870837-70-0|4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde| Ambeed

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Quality Control of [ 870837-70-0 ] Purity: 97% SDS Specification

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Product Details of [ 870837-70-0 ]

CAS No. :	870837-70-0
Formula :	C₁₁H₁₀N₂O₂
M.W :	202.21
SMILES Code :	O=CC1=CC=C(N2C=CN=C2)C(OC)=C1
MDL No. :	MFCD13180653
InChI Key :	BFARODQVUOAKSJ-UHFFFAOYSA-N
Pubchem ID :	73014044

Safety of [ 870837-70-0 ]

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

Computational Chemistry of [ 870837-70-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	11
Fraction Csp3	0.09
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	55.44
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	44.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.77
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	1.11
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.69
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.	0.38
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	1.64
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.32

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.14
Solubility	1.47 mg/ml ; 0.00728 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.	-1.63
Solubility	4.74 mg/ml ; 0.0235 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	-3.01
Solubility	0.198 mg/ml ; 0.000979 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.	-6.75 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	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)	1.65

Application In Synthesis of [ 870837-70-0 ]

* 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 [ 870837-70-0 ]

[ 870837-70-0 ] Synthesis Path-Downstream 1~21

1
[ 870837-70-0 ]
[ 870837-69-7 ]
[ 870837-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; In chloroform; for 1.5h;Heating / reflux;	To a chloroform (3 mL) solution of the <strong>[870837-70-0]4-(1H-imidazol-1-yl)-3-methoxybenzaldehyde</strong> (50 mg) obtained in Example 111, N-chlorosuccinimide (35 mg) was added, and the reaction solution was heated to reflux for 1.5 hours. The reaction mixture was allowed to be cooled and then purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate system), and 4-(2-chloro-1H-imidazol-1-yl)-3-methoxybenzaldehyde (13 mg) and 4-(5-chloro-1H-imidazol-1-yl)-3-methoxybenzaldehyde (14 mg) were obtained. The physical properties of 4-(2-chloro-1H-imidazol-1-yl)-3-methoxybenzaldehyde are as follows. 1H-NMR (CDCl3) delta (ppm): 3.92 (s, 3H), 7.04 (d, J=1.4 Hz, 1H), 7.10 (d, J=1.4 Hz, 1H), 7.48 (d, J=8 Hz, 1H), 7.57-7.59 (m, 2H), 10.6 (s, 1H). The physical properties of 4-(5-chloro-1H-imidazol-1-yl)-3-methoxybenzaldehyde are as follows. 1H-NMR (CDCl3) delta (ppm): 3.92 (s, 3H), 7.10 (s, 1H), 7.47 (d, J=8 Hz, 1H), 7.58-7.60 (m, 3H), 10.6 (s, 1H)

References: [1]Patent: US2006/4013,2006,A1 .Location in patent: Page/Page column 59-60.

2
[ 870837-70-0 ]
[ 105-56-6 ]
C₁₆H₁₅N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In ethanol; for 3.5h;Heating / reflux;	Cyano ethyl acetate (76.0 muL) and piperidine were added one by one to an ethanol solution (5.0 mL) of 4-(1H-imidazol-1-yl-3-methoxybenzaldehyde (144 mg) obtained in Example 111 (35.0 muL). The reaction solution was refluxed for 3.5 hours, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the crude ester product

References: [1]Patent: US2006/4013,2006,A1 .Location in patent: Page/Page column 72.

3
[ 288-32-4 ]
[ 870837-18-6 ]
[ 870837-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃;	Potassium carbonate (6.70 g) and imidazole (2.60 g) were added to a DMF (30 mL) solution of 4-fluoro-3-methoxybenzaldehyde (5.00 g) one by one, and the reaction solution was agitated at 130 C. overnight. After confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and 4.76 g of crude aldehyde compounds was obtained by condensing under reduced pressure. The physical properties of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 10.01 (s, 1H), 7.92 (s, 1H), 7.57-7.60 (m, 2H), 7.49 (d, J=7.6 Hz, 1H), 7.29 (s, 1H), 7.21 (s, 1H), 3.98 (s, 3H).

References: [1]Patent: US2006/4013,2006,A1 .Location in patent: Page/Page column 77.

4
[ 870837-70-0 ]
[ 5927-18-4 ]
(E)-3-[4-(1H-imidazol-1-yl)-3-methoxyphenyl)acrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Dimethylphosphonoacetic acid methyl ester (3.80 mL) and lithium hydroxide monohydrate (1.20 g) were added one by one to a THF (20 mL) solution of the crude aldehyde compound (4.76 g) obtained above, and the reaction solution was agitated overnight at the room temperature. 2N sodium hydroxide solution was added to the reaction solution after confirming disappearance of the starting materials (20 mL), and the reaction solution was agitated at 50 C. for 2 hours. The reaction solution was cooled to 0 C., 2N hydrochloric acid was added to the reaction solution (20 mL), and deposited precipitation was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 4.2 g of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 7.96 (s, 1H), 7.63 (d, J=16 Hz, 1H), 7.60 (d, J=1.6 Hz, 1H), 7.48 (s, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.39 (dd, J=1.6, 8.0 Hz, 1H), 7.06 (s, 1H), 6.68 (d, J=16 Hz, 1H), 3.90 (s, 3H).

References: [1]Patent: US2006/4013,2006,A1 .Location in patent: Page/Page column 77.

5
[ 288-32-4 ]
[ 128495-46-5 ]
[ 870837-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	1H-imidazole (42.0 mg) and potassium carbonate (180 mg) were added to a solution of 4-fluoro-3-methoxybenzaldehyde (100 mg) in DMF (2.0 mL), and the reaction solution was stirred at 80C overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system -> ethyl acetate-methanol system) to obtain 36.2 mg of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 3.98 (s, 3H), 7.21 (s, 1H), 7.30 (s, 1H), 7.48 (d, J = 7.6 Hz, 1H), 7.56-7.60 (m, 2H), 7.92 (s, 1H), 10.0 (s, 1H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃;	l-(4-Ethynyl-2-methoxyphenyl)-l//-imidazole.A mixture of 4-fiuoro-3-methoxybenzaldehyde (1.0 g, 6.5 mmol) in 20 mL of DMF was treated with 4-methylimidazole (1.0 g, 15 mmol) and warmed to 130 C. Stirred overnight. Diluted with EtOAc, washed with sat'd NaHCO3, dried (Na2SO4), concentrated. Dissolved in 20 mL of MeOH, treated with K2CO3 (2.0 g, 14 mmol) and dimethyl (l-diazo-2-oxopropyl)phosphonate (1.5 g, 7.8 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), cone. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne:1H NMR (600 MHz, CDCl3) delta7.79 (s, 1 H), 7.18 (t, J= 1.2 Hz, 1 H), 7.16 (d, J= 1.8 Hz, 1 H), 7.15 (m, 2 H), 7.13 (d, J= 1.5 Hz, 1 H).

References: [1]Patent: EP2019093,2009,A1 .Location in patent: Page/Page column 45.
[2]Patent: WO2008/156580,2008,A1 .Location in patent: Page/Page column 32.

6
[ 870837-70-0 ]
[ 958245-14-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 2.0h;	2-Methyl-2-butene (5.0 mL), sodium dihydrogenphosphate dihydrate (1.55 g) and sodium chlorite (3.14 g) were added to a solution containing <strong>[870837-70-0]4-(1H-imidazol-1-yl)-3-methoxybenzaldehyde</strong> (2 g) in water (10 mL) and tert-butanol (30 mL), and the reaction solution was stirred for two hours. The generated solid was collected by filtration to obtain the title compound (745 mg). The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 3.89 (s, 3H), 7.09 (s, 1H), 7.54 (m, 2H), 7.63 (dd, J = 8.0, 1.6 Hz, 1H), 7.69 (d, J = 1.6 Hz, 1H), 8.05 (s, 1H).

References: [1]Patent: EP2019093,2009,A1 .Location in patent: Page/Page column 45-46.

7
[ 1269834-33-4 ]
[ 870837-70-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014.

8
[ 870837-70-0 ]
[ 123-54-6 ]
C₂₇H₂₄N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%		General synthesis of curcumin analogues 25-34 from corresponding benzaldehyde precursors was carried out by modified literature methods (Scheme 5). The appropriate vanillin derivative (1 equiv) and boric anhydride (0.6 equiv), dissolved in anhydrous DMF in a flask which was thoroughly flushed with nitrogen before use, were stirred at room temperature. Under nitrogen, 2,4-pentanedione (0.6 equiv) and 2,2-dimethoxypropane (1 equiv) or tributyl borate (2 equiv) were added dropwise. The mixture was stirred and heated to a temperature of 70 C under nitrogen. About 30 min later, n-butylamine (0.2 equiv) was added dropwise slowly under nitrogen, and the mixture was allowed to stir at 70 C for 2-4 h. At the end of the reaction, the mixture was hydrolyzed by adding hot (70 C) aqueous 5% acetic acid and stirred until it cooled down. The mother liquor was extracted three times with EtOAc, and the combined organic layers were washed three times, dried over anhydrous Na2SO4, and filtered. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography.

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014.

9
[ 1269834-29-8 ]
[ 870837-70-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014.

10
[ 35387-92-9 ]
[ 870837-70-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014.

11
[ 41608-64-4 ]
[ 870837-70-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014.
[2]Patent: US2006/4013,2006,A1 .

12
[ 870837-70-0 ]
[ 90965-06-3 ]
[ 1093980-61-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol;	l-(4-Ethynyl-2-methoxyphenyl)-l//-imidazole.A mixture of 4-fiuoro-3-methoxybenzaldehyde (1.0 g, 6.5 mmol) in 20 mL of DMF was treated with 4-methylimidazole (1.0 g, 15 mmol) and warmed to 130 C. Stirred overnight. Diluted with EtOAc, washed with sat'd NaHCO3, dried (Na2SO4), concentrated. Dissolved in 20 mL of MeOH, treated with K2CO3 (2.0 g, 14 mmol) and dimethyl (l-diazo-2-oxopropyl)phosphonate (1.5 g, 7.8 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), cone. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne:1H NMR (600 MHz, CDCl3) delta7.79 (s, 1 H), 7.18 (t, J= 1.2 Hz, 1 H), 7.16 (d, J= 1.8 Hz, 1 H), 7.15 (m, 2 H), 7.13 (d, J= 1.5 Hz, 1 H).

References: [1]Patent: WO2008/156580,2008,A1 .Location in patent: Page/Page column 32.

13
[ 288-32-4 ]
[ 120-14-9 ]
[ 870837-62-0 ]
[ 870837-70-0 ]