108511-97-3|Isoxazol-4-amine| Ambeed

Structure of 1,2-oxazol-4-amine
CAS No.: 108511-97-3

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Quality Control of [ 108511-97-3 ] Purity: 97% SDS Specification

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Product Details of [ 108511-97-3 ]

CAS No. :	108511-97-3
Formula :	C₃H₄N₂O
M.W :	84.08
SMILES Code :	NC1=CON=C1
MDL No. :	MFCD08234629
InChI Key :	CVCYZCBJCQXUCN-UHFFFAOYSA-N
Pubchem ID :	13804278

Safety of [ 108511-97-3 ]

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

Computational Chemistry of [ 108511-97-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	6
Num. arom. heavy atoms	5
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	20.91
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.	0.84
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	-0.31
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.26
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.	-1.13
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	0.42
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.78
Solubility	13.9 mg/ml ; 0.165 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.	-0.32
Solubility	40.0 mg/ml ; 0.476 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.77
Solubility	14.3 mg/ml ; 0.17 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	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.	-7.03 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	2.0
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)	2.34

Application In Synthesis of [ 108511-97-3 ]

* 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 [ 108511-97-3 ]

[ 108511-97-3 ] Synthesis Path-Downstream 1~31

1
[ 1121-13-7 ]
[ 108511-97-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; zinc; In water; at 0 - 5℃; for 2h;	4- Nitroisoxazole (may be prepared as described in Description 94; 850 mg, 7.45 mmol) was added to a solution of ammonium chloride (9169 mg, 171 mmol) in water (60 ml). The resultant suspension was cooled to 0°C, and zinc (4142 mg, 63.3 mmol) was added in portions whilst keeping the temperature below 5°C. After the addition, the mixture was stirred at 0-5°C for 2 hours. The reaction mixture was then filtered, and the filtrate was extracted with ethyl acetate (100 ml x 4). The organic phase was washed by water (100 ml x 2), dried over anhydrous MgS04, and concentrated to yield the title compound as a brown oil, 535 mg.

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 2714 - 2726.
[2]Patent: WO2011/38572,2011,A1 .Location in patent: Page/Page column 76.

2
[ 463-71-8 ]
[ 108511-97-3 ]
[ 122686-01-5 ]

References: [1]Helvetica Chimica Acta,1989,vol. 72,p. 556 - 569.

3
[ 122686-14-0 ]
[ 108511-97-3 ]

References: [1]Helvetica Chimica Acta,1989,vol. 72,p. 556 - 569.

4
[ 98818-51-0 ]
[ 108511-97-3 ]
[ 149976-34-1 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3100 - 3107.

5
[ 1885-14-9 ]
[ 108511-97-3 ]
[ 1190843-61-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With pyridine; In tetrahydrofuran; at 0 - 20℃;	To a solution of <strong>[108511-97-3]4-aminoisoxazole</strong> (2.00 g, 23.79 mmol; CASNo. 108511-97-3) in THF (50 mL) at 0 0C was added pyridine (1.92 mL, 23.79 mmol,) followed by phenyl chloroformate (3.28 mL, 26.17 mmol,). After stirring at 0 0C for 2.5 h, the reaction was warmed to room temp overnight. The reaction was diluted with ethyl acetate and washed with 2M HCI, water, saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography (dichloromethane/hexane) to give the title compound as a white solid (2.07 g, 10.15 mmol, 50percent).
50%	With pyridine; In tetrahydrofuran; at 0 - 20℃;	To a solution of <strong>[108511-97-3]4-aminoisoxazole</strong> (2.00 g, 23.79 mmol; CASNo. 108511-97-3) in THF (50 mL) at 0 0C was added pyridine (1.92 mL, 23.79 mmol,) followed by phenyl chloroformate (3.28 mL, 26.17 mmol,). After stirring at 0 0C for 2.5 h, the reaction was warmed to room temp overnight. The reaction was diluted with ethyl acetate and washed with 2M HCI1 water, saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography40 (dichloromethane/hexane) to give the title compound as a white solid (2.07 g, 10.15 mmol, 50percent).
50%	With pyridine; In tetrahydrofuran; at 0 - 20℃;	To a solution of <strong>[108511-97-3]4-aminoisoxazole</strong> (2.00 g, 23.79 mmol; CASNo. 108511-97-3) in THF (50 mL) at 0 0C was added pyridine (1.92 mL, 23.79 mmol,) followed by phenyl chloroformate (3.28 mL, 26.17 mmol,). After stirring at 0 0C for 2.5 h, the reaction was warmed to room temp overnight. The reaction was diluted with ethyl acetate and washed with 2M HCI, water, saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography (dichloromethane/hexane) to give the title compound as a white solid (2.07 g, 10.15 mmol, 50percent).

References: [1]Patent: WO2009/127943,2009,A1 .Location in patent: Page/Page column 29.
[2]Patent: WO2009/127944,2009,A1 .Location in patent: Page/Page column 30.
[3]Patent: WO2009/127948,2009,A1 .Location in patent: Page/Page column 30.

6
[ 1167626-08-5 ]
[ 108511-97-3 ]
[ 1168156-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 50℃; for 16h;Inert atmosphere;	To a suspension of 65 mg of 6-(pyridin-2-yl)imidazo[1,2-a]pyridine-2-carboxylic acid (intermediate 2) and 104 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 2 mL of anhydrous pyridine, placed under argon, are added 68 mg of <strong>[108511-97-3]isoxazol-4-ylamine</strong>. The reaction mixture is stirred for 16 hours at 50° C. and then concentrated under reduced pressure. The residue is taken up in dichloromethane and washed with water. The organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure to give 49 mg of N-(isoxazol-4-yl)-6-(pyridin-2-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid.

References: [1]Patent: US2010/317686,2010,A1 .Location in patent: Page/Page column 8; 9.

7
[ 478040-59-4 ]
[ 108511-97-3 ]
[ 1168157-29-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 50℃; for 16h;	To a suspension of 200 mg of 6-iodoimidazo[1,2-a]pyridine-2-carboxylic acid and 266 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 1 mL of anhydrous pyridine are added 175 mg of <strong>[108511-97-3]isoxazol-4-ylamine</strong>. The reaction mixture is stirred for 16 hours at 50° C. and then concentrated under reduced pressure. The residue is taken up in 10 mL of a mixture of chloroform and water (1/1). The solid is triturated with 3 mL of water, filtered off by suction and washed with 3 mL of water and then with 3 mL of ethyl ether, and dried to give 280 mg of 6-iodo-N-(isoxazol-4-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid. 1H NMR spectrum (DMSO-d6, delta in ppm): 10.93 (broad s, 1H), 9.24 (broad s, 1H), 9.02 (broad s, 1H), 8.81 (broad s, 1H), 8.43 (broad s, 1H), 7.60-7.48 (m, 2H). Mass spectrum (APCI): m/z=258 [M+H]+.

References: [1]Patent: US2010/317686,2010,A1 .Location in patent: Page/Page column 14.

8
[ 1237517-77-9 ]
[ 108511-97-3 ]
[ 1285514-44-4 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 100 mg, 0.30 mmol), EDC (172 mg, 0.90 mmol) and HOBT (137 mg, 0.90 mmol) in dimethylformamide (3 ml) was stirred in air at room temperature for 1 h, then <strong>[108511-97-3]4-isoxazolamine</strong> (may be prepared as described in Description 95; 100 mg, 1.189 mmol) was added in one charge. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (30 mi). The solid was filtered and dried in vacuo to obtain crude product, which was purified with Prep- HPLC (Waters, X-Bridge, 5Mm;30x100mm; A=0.05percentNH3.H2O/water, B:MeCN;v=30ml/min;0-7min, 42percent-54percent; 7-12min, 95percent; t=8.0min.) to yield the title compound as a white solid. 34 mg.'HNMR (400 MHz, DMSO-d6): 10.60 (s, 1 H), 9.27 (s, 1 H), 8.65 (s, 1 H), 8.62 (d, 2H, J=5.6), 8.08 {d, 1 H, J=2.0), 7.98 (dd, 1 H, J=2.0, 8.4), 7.74 (d, 2H, J=5.6), 7.52 (d, 2H, J=7.6), 7.42-7.33 (m, 4H), 5.36 (s, 2H).MS (electrospray); m/z [M+H]+ = 372.1

References: [1]Patent: WO2011/38572,2011,A1 .Location in patent: Page/Page column 128; 129.

9
[ 1285517-57-8 ]
[ 108511-97-3 ]
[ 1285515-76-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	A mixture of 2-[(4-fluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)benzoic acid (may be prepared as described in Description 121 ; 100 mg, 0.31 mmol), isoxazol-4- amine (38.6 mg, 0.46 mmol), HOBT (70.4 mg, 0.46 mmol) and EDC (88 mg, 0.46 mmol) in N,N-dimethyIformamide (5 ml) was stirred at room temperature for 16 hours. Water (50 ml) was added. The mixture was extracted with ethyl acetate (50 ml x 3). The combined organic layers were washed with brine (50 ml), dried over Na2S04, and concentrated to give the crude product. The crude product was purified by a prep-HPLC (Instrument : Gilson GX-281 ; Column: Shimadzu PRC-ODS, 15.0 um, 19 mm * 250 mm; Mobile Phase: A:0.05percent NH3H20/H2O;B:CH3CN; Gradient 0-8min 42-54percentB;8-12min 95percent; Flow ate(ml/min) 30.00; Detective Wavelength (nm) 214; Retention Time(min) 7.5) to yield the title compound as a white solid. 17 mg.1HNMR (400 MHz, DMSO-cf6): 3.85 (3H, s), 5.25 (2H, s), 7.20-7.26 (3H, m), 7.53-7.55 (2H, q), 7.67-7.70 ( H, dd, J - 2.4 Hz, J = 8.8 Hz), 7.79 (1 H, d, J = 2.4 Hz), 7.85 (1 H, s), 8.13 (1 H, s), 8.63 (1H, s), 9.24 (1 H, s), 10.49 (1H, s)MS (electrospray): m/z [M+H]+ =393.1

References: [1]Patent: WO2011/38572,2011,A1 .Location in patent: Page/Page column 187.

10
[ 598-21-0 ]
[ 108511-97-3 ]
2-bromo-N-(isoxazol-4-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydrogencarbonate; sodium carbonate; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere;	To a stirred solution of <strong>[108511-97-3]<strong>[108511-97-3]isoxazol-4-amin</strong>e</strong> (200 mg, 1.66 mmol) in CH2C12 (5 mL) under inert atmosphere were added 2 N Na2CO3 solution (2.6 mL), saturated NaHCO3 solution (5.6 mL), and bromo acetyl bromide (669 mg, 3.33 mmol) at 0 °C. The reaction mixture was warmed to RT and stirred for 1 h. The reaction progress was monitored by TLC; after reaction completion, the reaction mixture was diluted with water (15 mL) and extracted with CH2C12 (2 x 25 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude material. The crude material was purified through silica gel flash column chromatography using 25percent EtOAc/ hexanes to afford compound 1 (300 mg, 88percent) as an off-white solid. 1HNMR (400 MHz, CDC13): oe 8.99 (s, 1H), 8.43 (s, 1H), 8.10 (br s, 1H), 4.04 (s, 2H). LC-MS:98.0percent; (M+2) Found=203.5; (column: X Select C-18, 50 x 3.0 mm, 3.5 jim); RT 1.80 mm. 5 mM NH4OAc: ACN; 0.8 mL/min).

References: [1]Patent: WO2015/48301,2015,A1 .Location in patent: Paragraph 00417.

11
[ 847490-69-1 ]
[ 108511-97-3 ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 13580 - 13584.
Angew. Chem.,2016,vol. 128,p. 13778 - 13782,5.

12
[ 1161-13-3 ]
[ 108511-97-3 ]
benzyl (S)-(1-(isoxazol-4-ylamino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]