118469-15-1|5-Fluoro-2-methyl-1H-benzo[d]imidazole| Ambeed

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Quality Control of [ 118469-15-1 ] Purity: 97% SDS Specification

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Product Details of [ 118469-15-1 ]

CAS No. :	118469-15-1
Formula :	C₈H₇FN₂
M.W :	150.15
SMILES Code :	CC1=NC2=C(N1)C=CC(F)=C2
MDL No. :	MFCD00792439
InChI Key :	IWDUKSHNFODGKM-UHFFFAOYSA-N
Pubchem ID :	2775375

Safety of [ 118469-15-1 ]

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

Computational Chemistry of [ 118469-15-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	41.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.39
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	1.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.43
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.	1.75
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	2.9
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.09

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.63
Solubility	0.352 mg/ml ; 0.00234 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.	-2.22
Solubility	0.908 mg/ml ; 0.00605 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	-3.56
Solubility	0.0415 mg/ml ; 0.000277 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.	-5.8 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.	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)	1.71

Application In Synthesis of [ 118469-15-1 ]

* 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 [ 118469-15-1 ]

[ 118469-15-1 ] Synthesis Path-Downstream 1~32

Yield	Reaction Conditions	Operation in experiment
80.4%		B. 2-Methyl-5-fluorobenzimidazole Iron (Fe) (176.75 mmole, 9.87 g) is added to a solution of 4-fluoro-2-nitrophenyl-N-acetamide (35.35 mmole, 7.5 g) in acetic acid (160 ml) and the mixture is refluxed for one hour and is stirred at room temperature over night. The solvent is evaporated. The residue is extracted with ethylacetate and is washed with saturated NaHCO3. The organic layer is washed with water, dried with NaSO4, is filtered and evaporated. Recrystallisation in ethylacetate gives the title compound (80.4%).

2
[ 118469-15-1 ]
[ 1133-49-9 ]
[ 1026534-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; 2,4-dichlorophenoxyacetic acid dimethylamine; mineral oil;	C. 2-Methyl-5-fluoro-1-(3,4,5-trimethoxybenzyl) benzimidazole Sodium hydride (18.31 mmole, 0.44 g, 60% in mineral oil) is added in small amounts under nitrogen to an ice cooled solution of <strong>[118469-15-1]2-methyl-5-fluorobenzimidazole</strong> (16.64 mmole, 2.5 g) in dry DMA (9 ml). The mixture is stirred at the same temperature for 30 minutes. Trimethoxybenzyl chloride (18.31 mmole, 3.97 g) in DMA (4 ml) is added in several portions and the mixture is allowed to stir at room temperature over night. The reaction mixture is poured on to ice, the precipitate is collected and dissolved in dichloromethane. The organic solution is washed several times with water, is dried with Na2SO4, is filtered and is evaporated. (R1=3,4,5-trimethoxybenzyl, R2=CH3, R3=F, n=1, y=0)

References: [1]Patent: US6348032,2002,B1 .

3
[ 367-31-7 ]
[ 2208-07-3 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	In ethanol;	(a) 2-Methyl-5-fluorobenzimidazole Ethyl acetimidate hydrochloride (37.1 g, 0.3 mol) was added to a stirred suspension of 4-fluoro-ortho-phenylenediamine (12.6 g, 0.1 mol) in ethanol (150 ml) at 0 C. The mixture was allowed to warm up to room temperature and stirred overnight. The solvent was removed under reduced pressure and the residue extracted into ethyl acetate (100 ml), washed with water (3*100 ml), dried over anhydrous magnesium sulphate, filtered and evaporated. Crystallisation from ethyl acetate gave 2-methyl-5-fluorobenzimidazole (7.7 g, 51%) as a brown crystalline solid. m.p. 177-178 C. deltaH 7.46 (1H, dd, J 8.8, 4.7 Hz), 7.22 (1H, dd, J 8.9, 2.4 Hz), 6.98 (1H, ddd, J 9.7, 8.9, 2.4 Hz), 2.65 (3H, s).

References: [1]Patent: US5180723,1993,A .

4
[ 367-31-7 ]
[ 123-54-6 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
		Under an N2 atmosphere, 4-fluorobenzene-l,2-diamine (5.0Og, 39.6 mmol) was suspended in EtOH (220 <n="84"/>mL) and 5M HCl (16OmL) was added. The reaction was warmed to 50C and 2,4- pentandione (8.14mL, 7.93mmol) was added and the reaction was heated to reflux for 30 min. Upon cooling to room temperature, the reaction was neutralized with a saturated solution of NaHCO3(aq) and extracted with dichloromethane. The layers were separated and the aqueous layer was washed with additional dichloromethane (2x). The organics were then combined, dried (Na2SO4), filtered and concentrated in vacuo. The resulting solid was triturated with dichloromethane to afford the title compound. 1H NMR (400MHz) (DMSO-d6) delta 7.43-7.19 (bm, 2H); 6.92 (bs, IH); 2.44 (s, 3H).

References: [1]Patent: WO2008/137027,2008,A2 .Location in patent: Page/Page column 81-82.

5
[ 118469-15-1 ]
[ 1080522-29-7 ]
[ 1080522-30-0 ]

Yield	Reaction Conditions	Operation in experiment
		Under an N2 atmosphere, 5-fluoro-2- methyl-lH-benzo[d]imidazole (5.21 g, 34.7mmol) was dissolved in concentrated sulfuric acid (25 mL) and cooled to 0 C. Nitric acid (25 mL) was added and the reaction was stirred at 0 C for 1 h. The reaction was poured over ice and neutralized with IN NaOH. The mixture was extracted with ethyl acetate (3x). The organics were combined, dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with 10% MeOH in dichloromethane to afford l.OOg of 5-fluoro-2-methyl-6-nitro-lH-benzo[d]imidazole after filtration. The filtrate was flash column chromatographed, eluting with 2% to 7% MeOH in dichloromethane, to afford 5-fluoro-2-methyl-4-nitro-lH-benzo[d]imidazole. LC- MS ESI (pos.) m/z: 196.0 (M+H).

References: [1]Patent: WO2008/137027,2008,A2 .Location in patent: Page/Page column 82.

6
[ 57-55-6 ]
[ 367-31-7 ]
[ 118469-15-1 ]
[ 1977-72-6 ]

References: [1]Bulletin of the Chemical Society of Japan,2010,vol. 83,p. 831 - 837.

7
[ 64-17-5 ]
[ 367-31-7 ]
[ 615-15-6 ]
[ 118469-15-1 ]

References: [1]Bulletin of the Chemical Society of Japan,2010,vol. 83,p. 831 - 837.

8
[ 1445-45-0 ]
[ 364-78-3 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With indium; acetic acid; In ethyl acetate; for 4.0h;Reflux; Inert atmosphere;	General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

References: [1]Tetrahedron,2011,vol. 67,p. 8027 - 8033.

9
[ 64-17-5 ]
[ 364-78-3 ]
[ 118469-15-1 ]

References: [1]RSC Advances,2016,vol. 6,p. 72750 - 72755.
[2]Synthetic Communications,2012,vol. 42,p. 1500 - 1508.

10
[ 118469-15-1 ]
[ 73183-34-3 ]
[ 1573171-35-3 ]

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 4287 - 4299.

11
[ 1445-45-0 ]
[ 367-31-7 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 60℃; for 12.0h;	(0618) A mixture of 1,1,1-trimethoxyethane (19.0 g, 159 mmol) and 4-fluorobenzene-1,2-diamine (2.00 g, 15.9 mmol) in MeOH (10 mL) was stirred at 60 C for 12 h. After cooling to ambient temperature, the mixture was concentrated. The residue was purified by flash silica gel chromatography (ISCO; 40 g SepaFlash Silica Flash Column, Eluent of 50100% EA/PE gradient (at) 40 mL/min) to give 5-fluoro-2-methyl-1H-benzo[d]imidazole as a solid.

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 4287 - 4299.
[2]Patent: WO2017/222951,2017,A1 .Location in patent: Page/Page column 84.

12
[ 118469-15-1 ]
[ 98-59-9 ]
5-fluoro-2-methyl-1-tosyl-1H-benzo[d]imidazole [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276.

13
[ 367-31-7 ]
[ 64-19-7 ]
[ 118469-15-1 ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276.

14
[ 141-82-2 ]
[ 367-31-7 ]
[ 118469-15-1 ]

References: [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1337 - 1342.

15
[ 118469-15-1 ]
C₁₁H₁₃NO₄S [ No CAS ]
C₁₉H₂₀FN₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.4%		In a 150 mL round-bottom flask, the benzimidazole compound represented by Formula III (R1 is methyl, R2 is H, R3 is fluorine) (0.306 g, 2.04 mmol) was added, and potassium carbonate was used as the base (0.324 g, 2.35). Acetonitrile was stirred as a solvent at 70C for 30 minutes, cooled to room temperature, compound II (0.400 g, 1.57 mmol) was added, and the temperature was raised to 70C. The reaction was followed by thin layer chromatography to complete the reaction. After concentration, extraction, column chromatography, drying and other post-treatments, compound IV-12 (0.441 g) was obtained with a yield of 69.4%.

References: [1]Patent: CN107721933,2018,A .Location in patent: Paragraph 0084-0086.

16
[ 118469-15-1 ]
[ 105942-09-4 ]
3-fluoro-4-((5-fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 16℃; for 16.0h;	(0621) A mixture of 4-(bromomethyl)-3-fluorobenzonitrile (499 mg, 2.33 mmol) and 5-fluoro-2- methyl-1H-benzo[d]imidazole (350 mg, 2.33 mmol) in DMF (15 mL) was stirred at 16 C for 16 h. The mixture was washed with water (50 mL) and extracted with EtOAc (3 x 30 mL). The collected organic layers were washed with brine (30 mL) and dried over anhydrous Na2SO4. The mixure was filtered and the filtrate was concentrated to get the crude product. The crude product was purified by reverse-phase Prep-HPLC (preparative HPLC on a GILSON 281 instrument fitted with Phenomenex Synergi C18 250x21.2mmx4um using water and acetonitrile as the eluents. Mobile phase A: water, mobile phase B: acetonitrile (containing: 0.1%TFA-ACN). Gradient: 35-65%, 0-10 min; 100% B, 10.5-12.5min; 5% B, 13-15min) to give 3-fluoro-4-((5- fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile as an oil. ESI-MS m/z [M + H]+ : 284.0.

References: [1]Patent: WO2017/222951,2017,A1 .Location in patent: Page/Page column 85.

17
[ 118469-15-1 ]
(Z)-3-fluoro-4-((5-fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-N'-hydroxybenzimidamide [ No CAS ]

References: [1]Patent: WO2017/222951,2017,A1 .

18
[ 118469-15-1 ]
3-(3-fluoro-4-((5-fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole [ No CAS ]

References: [1]Patent: WO2017/222951,2017,A1 .

19
[ 118469-15-1 ]
[ 1080522-40-2 ]
[ 1080522-39-9 ]