4-(1,3-Oxazol-5-yl)aniline

Cat.NO.:A132786 Purity:97%

Product Details of [ 1008-95-3 ]

CAS No. :	1008-95-3
Formula :	C₉H₈N₂O
M.W :	160.17
SMILES Code :	NC1=CC=C(C=C1)C1=CN=CO1
MDL No. :	MFCD00052192
Boiling Point :	No data available
InChI Key :	SLJBMRSOKUTXDF-UHFFFAOYSA-N
Pubchem ID :	517747

Safety of [ 1008-95-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 1008-95-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	46.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.54
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	1.32
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.93
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.	0.44
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	1.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.28
Solubility	0.846 mg/ml ; 0.00528 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.	-2.01
Solubility	1.55 mg/ml ; 0.00968 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	-3.38
Solubility	0.066 mg/ml ; 0.000412 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.	-6.34 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	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)	2.05

Application In Synthesis of [ 1008-95-3 ]

* 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.

Upstream synthesis route of [ 1008-95-3 ]

[ 1008-95-3 ] Synthesis Path-Upstream 1~8

1
[ 1014-23-9 ]
[ 1008-95-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride; tin In ethanol; water at 20℃; for 2 h;	To a solution of 5-(4-nitro-phenyl)-oxazole (500mg, 2.6mmol) in ethanol (10ml) was added tin (620mg, 5.2mmol), followed by dropwise addition of concentrated hydrochloric acid (ImI) and then the reaction was stirred at room temperature for 2hr. The reaction mixture was filtered and the filtrate evaporated to dryness. The resultant residue was diluted with water (10ml), basified with saturated bicarbonate solution, then extracted with ethyl acetate. The organic layer was separated, washed with water, dried and concentrated to dryness to yield 4-oxazol-5-yl-phenylamine (380mg, 90percent) as solid.
89%	With hydrogenchloride; iron In ethanol at 0 – 25℃; for 17 h;	[00516] To a solution of 5-(4-nitrophenyl)oxazole (400 mg, 2.10 mmol) in EtOH (5 mL) was added Fe (62 mg, l lmmol) and HCl (2ml,6N) at 0 °C. The reaction was stirred at 0 °C for 1 h and then at 25 °C for 16 h. The solution was diluted with DCM (20 mL) and neutralized with NaHC03 to pH 7 (10 mL x 2), dried (Na2S04), filtered and concentrated in vacuo, the crude product was purified by chromatography (silica, ethyl acetate/petroleum ether =1/1) to afford 4-(oxazol-5-yl)benzenamine (300 mg, 1.87 mmol, 89percent) as a yellow solid. ESI-MS (EI+, m/z): 161.2 [M+H]+.

References:

[1] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 66-67.

[2] Patent: WO2018/191146, 2018, A1, . Location in patent: Paragraph 00516.

[3] Patent: EP1612204, 2006, A1, . Location in patent: Page/Page column 20.

2
[ 1014-23-9 ]
[ 7439-89-6 ]
[ 1008-95-3 ]

References:

[1] Patent: US2004/204386, 2004, A1, .

3
[ 267648-15-7 ]
[ 1008-95-3 ]

References:

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 12, p. 2059 – 2063.

4
[ 5274-71-5 ]
[ 1008-95-3 ]

References:

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 12, p. 2059 – 2063.

5
[ 7745-93-9 ]
[ 1008-95-3 ]

References:

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 12, p. 2059 – 2063.

6
[ 470715-98-1 ]
[ 1008-95-3 ]

References:

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 12, p. 2059 – 2063.

7
[ 38622-91-2 ]
[ 555-16-8 ]
[ 1008-95-3 ]

References:

[1] Patent: US6344465, 2002, B1, . Location in patent: Page column 17-18.

8
[ 555-16-8 ]
[ 1008-95-3 ]

References:

[1] Patent: WO2006/123145, 2006, A1, .

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