[ CAS No. 2080-75-3 ] {[proInfo.proName]}

Name: 2080-75-3|5-Methoxy-1H-benzo[d]imidazol-2(3H)-one|95%
Brand: Ambeed
SKU: A120315
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Quality Control of [ 2080-75-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2080-75-3 ]

SDS Specification

Alternatived Products of [ 2080-75-3 ]

Product Details of [ 2080-75-3 ]

CAS No. :	2080-75-3	MDL No. :	MFCD01462048
Formula :	C₈H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AUPLVAKFTYFHTA-UHFFFAOYSA-N
M.W :	164.16	Pubchem ID :	591101
Synonyms :		Chemical Name :	5-Methoxy-1H-benzo[d]imidazol-2(3H)-one

Calculated chemistry of [ 2080-75-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.41
TPSA :	57.88 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.42
Log Po/w (XLOGP3) :	0.53
Log Po/w (WLOGP) :	0.86
Log Po/w (MLOGP) :	0.58
Log Po/w (SILICOS-IT) :	2.13
Consensus Log Po/w :	1.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.68
Solubility :	3.42 mg/ml ; 0.0209 mol/l
Class :	Very soluble
Log S (Ali) :	-1.32
Solubility :	7.92 mg/ml ; 0.0482 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.94
Solubility :	0.19 mg/ml ; 0.00116 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.45

Safety of [ 2080-75-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2080-75-3 ]

* 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.

Upstream synthesis route of [ 2080-75-3 ]
Downstream synthetic route of [ 2080-75-3 ]

[ 2080-75-3 ] Synthesis Path-Upstream 1~14

1
[ 213118-56-0 ]
[ 2080-75-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 5 h;	Intermediate 37:[0168] Intermediate 36 (7.3 g, 30.6 mmol) was dissolved in DMF (70 mL). To this solution was added anhydrous K₂C0₃ (4.7 g, 33.7 mmol) and the mixture was heated to reflux (130°C) for 5 h. The solvent was removed under pressure, the residue was poured into ice water, and the aq phase was extracted with EtOAc. The combined organic layers were dried over anhydrous Na₂S0₄, concentrated under vacuum, and the resulting yellow solid was recrystallized from EtOH to give 5-methoxy-lH-benzo[^imidazol-2(3H)-one (intermediate 37) (3.6 g, 72percent) as a yellow solid, mp: 249-251°C.

Reference： [1] Patent: WO2012/3418, 2012, A2, . Location in patent: Page/Page column 71

2
[ 32315-10-9 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 552 - 557

3
[ 623-49-4 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1] Letters in Organic Chemistry, 2011, vol. 8, # 6, p. 406 - 411

4
[ 124-38-9 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1] Chemistry - An Asian Journal, 2016, vol. 11, # 19, p. 2735 - 2740

5
[ 57-13-6 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1] MedChemComm, 2013, vol. 4, # 3, p. 527 - 529

6
[ 4887-80-3 ]
[ 2080-75-3 ]

Reference： [1] Chemistry of Natural Compounds, 1983, vol. 19, # 1, p. 124 - 125[2] Khimiya Prirodnykh Soedinenii, 1983, # 1, p. 121

7
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1] Patent: WO2012/3418, 2012, A2,
[2] Letters in Organic Chemistry, 2011, vol. 8, # 6, p. 406 - 411

8
[ 96-96-8 ]
[ 2080-75-3 ]

Reference： [1] Patent: WO2012/3418, 2012, A2,

9
[ 1329028-11-6 ]
[ 2080-75-3 ]

Reference： [1] Letters in Organic Chemistry, 2011, vol. 8, # 6, p. 406 - 411

10
[ 27185-61-1 ]
[ 2080-75-3 ]

Reference： [1] Chemistry - A European Journal, 2014, vol. 20, # 43, p. 13854 - 13859

11
[ 104-94-9 ]
[ 2080-75-3 ]

Reference： [1] Chemistry - A European Journal, 2014, vol. 20, # 43, p. 13854 - 13859

12
[ 1150-26-1 ]
[ 2080-75-3 ]

Reference： [1] Chemistry - A European Journal, 2014, vol. 20, # 43, p. 13854 - 13859

13
[ 3360-81-4 ]
[ 2080-75-3 ]

Reference： [1] Chemistry - A European Journal, 2014, vol. 20, # 43, p. 13854 - 13859

14
[ 530-62-1 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 719 - 723

[ 2080-75-3 ] Synthesis Path-Downstream 1~48

1
[ 2080-75-3 ]
[ 64107-38-6 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 1662

2
[ 4887-80-3 ]
[ 2080-75-3 ]

Reference： [1]Chemistry of Natural Compounds,1983,vol. 19,p. 124 - 125
Khimiya Prirodnykh Soedinenii,1983,p. 121

4
[ 2080-75-3 ]
diethyl-<2-halogen-ethyl>-amine [ No CAS ]
[ 113570-51-7 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 1662

5
[ 2080-75-3 ]
1-halogenepoxy propane [ No CAS ]
5-Methoxy-1,3-bis-oxiranylmethyl-1,3-dihydro-benzoimidazol-2-one [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1984,vol. 34,p. 663 - 668

6
[ 2080-75-3 ]
[ 15965-54-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 719 - 723
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5010 - 5014

7
[ 530-62-1 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 719 - 723

8
[ 2080-75-3 ]
2-[4-(3-chloro-pyridin-2-yl)-2-methyl-piperazin-1-yl]-5-methoxy-1<i>H</i>-benzoimidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 719 - 723

9
[ 2080-75-3 ]
[ 39513-24-1 ]

Yield	Reaction Conditions	Operation in experiment
80%		Intermediate 38:[0169] A mixture of intermediate 37 (3.6 g, 22 mmol) and 48% hydrogen iodide (30 mL) was heated to reflux (130C) and stirred for 12 h. The reaction mixture was neutralized to pH = 8 with aq NaOH and then extracted with EtOAc. The combined organic layers were dried over anhydrous Na2S04, concentrated under vacuum and purified by flash chromatography on silica gel column (elution with DCM/MeOH = 80: 1) to give 5-hydroxy-lH-benzo[cf]imidazol-2(3H)- one (intermediate 38) (16.9 g, 80%). HPLC: 99%, RT 1.377 min. MS (ESI) m/z 151.0 [M + H]+. mp: 186-187C
	With aluminum (III) chloride; In dichloromethane; nitrobenzene; at 20℃; for 96h;	To <strong>[2080-75-3]5-methoxy-1H-benzo[d]imidazol-2(3H)-one</strong> (164 mg, 1 mmol, Lancaster) in DCM (2 mL) was added 1 M solution of aluminium trichloride in nitrobenzene (1 mL, 1 mmol, Aldrich). The reaction mixture was stirred at room temperature for 4 days and evaporated in vacuo. The residue was filtered through Celite, and the filter cake was washed with DCM. The DCM washings were discarded and the filter cake was washed with MeOH. The dark brown MeOH washings were collected and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (gradient: 5-20% MeOH/CH2Cl2) to give the title compound as a pale-yellow solid. MS (ESI, pos. ion.) m/z: 151 (M+1).

Reference： [1]Patent: WO2012/3418,2012,A2 .Location in patent: Page/Page column 71
[2]Patent: US2005/176726,2005,A1 .Location in patent: Page/Page column 25
[3]MedChemComm,2013,vol. 4,p. 527 - 529

10
[ 96-96-8 ]
[ 2080-75-3 ]

Reference： [1]Patent: WO2012/3418,2012,A2

11
[ 213118-56-0 ]
[ 2080-75-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 5h;	Intermediate 37:[0168] Intermediate 36 (7.3 g, 30.6 mmol) was dissolved in DMF (70 mL). To this solution was added anhydrous K2C03 (4.7 g, 33.7 mmol) and the mixture was heated to reflux (130C) for 5 h. The solvent was removed under pressure, the residue was poured into ice water, and the aq phase was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2S04, concentrated under vacuum, and the resulting yellow solid was recrystallized from EtOH to give 5-methoxy-lH-benzo[^imidazol-2(3H)-one (intermediate 37) (3.6 g, 72%) as a yellow solid, mp: 249-251C.

Reference： [1]Patent: WO2012/3418,2012,A2 .Location in patent: Page/Page column 71

12
[ 2080-75-3 ]
[ 1354030-43-5 ]

Reference： [1]Patent: WO2012/3418,2012,A2

13
[ 2080-75-3 ]
[ 1354030-44-6 ]

Reference： [1]Patent: WO2012/3418,2012,A2

14
[ 2080-75-3 ]
[ 1354030-53-7 ]

Reference： [1]Patent: WO2012/3418,2012,A2

15
[ 2080-75-3 ]
[ 1354030-54-8 ]

Reference： [1]Patent: WO2012/3418,2012,A2

16
[ 2080-75-3 ]
[ 1354030-70-8 ]

Reference： [1]Patent: WO2012/3418,2012,A2

17
[ 2080-75-3 ]
[ 1354031-65-4 ]

Reference： [1]Patent: WO2012/3418,2012,A2

18
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1]Patent: WO2012/3418,2012,A2
[2]Letters in Organic Chemistry,2011,vol. 8,p. 406 - 411

19
[ 1329028-11-6 ]
[ 2080-75-3 ]

Reference： [1]Letters in Organic Chemistry,2011,vol. 8,p. 406 - 411

20
[ 623-49-4 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1]Letters in Organic Chemistry,2011,vol. 8,p. 406 - 411

21
[ 57-13-6 ]
[ 102-51-2 ]
[ 2080-75-3 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 527 - 529

22
[ 2080-75-3 ]
5-methoxy-6-nitro-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With nitric acid; at 0 - 20℃; for 4h;	5.2 5-Methoxy-6-nitro-1H-benzo[d]imidazol-2(3H)-one (9) A solution of 17.5% fuming nitric acid (12.5 mL, 48.9 mmol) was slowly added to <strong>[2080-75-3]5-methoxy-1H-benzo[d]imidazol-2(3H)-one</strong> (0.25 g, 1.5 mmol) at 0 C, and the reaction was stirred for 1 h at 0 C, and at 20 C for 3 h. The reaction mixture was cooled to 0 C and neutralised with saturated aqueous NaHCO3 solution. The product was extracted with EtOAc (2 * 50 mL), washed with water, dried, and concentrated to give 9 (113 mg, 36%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) delta = 11.21 (br s, 1H), 10.81 (br s, 1H), 7.47 (s, 1H), 6.80 (s, 1H), 3.89 (s, 3H); MS ES+ve m/z 210 (M+H)+, 251 (M+H+MeCN)+.