium hydroxide, and then added 52.5g of palladium on carbon,Fully reacted under hydrogen, after TLC detected the reaction,Filter to remove the catalyst palladium carbon, and then add a certain amount of L-ascorbic acid to the filtrate,Remove the solvent under reduced pressure and dry,That is, 126 g of bazedoxifene free base was obtained with a yield of 100%.
99%	With hydrogen;2.34% Pd/C; In tetrahydrofuran; ethanol; for 5h;	Example 8; Preparation of 1-[4-(2-azepan-1-yl-ethoxy)benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol (bazedoxifene); The starting compound, benzylated bazedoxifene of formula 7 (4.8 g; 7.38 mmol) was dissolved in an ethanol/THF mixture (1:1) (80 ml) and the catalyst, 2.34%-Pd/C (0.4 g) was added in an inert atmosphere. Then, the reaction mixture was stirred in the hydrogen atmosphere for 5 hours. The catalyst was filtered off through a celite layer in an inert atmosphere. The obtained clear, colourless filtrate was concentrated until dry.3.43 g (99%) of the bazedoxifene base were obtained in the form of off-white, solid foam. HPLC content 98.8%.
~ 99.72%	With hydrogen;palladium 10% on activated carbon; In methanol; water; acetone; at 40℃; under 7355.72 Torr;Product distribution / selectivity;	A mixture of 1 -(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(benzyloxy)-2-(4- benzyloxy)phenyl)-3-methyl-1 H-indole (10 g), acetone (150 mL) and methanol (100 mL), 10% palladium on carbon (2 g), and water (4 mL) is stirred under 10 Kg/cm2 hydrogen pressure at 40C until completion of the reaction, as verified using TLC. The mixture is cooled and filtered and the solid is washed with acetone (20 mL). The filtrate is distilled completely under vacuum, to afford bazedoxifene free base (7.1 g) in -99.72% yield.

97%	With hydrogen;palladium-on-charcoal; In ethyl acetate; at 30 - 35℃; under 2942.29 - 3677.86 Torr;	Example 17 Preparation of Bazedoxifene Free Base (Formula-9) The compound 8 from example 14 (17 g, 26 mmol) was dissolved in 340 ml of ethyl acetate and was subjected to catalytic hydrogenation with 5.1 g of 10% Pd/C, 50% wet, at a pressure of 4 to 5 kg/cm2 at 30-35 C. until completion of the reaction (6-7 hrs) as verified by TLC. The mixture was filtered and washed with ethyl acetate (50 ml). The filtrate was distilled completely under vacuum to afford a white foamy solid. Heptane (100 ml) was added to the solid and stirred for 30 min, filtered, washed with heptane (25 ml) and dried under vacuum to get title compound 9 (11.9 g, 97%) M.R: 170-174 C.; HPLC: 99.8% with the C-alkylated impurity below detection limits.
96.1%	With boron trifluoride diethyl etherate; In dichloromethane; ethanethiol; at 0 - 25℃; for 4h;	A solution of 1-(4-(2-(azepine-1-yl)ethoxy)benzyl)-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole (Intermediate III) and dissolved in 100 mL of anhydrous dichloromethane solution.10 mL of ethanethiol was added,Down to 0 C,A solution of 20 mL of 1 M boron trifluoride-diethyl ether was added dropwise.Drop finished, rose to 25 C stirring 4h,TLC detection reaction is complete. Add 20mL of purified water to quench the reaction, filter and extract the filtrate. The organic layer was washed once with 50 mL of saturated brine and dried over anhydrous sodium sulfate. The organic layer was concentrated at 45 C under reduced pressure to give 6.95 g of a white solid, (Formula I), yield 96.1%, purity (HPLC) 99.53%
96.3%	With palladium 10% on activated carbon; ammonium formate; In water; ethyl acetate; at 70 - 80℃;	Step S21, 30.0 g of Compound A (45 mmol) was dissolved in 300 mL of ethyl acetate, wherein Compound A had the structure shown in Formula I below:In step S22, 3.0 g of palladium carbon (10%, 50% to 65% by weight) and 14.4 g of ammonium formate (229 mmol) are added under stirring to carry out a reaction, and the reaction temperature is controlled to be about 70 to 80 C, and the reaction time is 2 hours. 6 hours.In step S23, palladium carbon is filtered off, and the filtrate is washed successively with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and the organic phase is separated.Step S24, the organic phase is dried with anhydrous sodium sulfate, filtered, and the filtrate is concentrated under reduced pressure, the temperature is 40 C - 45 C, the degree of vacuum is ≤ -0.08 MPa, and 20.9 g of bazedoxifene free base is obtained.The yield was 96.3%.
89.2%	With formic acid; palladium on activated charcoal; ammonium formate; at 65℃; for 1h;Large scale;	A 1000-L reactor was charged with the prepared 360 kg EA (containing 5% by volume of MeOH).The temperature was raised to 65±5C, and 2.4 kg of formic acid was added, 40 kg of compound 5 prepared in Example 3 was stirred until dissolved, 10 kg of Pd/C and 16 kg of ammonium formate were added, and the reaction was incubated for 1 h. After the reaction, the silica gel column was used with 360 kg of EA. (containing 2% volume of methanol) elution, the filtrate was collected, concentrated under reduced pressure at 45C, then added with 160kg acetone for 1h and filtered.Drying yielded 25.8 kg of an off-white solid, yield 89.2%, HPLC purity: 99.8%.
	With hydrogen;palladium 10% on activated carbon; In ethanol; ethyl acetate; at 25℃; under 2585.81 Torr; for 20h;	A 2 gal hydrogenation vessel with agitator was charged with hexamethyleneimino benzyloxyindole (250 g, 0.3841 mols; see U. S. Pat. No. 5,998,402 for a preparation), ethanol (denatured with 5% by volume ethyl acetate) (1578 g, 2000 mL), and palladium on carbon 10% (25 g). The reactants were hydrogenated at 25 C and 50 psi for 20 hours. Reaction progress was monitored by HPLC (Column: CSC-S ODS 2,25 cm; Mobile phase: 20 % 0.02 M NH4H2P04 (2 mL TEA/L, pH = 3) and 80 % MeCN; Flow: 2 mL/min; Detector: 220 nm). The reaction was considered complete when less than 1% of either the hexamethyleneimino benzyloxyindole (18.2 min retention time) or mono- debenzylated derivative thereof (5.1 min retention time) was detected.
	With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; ethanol;	A solution consisting of indole 44 (17.5g, 26.9 mmol) in THF/EtOH (1:1) was hydrogenated under an atmosphere of H2 using 10% Pd/C as a catalyst. Chromatography on silica gel CH2Cl2/MeOH (gradient from 100/0 to 85/15) yields the desired product as 8.5 g of white foam along with 2.5 g of a fraction containing small impurities. Although the free base is the material used in the next step (bis-glucuronidation), for purposes of characterization and enhancing the compounds shelf life an acid addition salt may be made with HCl by dissolving the compound in MeOH and treating with 1.1 eq of a 2 N aq HCl solution. The compound slowly precipitates out as white crystals. Physical data listed below describes the HCl salt of indole 45: Mp = 172-174C; 1H NMR (DMSO) 10.11 (br s, 1 H), 9.70 (s, 1 H), 8.71 (s, 1 H); 7.15 (d, 2 H, J = 8.6 Hz), 7.05 (d, 1 H, J = 8.8 Hz), 6.85 (d, 2 H, J = 8.8 Hz), 6.80 - 6.77 (m, 5 H), 6.56 (dd, 1 H, J = 8.8 Hz, 2.2 Hz), 5.11 (s, 2 H), 4.26 (t, 2 H, J = 4.6 Hz), 3.48 - 3.30 (m, 4 H), 3.22 - 3.08 (m, 2 H), 2.09 (s, 3 H), 1.83 - 1.76 (m, 4 H), 1.67 - 1.48 (m, 4 H); IR (KBr) 3500 br, 3250 br, 2900, 1610; MS FAB m/z 471 (M+H+).
	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 45 - 50℃; under 7355.72 Torr; for 2h;	EXAMPLE 22: PREPARATION OF BAZEDOXIFENE FREE BASE. A mixture of 1 -(4-(2-(azepan-1 -yl)ethoxy)benzyl)-5-(benzyloxy)-2-(4- benzyloxy)phenyl)-3-methyl-1 H-indole (15 g) and ethyl acetate (150 mL) is heated to 40C to produce a clear solution, then 10% palladium on carbon (3 g) is added and the mixture is stirred under 10 Kg/cm2 hydrogen pressure at 45-50C until completion of the reaction (about 2 hours), as verified using TLC. The mixture is cooled to room temperature, filtered, and the collected solid washed with ethyl acetate (30 mL). The filtrate is used further treatments.
	With palladium 10% on activated carbon; hydrogen; sodium L-ascorbate; In tetrahydrofuran; ethanol; at 20℃; for 15h;Inert atmosphere;	See, generally, Miller et al., in I. Med.Chem. 2001, 44, 1654-1657. 1 -(4-(2-(Azepan- 1 -yl)ethoxy)benzyl)-5-(benzyloxy)-2-(4- benzyloxy)phenyl)-3-methyl-1H-indole (8A) (2.0 g, 3.07 mmol) is dissolved in tetrahydrofuran (100 mL) in a 500 mL round bottom flask with a stirring bar and sodium ascorbate (100 mg) is added followed by ethanol (100 mL). The flask is blanketed with argon, 10% Pd/C (200 mg) is added and the flask is covered with a rubber septum. The reaction mixture is blanketed with hydrogen (balloon) and stirred for 15 h at ambient temperature. TLC (CH2C12:MeOH 9:1) shows the disappearance of 8A, Rf -0.6 and a single new spot (Rf -0.1, LCMS retention time8.6 mi mle 471). The hydrogenation reaction is filtered through a Celite pad, washed with ethanol (25 mL) and the filtrate is evaporated to a colorless oil. The oil is dissolved in acetone (30 mL) and heated to 35C with stuffing. Seed crystals of bazedoxifene acetate (9) are added to the solution and glacial acetic acid (200 mg, 3.3 mmol) in acetone (1 mL) is slowly added. The solution is allowed to cool to room temp slowly resulting in white crystals. Stuffing iscontinued for 1 hr and the crystals are collected by filtration, washed with cold acetone (-15C)and dried in a vacuum at 40C for 1 hr, (1.4 g, 97%). LCMS retention time 7.95 mm (100 %)mle 471; mp 168-169C (Lit mp 170.5-172.5C), NMR (DMSO-d6) 11.89 (br s, 1H), 9.67 (brs, 1H), 8.68 (br s, 1H), 7.15 (d, 2H, I = 8.5 Hz). 7.06 (d, 1H, I = 8.7 Hz), 6.85 (d, 2H, I = 8.5Hz), 6.80 (d, 1H, 1 =2.3Hz), 6.75 (d, 2H, 1 =9.0 Hz), 6.74 (d, 2H, I = 9.0 Hz), 6.57 (dd, 1H, I =8.7 Hz, 2.3 Hz), 5.10 (s, 2H), 3.93 (t, 2H, I = 6.1 Hz), 2.77 (t, 2H, I = 6.1 Hz), 2.63 (m, 4H),2.10 (s, 3H), 1.91 (s, 3H), 1.47-1.58 (m, 8H).
	With hydrogen;palladium on activated charcoal; In ethanol; ethyl acetate; at 50℃; under 1500.15 - 3000.3 Torr;	Example 4Preparation of Bazedoxifene Acetate[0055] A hydrogenation vessel is charged with hexamethyleniminobenzyloxy indole(64.4 Kg), ethyl acetate (95.7 Kg, 106.3 L), ethyl alcohol (244.6 Kg, 309.7 L) and palladium/C5 (2.5% p/p, 2.54 Kg) under nitrogen. The vessel is degassed with hydrogen and then is recharged with hydrogen up to the pressure of 2 bar. The reaction mixture is heated to about 50 +/- 2C, and the hydrogen pressure is finally set at 4 bar. After about 2 hours from the end of the hydrogen absorption, the vessel is degassed up to 0.1 bar and an HPLC analysis of the reaction mixture is performed to ensure that the reaction is complete. After a positive response of the analysis, the mixture is cooled to about 20-30C, and the vessel is degassed with nitrogen. Then the vessel is charged with ascorbic acid (0.50 Kg) and the <n="15"/>internal temperature is set at about 40-50C. The solution is stirred at about 40-50C for about 20 min..

References: [1]Patent: CN111004165,2020,A .Location in patent: Paragraph 0028-0031; 0044-0046.
[2]Patent: US2010/240888,2010,A1 .Location in patent: Page/Page column 5.
[3]Patent: WO2011/22596,2011,A2 .Location in patent: Page/Page column 29.
[4]Patent: US2012/330008,2012,A1 .Location in patent: Page/Page column 10.
[5]Patent: CN106810487,2017,A .Location in patent: Paragraph 0078-0080; 0090-0091; 0100; 0107; 0114; 0121; 0126.
[6]Patent: CN109851547,2019,A .Location in patent: Paragraph 0055-0060; 0075-0080; 0093-0098; 0102-0107.
[7]Chemico-Biological Interactions,2012,vol. 197,p. 8 - 15.
[8]Patent: CN107793344,2018,A .Location in patent: Paragraph 0016; 0025; 0060-0064.
[9]Journal of Medicinal Chemistry,2001,vol. 44,p. 1654 - 1657.
[10]Patent: WO2005/100314,2005,A1 .Location in patent: Page/Page column 15-16.
[11]Patent: EP1212335,2006,B1 .Location in patent: Page/Page column 23.
[12]Patent: WO2012/37187,2012,A2 .Location in patent: Page/Page column 23.
[13]Patent: WO2014/186325,2014,A1 .Location in patent: Page/Page column 25; 28; 29.
[14]Patent: WO2009/102773,2009,A1 .Location in patent: Page/Page column 13-14.

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[ 198480-21-6 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1654 - 1657.
[2]Patent: WO2011/22596,2011,A2 .
[3]Chemico-Biological Interactions,2012,vol. 197,p. 8 - 15.

4
[ 35081-45-9 ]
[ 198480-21-6 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1654 - 1657.
[2]Patent: WO2011/22596,2011,A2 .
[3]Chemico-Biological Interactions,2012,vol. 197,p. 8 - 15.
[4]Patent: CN106810487,2017,A .
[5]Patent: US2019/389842,2019,A1 .
[6]Patent: CN113816892,2021,A .

5
[ 51388-20-6 ]
[ 198480-21-6 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1654 - 1657.
[2]Patent: WO2011/22596,2011,A2 .
[3]Patent: CN106810487,2017,A .

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[ 198480-21-6 ]