63655-40-3|2-Amino-1H-benzo[d]imidazole-5-carbonitrile| Ambeed

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Quality Control of [ 63655-40-3 ] Purity: 95% SDS Specification

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Product Details of [ 63655-40-3 ]

CAS No. :	63655-40-3
Formula :	C₈H₆N₄
M.W :	158.16
SMILES Code :	N#CC1=CC=C2NC(N)=NC2=C1
MDL No. :	MFCD01658319
InChI Key :	PNMKRBOIMTZVLQ-UHFFFAOYSA-N
Pubchem ID :	113400

Safety of [ 63655-40-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 63655-40-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	45.21
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.49 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.62
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	1.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.02
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.	0.18
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	1.24
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.09
Solubility	1.29 mg/ml ; 0.00818 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.	-2.37
Solubility	0.671 mg/ml ; 0.00425 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	-2.62
Solubility	0.375 mg/ml ; 0.00237 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	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.	-6.46 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 [ 63655-40-3 ]

* 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.

Downstream synthetic route of [ 63655-40-3 ]

[ 63655-40-3 ] Synthesis Path-Downstream 1~20

Yield	Reaction Conditions	Operation in experiment
87%	In methanol; water; at 50℃; for 1h;	General procedure: O. 5-Bromo-2-aminobenzimidazole (11) 5-Bromo-2-aminobenzimidazole (11) was synthesized according to a modified version of a reported procedure. [31] In brief, 4-bromo-1,2-diaminobenzene (1.0 g, 5.35 mmol, 1.0 eq.) was dissolved in a 1:1 mixture of MeOH (40 mL) and water (40 mL) in a 250 mL round bottom flask. The reaction mixture was treated with CNBr (1.7 g, 16.04 mmol, 3.0 eq.) and heated at 50 C. for 1 h. After cooling to room temperature, the MeOH was removed in vacuo, and the remaining mixture was basified with 1.0 M aq. NaOH (to pH=8.0) and extracted with EtOAc (3*30 mL).

2
[ 506-68-3 ]
[ 17626-40-3 ]
[ 63655-40-3 ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 5226 - 5229.
[2]Heterocycles,2007,vol. 71,p. 647 - 656.

3
[ 107-15-3 ]
[ 63655-40-3 ]
5-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazol-2-ylamine hydrochloride [ No CAS ]

References: [1]Heterocycles,2007,vol. 71,p. 647 - 656.

4
[ 49609-84-9 ]
[ 63655-40-3 ]
2-chloro-N-(5-cyano-1H-benzimidazol-2-yl)-nicotinamide [ No CAS ]

References: [1]Heterocycles,2007,vol. 71,p. 647 - 656.

5
[ 75-31-0 ]
[ 63655-40-3 ]
2-amino-N-isopropyl-1H-benzimidazole-5-carboxamidine hydrochloride [ No CAS ]

References: [1]Heterocycles,2007,vol. 71,p. 647 - 656.

6
[ 506-68-3 ]
[ 17626-40-3 ]
[ 6393-40-4 ]
[ 63655-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	aluminum nickel; In water; ethyl acetate;	D. 2-amino-5-cyanobenzimidazole 3-Nitro-4-aminobenzonitrile (12.5 g.) was hydrogenated at 60 psi with Raney nickel in ethyl acetate at room temperature. The catalyst was filtered and the filtrate was evaporated to dryness in vacuo to provide the crude diamine. The crude 3,4-diaminobenzonitrile (13.3 g.) was stirred in 450 ml. of water. Cyanogen bromide (10.6 g.) was added and the mixture was stirred at room temperature for 3 hours. The reaction mixture rose to 27 C. After reaction, the mixture was filtered to remove some tarry material. The filtrate was basified with sodium carbonate. The basic solution was filtered to remove any dark material, and the filtrate was extracted with ethyl acetate. The ethyl acetate extract was evaporated in vacuo. The residue was crystallized from ethyl acetate-n-hexane to yield 6.4 g. of 2-amino-5-cyanobenzimidazole, m.p. 223-226 C. Analysis C8 H6 N4 MW 158; Calcd: C, 60.75; H, 3.82; Found: C, 60.26; H, 4.04.

References: [1]Patent: US4018790,1977,A .

7
[ 63655-40-3 ]
5-cyano-2-aminobenzimidazole hydrochloride [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 5226 - 5229.

8
[ 41717-28-6 ]
[ 63655-40-3 ]
[ 1422390-95-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In toluene; for 16h;Reflux;	General procedure: To a solution of benzofurane-2-carbonyl chloride 1 in dry toluene, a solution of corresponding anilines and amino-pyridines 2a-j, 2-aminobenzothiazoles 4a, 4c and 5a and 2-aminobenzimidazoles 4b, 4d and 5b in dry toluene was added dropwise, followed by the addition of Et3N. The mixture was refluxed for several hours. After cooling, the resulting products were filtered off and recrystallized from methanol to obtain benzofurane-2-carboxamides 3a, 3b, 3d-j and 6a-f.

References: [1]European Journal of Medicinal Chemistry,2013,vol. 59,p. 111 - 119.

9
2-bromo-1-(2,3-dichlorophenyl)ethanone [ No CAS ]
[ 63655-40-3 ]
[ 1616405-88-9 ]
[ 1616406-32-6 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5702 - 5713.

10
2-bromo-1-(2,3-dichlorophenyl)ethanone [ No CAS ]
[ 63655-40-3 ]
[ 1616406-30-4 ]
[ 1616406-31-5 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5702 - 5713.

11
[ 368869-97-0 ]
[ 63655-40-3 ]
N-(5-cyano-1H-benzo[d]imidazol-2-yl)-2-(2,3-dihydrobenzofuran-5-yl)thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	AL(5-Cyano-lH-benzo[^imidazol-2-yl)-2-(2,3-dihydrobenzofuraii~5-yl)thiazole-4- To a solution of 2-(2,3-dihydro-l-berizofuran-5-yl)-l 3-thiazole-4-carboxylic acid (123 nag, 0.50 mmol) in 2 ml N,N-dimethylformamide, were added 2-amino~lH-benzo[c jimidazole-5- carbonitrile (130 mg, 0.54 mmol), 2-(lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate (HBTU) (188 mg, 0.5 mmol), 4-dimethylaininopyridine (6 mg, 0.05 mmol) and NN-diisopropylethylamine (0.22 ml, 1.24 mmol). The reaction mixture was stirred overnight at room temperature. It was poured into ice water. The foraied precipitate was filtered off and dried. The product was obtained as a light yellow solid (154 mg, 0.40 mmol, 79 % yield). FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-<) delta ppm 3.29 (t, J=8.75 Hz, 2 H), 4.65 (t, J=8.75 Hz, 2 H), 6.91 (d, J=8.34 Hz, 1 H), 7.54 (dd, J=8.25 Hz, j=1.32 Hz, 1 H), 7.67 (d, j=8.28 Hz, 1 H), 7.92 (d, J-1.92 Hz, 1 H), 7.95 (bs, 1 H), 8.13 (bs, 1 H), 8.58 (s, 1 H), 11.84 (bs, 1 H), 12.69 (bs, 1 H). LC/MS [M+H]+: 387.8

References: [1]Patent: WO2014/202638,2014,A1 .Location in patent: Page/Page column 70.

12
[ 4521-61-3 ]
[ 63655-40-3 ]
N-(5-cyanobenzimidazol-2-yl)-3,4,5-trimethoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In toluene; for 24h;Reflux;	General procedure: To a solution of corresponding benzoyl chlorides 2-3 in drytoluene, a solution of <strong>[63655-40-3]2-amino-5(6)-cyanobenzimidazole</strong> 29in dry toluene was added dropwise, followed by the additionof Et3N. The reaction mixture was refluxed for severalhours. After cooling the solution was concentrated and theobtained solid was filtered off and recrystallized fromappropriate solvent.