50790-93-7|2-Butylimidazole| Ambeed

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Quality Control of [ 50790-93-7 ] Purity: 97% SDS Specification

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Product Details of [ 50790-93-7 ]

CAS No. :	50790-93-7
Formula :	C₇H₁₂N₂
M.W :	124.18
SMILES Code :	CCCCC1=NC=CN1
MDL No. :	MFCD00792664
InChI Key :	SLLDUURXGMDOCY-UHFFFAOYSA-N
Pubchem ID :	11815351

Safety of [ 50790-93-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Computational Chemistry of [ 50790-93-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	5
Fraction Csp3	0.57
Num. rotatable bonds	3
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	37.97
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.	1.47
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	1.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.75
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.	0.67
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	2.29
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.95
Solubility	1.39 mg/ml ; 0.0112 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.	-2.01
Solubility	1.21 mg/ml ; 0.00975 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	-2.79
Solubility	0.2 mg/ml ; 0.00161 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	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.	-5.79 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)	1.69

Application In Synthesis of [ 50790-93-7 ]

* 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 [ 50790-93-7 ]

[ 50790-93-7 ] Synthesis Path-Downstream 1~35

1
[ 107-15-3 ]
[ 109-52-4 ]
[ 50790-93-7 ]

References: [1]Patent: US2847417,1956, .

2
[ 10443-59-1 ]
[ 50790-93-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 6079 - 6082.
[2]Synlett,2004,p. 2803 - 2805.
[3]Canadian Journal of Chemistry,2005,vol. 83,p. 110 - 114.
[4]Tetrahedron Letters,2004,vol. 45,p. 8687 - 8690.
[5]Chemistry of Heterocyclic Compounds,2008,vol. 44,p. 802 - 806.
[6]Synthesis,1980,p. 489 - 490.

3
[ 50790-93-7 ]
[ 83160-36-5 ]
5-(2-Butyl-imidazol-1-ylmethyl)-3,3-diphenyl-dihydro-furan-2-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4415 - 4424.

4
[ 50790-93-7 ]
[ 76513-69-4 ]
[ 134405-73-5 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3858 - 3872.

5
[ 50790-93-7 ]
[ 611-19-8 ]
[ 133485-54-8 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3858 - 3872.

6
[ 50790-93-7 ]
[ 114772-38-2 ]
4'-(2-Butyl-imidazol-1-ylmethyl)-biphenyl-2-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 877 - 885.

7
[ 50790-93-7 ]
[ 114772-40-6 ]
1-<<2'-(tert-butoxycarbonyl)biphenyl-4-yl>methyl>-2-butylimidazole [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1993,vol. 43,p. 828 - 830.
[2]Arzneimittel-Forschung/Drug Research,1993,vol. 43,p. 1157 - 1168.

8
[ 50790-93-7 ]
[ 133051-88-4 ]
2-butyl-1-<<2'-<(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl>imidazole [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1993,vol. 43,p. 1157 - 1168.

9
[ 50790-93-7 ]
[ 100-11-8 ]
2-Butyl-1-(4-nitro-benzyl)-1H-imidazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1312 - 1329.

10
[ 50790-93-7 ]
[ 145575-92-4 ]

References: [1]Heterocycles,1995,vol. 41,p. 161 - 174.
[2]Synthetic Communications,1992,vol. 22,p. 2971 - 2977.

11
[ 50790-93-7 ]
[ 154371-61-6 ]

References: [1]Synthetic Communications,1993,vol. 23,p. 3231 - 3248.

12
[ 542-69-8 ]
[ 23230-39-9 ]
[ 50790-93-7 ]

Yield	Reaction Conditions	Operation in experiment
85%		To a solution of 2b (0.25 g, 2 mmol) in anhydrous THF (10 mL) under Ar atmosphere was added n-BuLi (1.6 M in hexanes, 1.37 mL, 2.20 mmol) dropwise via a syringe at -78 C. After 30 min, DMPU (0.48 mL, 4.0 mmol) was added at -70 C and stirred for additional 30 min before n-BuI (0.27 mL, 2.40 mmol) was added at -78 C. The reaction mixture was allowed to warm to rt over a period of 16 h. Then, aqueous HCl (2 M, 8 mL) was added, the organic solvent was removed and the resulting mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with CH2Cl2 (3 × 15 mL) The organic phase was dried over Na2SO4 and concentrated in vacuo to furnish 5b as a pale yellow oil (0.21 g). Data were consistent with literature. Yield: 85%; Rf 0.54 (CHCl3/MeOH 9:1) tR 5.52 min (5% MeCN ? 100% MeCN in 30 min); ESI-MS (m/z): 125.17 [M + H]; 1H NMR (400 MHz, CDCl3): delta 6.87 (s,2H), 2.68 (t, 2H, J = 7.5 Hz), 1.67 (quint, 2H, J = 7.5 Hz), 1.34 (sext, 2H, J = 7.5 Hz), 0.93 (t, 3H, J = 7.5 Hz); 13C NMR (160 MHz, CDCl3): delta 148.97, 120.84, 30.81, 27.64, 22.20, 12.95.

References: [1]European Journal of Medicinal Chemistry,2013,vol. 62,p. 352 - 370.
[2]Journal of Organic Chemistry,1988,vol. 53,p. 5685 - 5689.

13
(3aα,4α,7α,7aα)-2-butyl-3a,4,7,7a-tetrahydro-4,7-methano-1H-benzimidazole [ No CAS ]
[ 50790-93-7 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 3387 - 3390.

14
[ 542-69-8 ]
[ 61278-81-7 ]
[ 50790-93-7 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4038 - 4040.

15
[ 50790-93-7 ]
[ 50-00-0 ]
[ 68283-19-2 ]
[ 136317-69-6 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 8449 - 8454.

16
[ 50790-93-7 ]
[ 3056-18-6 ]
9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(2-butylimidazol-1-yl)-2-chloropurine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 65℃; for 32h;	Preparation of 6-(2-butylimidazol- 1 -vD-2-chloropurine. A solution of 9-(2,3,5-tri-0-acetyl-beta-D-ribofuranosyi)-2,6-dichloropurine(2.41 g, 5.4 mmol) and <strong>[50790-93-7]2-butylimidazole</strong> (6.68 g, 54 mmol) in CH3CN (60 mL) was stirred at 65 C under N2 for 32 h (reaction complete, TLC). Volatiles were evaporated in vacuo, and the residue was chromatographed (MeOHZCH2Cl2, 1:90) to give crude 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-(2-butylimidazol-l-yl)-2- chloropurine (3.33 g, contaminated with <strong>[50790-93-7]2-butylimidazole</strong>): 1H NMR (500 MHz,CDCl3) delta 8.56 (s, IH), 8.24 (s, IH), 7.10 (s, IH), 6.26 (d, J= 5.8 Hz, IH), 5.83 (t, J = 5.6 Hz, IH), 5.61 (t, J= 5.6 Hz, IH), 4.43-4.51 (m, 3H), 3.31 (t, J= 7.9 Hz, 2H), 2.18 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H), 1.81 (quint, J= 7.7 Hz, 2H), 1.50 (sext, J= 7.7 Hz, 2H), 0.98 (t, J= 7.3 Hz, 3H); HRMS m/z 535.1702 (MH+ [C23H28ClN6O7] = 535.1708).

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4216 - 4221.
[2]Patent: WO2006/138396,2006,A2 .Location in patent: Page/Page column 51.

17
[ 50790-93-7 ]
[ 891497-92-0 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4216 - 4221.

18
[ 50790-93-7 ]
[ 83857-96-9 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 8449 - 8454.
[2]Synthetic Communications,1992,vol. 22,p. 2971 - 2977.

19
[ 50790-93-7 ]
[ 133040-03-6 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 8449 - 8454.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 8449 - 8454.
[3]Synthetic Communications,1993,vol. 23,p. 3231 - 3248.
[4]Synthetic Communications,1993,vol. 23,p. 3231 - 3248.

20
[ 50790-93-7 ]
[ 133040-02-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 8449 - 8454.

21
[ 50790-93-7 ]
[ 159708-89-1 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 8449 - 8454.

22
[ 50790-93-7 ]
[ 68282-49-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 8449 - 8454.
[2]European Journal of Medicinal Chemistry,2016,vol. 108,p. 605 - 615.

23
[ 50790-93-7 ]
[ 133040-01-4 ]