81803-60-3|Ethyl imidazo[1,5-a]pyridine-3-carboxylate| Ambeed

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Quality Control of [ 81803-60-3 ] Purity: 97% SDS Specification

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Product Details of [ 81803-60-3 ]

CAS No. :	81803-60-3
Formula :	C₁₀H₁₀N₂O₂
M.W :	190.20
SMILES Code :	O=C(C1=NC=C2C=CC=CN21)OCC
MDL No. :	MFCD10697855
InChI Key :	YDWAMSXHNSBIGG-UHFFFAOYSA-N
Pubchem ID :	13639217

Safety of [ 81803-60-3 ]

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

Computational Chemistry of [ 81803-60-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	9
Fraction Csp3	0.2
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	51.28
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.41
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	2.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.51
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.	0.94
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	1.09
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.81
Solubility	0.295 mg/ml ; 0.00155 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.	-2.96
Solubility	0.21 mg/ml ; 0.0011 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	-2.57
Solubility	0.513 mg/ml ; 0.0027 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.	-5.76 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)	1.94

Application In Synthesis of [ 81803-60-3 ]

* 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 [ 81803-60-3 ]

[ 81803-60-3 ] Synthesis Path-Downstream 1~28

1
[ 81803-59-0 ]
[ 80537-14-0 ]
[ 81803-60-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 1119 - 1122.

2
ethyl 2-azido-3-(2-pyridyl)propenoate [ No CAS ]
[ 80537-14-0 ]
[ 81803-60-3 ]

References: [1]Journal of the Chemical Society. Chemical communications,1982,p. 4 - 6.

3
[ 46460-25-7 ]
[ 81803-60-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With phosphorus pentoxide; trichlorophosphate; at 110℃; for 5.0h;	A solution of ethyl [(pyridin-2-ylmethyl)carbamoyl]fonTlate (1.00 g, 4.80 mmol, 1.00 equiv) and phosphorus pentoxide (3.41 g, 24.02 mmol, 5.00 equiv) in phosphorus oxychloride (30 mL) was stirred for 5 h at 110 C. The resulting mixture was concentrated under vacuum. The residue waspurified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:1). This resulted in 635 mg (70%) of the title compound as a yellow solid. LC-MS (ES, m/z): 191 [M+H] .
44%		A solution of ethyl oxo[(pyridin-2-ylmethyl)amino]acetate (40 g, 192 mmol) in POCl3 (300 mL) was heated to reflux for 18 h. The mixture was concentrated and saturated aqueous NaHCO3 was added. The mixture was extracted with EtOAc (3 x, 500 mL) and the combined organic extracts were washed with saturated brine, dried over Na2SO4, filtered, and concentrated to give a black oily solid. The residue was purified by silica gel chromatography (12%-70% EtOAc/Hexanes) to give the title compound (16 g, 44%). MS 191.1 (M + 1).
2.4 g	With pyridine; trifluoroacetic anhydride; In dichloromethane; at -15 - -10℃; for 12.0h;	2-(Aminomethyl)pyridine (1.5 g, 13.9 mmol) and pyridine (3.62 g, 45.8 mmol) were dissolved in CH2Cl2 (20 mL), and the solution was cooled by using an ice bath. A solution of ethyl oxalyl chloride (1.89 g, 13.9 mmol) in CH2Cl2 (10 mL) was added dropwise at 0 to -5 C. After addition, the mixture was stirred for 2 h and a solution of TFAA (3.06 g, 14.6 mmol) in CH2Cl2 (10 mL) was added dropwise at -15 to -10 C (ice-salt bath). The reaction mixture was allowed to stand overnight in the bath, then washed with sat. aq NaHCO3, and the CH2Cl2 layer was dried over Na2SO4 and concentrated. Yield: 2.4 g (91%); white solid; mp 80 C (Lit. [13] 80 C). The 1H and 13C NMR spectroscopic data were identical to those reported previously. [4,14,18]

References: [1]Patent: WO2015/25025,2015,A1 .Location in patent: Page/Page column 411; 412.
[2]Patent: WO2008/85302,2008,A1 .Location in patent: Page/Page column 96.
[3]Organic Letters,2013,vol. 15,p. 2290 - 2293.
[4]Synthesis,2016,vol. 48,p. 4269 - 4277.

4
[ 81803-60-3 ]
[ 885276-59-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; triethylamine; In acetonitrile; at 0℃; for 1.0h;Cooling with ice;	To an ice cold solution of ethyl imidazo[l,5-alpha]pyridine-3-carboxylate (10 g, 52.6 mmol) in acetonitrile (500 mL) was added N-bromo succinimide (9.36 g, 52.6 mmol). The mixture was allowed to stir for 1 h at which time triethylamine (10 mL) was added to the deep red- violet solution. The color dissipated and the solution was concentrated. Purification of the crude solid by silica gel chromatography (0-20% EtOAc/Hexanes) provided a white crystalline solid (13.5 g 95%). MS 268.9 (M + 1)
	With bromine; acetic acid; at 20℃; for 0.08333330000000001h;	To a solution of <strong>[81803-60-3]ethyl imidazo[1,5-a]pyridine-3-carboxylate</strong> (152 mg) in Acetic Acid (0.25M) was added Bromine (leq). The reaction was stirred at room temperature for 5 minutes thenconcentrated to dryness to give 205 of the title compound. This intermediate was taken onto the next step without purification.

References: [1]Patent: WO2008/85302,2008,A1 .Location in patent: Page/Page column 96.
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1086 - 1089.
[3]Patent: WO2015/25025,2015,A1 .Location in patent: Page/Page column 258.

5
[ 39484-31-6 ]
[ 81803-60-3 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 284 - 286.

6
[ 3731-51-9 ]
[ 4755-77-5 ]
[ 81803-60-3 ]