55186-89-5|1-Benzyl-1,4-diazepan-5-one| Ambeed

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Quality Control of [ 55186-89-5 ] Purity: 98% SDS Specification

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Product Details of [ 55186-89-5 ]

CAS No. :	55186-89-5
Formula :	C₁₂H₁₆N₂O
M.W :	204.27
SMILES Code :	C2=C(CN1CCC(=O)NCC1)C=CC=C2
MDL No. :	MFCD00225259
InChI Key :	DKNOPZCYIDBMNY-UHFFFAOYSA-N
Pubchem ID :	239726

Safety of [ 55186-89-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 55186-89-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	67.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	32.34 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.08
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	0.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.1
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.	1.18
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	1.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.76
Solubility	3.53 mg/ml ; 0.0173 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.04
Solubility	18.6 mg/ml ; 0.0913 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-3.47
Solubility	0.0689 mg/ml ; 0.000337 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	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	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	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.	-6.99 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	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)	1.49

Application In Synthesis of [ 55186-89-5 ]

* 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 [ 55186-89-5 ]

[ 55186-89-5 ] Synthesis Path-Downstream 1~27

1
[ 55186-89-5 ]
[ 4410-12-2 ]

References: [1]Journal of Organic Chemistry,1954,vol. 19,p. 1855,1856, 1859.

2
[ 3612-20-2 ]
[ 55186-89-5 ]

Yield	Reaction Conditions	Operation in experiment
47%		[Referential Example 119]; 1-Benzylhexahydro-1H-1,4-diazepin-5-one ; [] Concentrated sulfuric acid (25 mL) was added to 1-benzyl-4-piperidone (10.14 g) in acetic acid (50 mL) at room temperature, and sodium azide (3.880 g) was added thereto at 0C over a period of 2 hours, followed by stirring at 5C for 25 hours. The reaction mixture was alkalinized through addition of aqueous sodium hydroxide, followed by partitioning by use of chloroform. The aqueous layer was extracted with chloroform. The organic layers were combined, and washed with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and then the residue was purified through silica gel column chromatography (chloroform - methanol), to thereby give the title compound as a solid (5.081 g, 47%).1H-NMR(400MHz,CDCl3)delta: 2.50-2.70(6H,m), 3.20-3.35(2H,m), 3.60(2H,s), 6.07(1H,br), 7.20-7.40(5H,m). MS(ESI)m/z: 205(M+H)+.

References: [1]Patent: EP1591443,2005,A1 .Location in patent: Page/Page column 72.
[2]Tetrahedron Letters,1991,vol. 32,p. 2469 - 2470.
[3]Patent: WO2012/101654,2012,A2 .
[4]Patent: WO2014/16849,2014,A2 .

3
[ 949-69-9 ]
[ 55186-89-5 ]

Yield	Reaction Conditions	Operation in experiment
30%		Step 2: Synthesis of l-benzyl-l,4-diazepan-5-one [142]To a clean and dried two necked round bottom flask [141] (2 g, 0.00976 mol) was dissolved in acetone (20 ml) and acetonitrile (20 ml). The reaction mixture was cooled to 0 C, and then to it 15 % aqueous NaOH ( 1.2 ml) was added drop wise, followed by the addition of benzene sulphonyl chloride (1.49 ml, 0.01 1 mol). The reaction mixture was refluxed overnight. TLC showed complete consumption of SM. The reaction mixture was diluted with acetone, and passed through celite and concentrated. Saturated NaHC03 (50 ml) was added to the solid followed by extraction with EtOAc (3 X 150 ml), removal of the solvent under reduced pressure. The residue was purified by column chromatograph on silica gel with MeOH:DCM (1%) as an eluent to afford [142] as a white solid (600 mg, 30 %).ESIMS: 205 (M+ + 1)
30%	With benzenesulfonyl chloride; sodium hydroxide; In water; acetone; acetonitrile; at 0℃;Reflux;	Step 2 To a clean and dried two necked round bottom flask [110] (2 g, 9.76 mmol) was dissolved in acetone (20 ml) and acetonitrile (20 ml). The reaction mixture was cooled to 0 (>C, and then to it 15 % aqueous NaOH ( 1.2 ml) was added drop wise, followed by the addition of benzene sulphonyl chloride ( 1.49 ml, 1 1 mmol). The reaction mixture was refluxed overnight. TLC showed complete consumption of SM. The reaction mixture was diluted with acetone, and passed through celite and concentrated. Saturated NaHCOj (50 ml) was added to the solid followed by extraction with EtOAc (3 X 150 ml), removal of the solvent under reduced pressure. The residue was purified by column chromatography on silica gel with MeOH: DCM ( 1 ) as an eluent to afford [111] as a white solid (600 mg, 30 ). , ESIMS: 205 (M+ + 1 )

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 5832 - 5835.
[2]Patent: WO2012/101654,2012,A2 .Location in patent: Page/Page column 73.
[3]Patent: WO2014/16849,2014,A2 .Location in patent: Page/Page column 124.

5
[ 55186-89-5 ]
[ 623-48-3 ]
[ 214911-30-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 723 - 728.

6
[ 55186-89-5 ]
[ 34376-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen;palladium(II) hydroxide; In methanol; at 45℃;Inert atmosphere;	Step 3: Synthesis of l,4-diazepan-5-one [143]To a clean and dried two-necked RB flask taken compound [142] (600 mg, 2.93 mmol) was dissolved in eOH (15 ml). Concentrated HC1 (0.05 ml) and Pd(OH)2 ( 120 mg) were added sequentially under a nitrogen atmosphere. The reaction mixture was heated to 45 C under a hydrogen atmosphere and maintained at 45 C overnight. The reaction was monitored by mass analysis. Crude compound [143] obtained was used as such for the next step (350 mg, crude). ESIMS: 1 15 (M+ + 1 )
	With hydrogenchloride; hydrogen; palladium(II) hydroxide; In methanol; at 45℃;Inert atmosphere;	Step 3 To a clean and dried two-necked RB flask taken compound [111] (600 mg, 2.93 mmol) was dissolved in MeOH (15 ml). Concentrated HCI (0.05 ml) and Pd(OH)2 ( 120 mg) were added to the solution sequentially under a nitrogen atmosphere. The reaction mixture was heated to 45 C under a hydrogen atmosphere and maintained at 45 C overnight. The reaction was monitored by mass analysis. Crude compound [112] obtained was used as such for the next step (350 mg, crude). ESIMS: 1 15 (M+ + 1 )

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5907 - 5911.
[2]Patent: WO2012/101654,2012,A2 .Location in patent: Page/Page column 73-74.
[3]Patent: WO2014/16849,2014,A2 .Location in patent: Page/Page column 124; 125.

7
[ 55186-89-5 ]
[ 190900-21-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5907 - 5911.

8
[ 55186-89-5 ]
[ 214911-31-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 723 - 728.

9
[ 55186-89-5 ]
[ 214911-33-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 723 - 728.

10
[ 55186-89-5 ]
[ 214911-32-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 723 - 728.

11
[ 55186-89-5 ]
<i>N</i>-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-2-(7-oxo-4-phenylmethanesulfonyl-[1,4]diazepan-1-yl)-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 723 - 728.

12
[ 55186-89-5 ]
[ 214911-34-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 723 - 728.

13
[ 55186-89-5 ]
[ 190900-20-0 ]

References: [1]Patent: US6372733,2002,B1 .Location in patent: Example 1.

14
[ 39856-50-3 ]
[ 55186-89-5 ]
C₁₇H₁₈N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 100℃; for 12.0h;	To a solution of 24.6 mmol of 9 and 27.3 mmol of 7 in 50 mL of 1,4-dioxane was added 4.92 mmol of copper (I) iodide followed by the addition of 49.2 mmol of K3P04 and 4.92 mmol of trans-cyclohexanediamine, then the resulting mixture was stirred at 100C for 12 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with CHC13, poured into water, and insoluble material was removed by celite filtration. The filtrate was extracted with CHC13, dried over MgS04 and concentrated in vacuo. The crude product was purified by column chromatography to give 7.87 mmol of nitro derivative. [0202] A solution of 7.66 mmol of nitro derivative and 0.5 g of Pd/C (10%) in 150 mL of methanol was stirred overnight under H2 (1 atm). After filtering through celite, the solution was concentrated under reduced pressure to give 4.75 mmol of 8.
	With potassium phosphate;copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 100℃; for 12.0h;	To a solution of 24.6 mmol of 9 and 27.3 mmol of 7 in 50 mL of 1,4-dioxane was added 4.92 mmol of copper (I) iodide followed by the addition of 49.2 mmol ofK3P04 and 4.92 mmol of trans-cyclohexanediamine, then the resulting mixture was stirred at 100C for 12 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with CHC13, poured into water, and insoluble material was removed by celite filtration. The filtrate was extracted with CHCl3, dried over MgS04 and concentrated in vacuo. The crude product was purified by column chromatography to give 7.87 mmol of nitro derivative. [0233] A solution of 7.66 mmol of nitro derivative and 0.5 g of Pd/C (10%) in 150 mL of methanol was stirred overnight under H2 (1 atm). After filtering through celite, the solution was concentrated under reduced pressure to give 4.75 mmol of 8. ¹H NMR (400 MHz, DMSO-d6) 8 7.70 (d, J = 2.4 Hz, 1H), 7.17 (dd, J1 = 8.8 Hz, J2 = 2.4 Hz, 1H), 7.30-7.36 (m, 5H), 6.40 (d, J = 8.8 Hz, 1H), 5.90 (br s, 2H), 3.66-3.72 (m, 2H), 3.59 (br s, 2H), 2.59-2.71 (m, 6H); MS m/z: 327 (M+I).
	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 100℃; for 12.0h;	Example 6 Preparation of 8 6.1 Ullmann Cross-Coupling To a solution of 24.6 mmol of 9 and 27.3 mmol of 7 in 50 mL of 1,4-dioxane was added 4.92 mmol of copper (I) iodide followed by the addition of 49.2 mmol of K3PO4 and 4.92 mmol of trans-cyclohexanediamine, then the resulting mixture was stirred at 100 C. for 12 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with CHCl3, poured into water, and insoluble material was removed by celite filtration. The filtrate was extracted with CHCl3, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography to give 7.87 mmol of nitro derivative. A solution of 7.66 mmol of nitro derivative and 0.5 g of Pd/C (10%) in 150 mL of methanol was stirred overnight under H2 (1 atm). After filtering through celite, the solution was concentrated under reduced pressure to give 4.75 mmol of 8.

References: [1]Patent: WO2005/99711,2005,A1 .Location in patent: Page/Page column 22; 41.
[2]Patent: WO2005/100349,2005,A2 .Location in patent: Page/Page column 49.
[3]Patent: US2005/239800,2005,A1 .Location in patent: Page/Page column 10; 18.

15
[ 55186-89-5 ]
hexahydro-[1,4]diazepin-5-one; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In methanol; ethanol; at 20℃; for 4.0h;	Referential Example 120]; Hexahydro-1H-1,4-diazepin-5-one hydrochloride ; [] 1M HCl in ethanol (7.2 mL) and 10% palladium-carbon (0.34 g) were added to <strong>[55186-89-5]1-benzylhexahydro-1H-1,4-diazepin-5-one</strong> (1.490 g) in methanol (10 mL) at room temperature, and the resultant mixture was stirred in a hydrogen atmosphere for 4 hours. After the reaction atmosphere was purged with nitrogen, insoluble matter was removed by filtration. The solvent of the filtrate was evaporated under reduced pressure, and diethyl ether was added to the residue, and then the precipitated solid was recovered by filtration, to thereby give the title compound (1.045 g, 96%).1H-NMR(400MHz,CD3OD)delta: 2.75-2.85(2H,m), 3.25-3.40(6H,m), 3.48-3.56(2H,m) . MS(ESI)m/z: 115(M+H)+.

References: [1]Patent: EP1591443,2005,A1 .Location in patent: Page/Page column 72.

16
[ 55186-89-5 ]
[ 589-87-7 ]
[ 161265-03-8 ]
[ 477740-02-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With caesium carbonate;palladium diacetate; In 1,4-dioxane;	Part A. 1-Benzyl-4-(4-bromo-phenyl)-[1,4]diazepan-5-one: Commercially available <strong>[55186-89-5]1-benzyl-(1,4)-diazepan-5-one</strong> (14.7 mmol), p-bromoiodobenzene (1 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.15 eq), cesium carbonate (1.5 eq), and palladium acetate (0.1 eq) were placed in a round bottom flask and it was evacuated and flushed 3* with nitrogen. To this mixture was then added 200 mL of dioxane and the resulting solution was again evacuated and flushed 3* times with nitrogen gas. The mixture was allowed to stir at 75 C. overnight during which time the mixture turned from brown to bright yellow suspension. The mixture was cooled and diluted with dichloromethane and then was filtered through a pad of celite. The filtrate was removed under reduced pressure and the residue was purified by flash column chromatography eluding with 50% EtOAc/Hex to give compound 1 as an off-white solid (63%). Mass spectrum, ESI (M+H) 359.3, 361.3.

References: [1]Patent: US2002/183324,2002,A1 .

17
[ 55186-89-5 ]
1-benzyl-5,5-dideutero-1,4-diazepane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium deuteride; In tetrahydrofuran; at 20℃; for 24.0h;	1-Benzyl-1,4-diazepan-5-one (2.00 g, 9.79 mmol) was dissolved in THF (40 mL), LiAlD4 (9.80 mL, 2.0 M in THF, 19.6 mmol) was added dropwise over 5 min and the reaction mixture was stirred for 24 h. The reaction mixture was quenched with sat aq NaHCO3, filtered and concentrated in vacuo to give the crude title compound (1.80 g, 96%) as a pale yellow gum.

References: [1]Patent: US2013/289020,2013,A1 .Location in patent: Paragraph 0217; 0218.

18
[ 55186-89-5 ]
6-(4-benzyl-7,7-dideutero-1,4-diazepan-1-yl)-N-(pyridin-4-yl)pyridine-2-carboxamide [ No CAS ]