[ CAS No. 68302-57-8 ] {[proInfo.proName]}

Name: 68302-57-8|2-Amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid|98%
Brand: Ambeed
SKU: A228799
Price: 5.0 USD
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Quality Control of [ 68302-57-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 68302-57-8 ]

SDS Specification

Alternatived Products of [ 68302-57-8 ]

Product Details of [ 68302-57-8 ]

CAS No. :	68302-57-8	MDL No. :	MFCD00864790
Formula :	C₁₆H₁₄N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SGRYPYWGNKJSDL-UHFFFAOYSA-N
M.W :	298.29	Pubchem ID :	2161
Synonyms :	AA673;Amoxanox;Amoxanox, Brand name: Aphthasol.;Elics;CHX3673

Calculated chemistry of [ 68302-57-8 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.19
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	83.73
TPSA :	106.42 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	3.08
Log Po/w (WLOGP) :	2.75
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	2.64
Consensus Log Po/w :	2.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.97
Solubility :	0.0321 mg/ml ; 0.000107 mol/l
Class :	Soluble
Log S (Ali) :	-4.98
Solubility :	0.00311 mg/ml ; 0.0000104 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.74
Solubility :	0.0054 mg/ml ; 0.0000181 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.91

Safety of [ 68302-57-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 68302-57-8 ]

* 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 [ 68302-57-8 ]
Downstream synthetic route of [ 68302-57-8 ]

[ 68302-57-8 ] Synthesis Path-Upstream 1~3

1
[ 68301-99-5 ]
[ 68302-57-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1985, vol. 28, # 5, p. 559 - 586

2
[ 50743-32-3 ]
[ 68302-57-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1985, vol. 28, # 5, p. 559 - 586

3
[ 68302-57-8 ]
[ 68301-99-5 ]

Reference： [1] Molecular Pharmacology, 2018, vol. 94, # 4, p. 1210 - 1219

[ 68302-57-8 ] Synthesis Path-Downstream 1~21

1
[ 68302-57-8 ]
[ 104636-45-5 ]
[ 100157-23-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4432 - 4437

2
[ 68302-57-8 ]
[ 104636-46-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4432 - 4437

3
[ 68301-99-5 ]
[ 68302-57-8 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 559 - 586

5
[ 50743-32-3 ]
[ 68302-57-8 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 559 - 586

Yield	Reaction Conditions	Operation in experiment
		[spraying powder] amlexanox: 25 g hydroxypropylmethylcellulose: 20 g corn starch: 25 g L-HPC: 30 g

7
[ 6284-40-8 ]
[ 68302-57-8 ]
amlexanox meglumine salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; for 0.0333333h;	The compositions of instantly soluble <strong>[68302-57-8]amlexanox</strong> formulations with meglumine are listed in the Table below. The compositions were prepared by mixing of weighted amounts of dry powders for 90 minutes in a planetary mixer. Dissolution of the formulation was tested by placing the 85 mg of powder formulation in 5 mL water. The solution becomes clear in less than 2 minutes.

Reference： [1]Patent: US2007/135473,2007,A1 .Location in patent: Page/Page column 9

8
[ 68302-57-8 ]
2-amino-7-isopropyl-1-azaxanthone-3-carboxylic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water;pH 7.4;Product distribution / selectivity;	1 g of <strong>[68302-57-8]amlexanox</strong> was accurately weighed and added to 7 ml of water. The suspension was stirred for 10 minutes. To this suspension 3 ml of 1.0N NaOH was added slowly. The suspension was stirred until the <strong>[68302-57-8]amlexanox</strong> was fully dissolved. The pH of the clear solution was adjusted to 7.4 by adding solid <strong>[68302-57-8]amlexanox</strong>, and diluted to 10 mL by adding water. The excess of <strong>[68302-57-8]amlexanox</strong> was removed by filtration. 400 mL of isopropanol was added slowly while the mixture was vigorously stirred. First crystals of sodium salt appeared while mixture was stirred, and crystallization was complete within 2 hours. The crystalline product was separated by filtration and dried in vacuum.
	With sodium hydroxide; In water;pH 7.6 - 7.8;Product distribution / selectivity;	<strong>[68302-57-8]Amlexanox</strong> was solubilized in NaOH, pH of solution was adjusted to 7.6-7.8 with 1 M Tris, pH 7.4 and desirable volume was adjusted with autoclaved distilled water. Final concentration of NaOH was equimolar to concentration of <strong>[68302-57-8]amlexanox</strong>. Specifically, to make 20 ml of 20 mg/ml <strong>[68302-57-8]amlexanox</strong> solution, 400 mg of <strong>[68302-57-8]amlexanox</strong> were dissolved in 10 ml of 132 mM NaOH and then 5.2 ml of 1 M Tris, pH 7.4 and 4.8 ml of water were added. Solution of <strong>[68302-57-8]amlexanox</strong> was sterilized through 0.2 micrometer filter. Measurement of intrinsic <strong>[68302-57-8]amlexanox</strong> fluorescence confirmed that there was no loss of <strong>[68302-57-8]amlexanox</strong> during filtration.

Reference： [1]Patent: US2007/135473,2007,A1 .Location in patent: Page/Page column 8
[2]Patent: US2007/135473,2007,A1 .Location in patent: Page/Page column 6

9
[ 68302-57-8 ]
[ 68-12-2 ]
(E)-2-(((dimethylamino)methylene)amino)-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With oxalyl dichloride; In dichloromethane; at 20℃; for 16.0h;	To a stirred mixture of <strong>[68302-57-8]amlexanox</strong> (100 mg, 0.34 mmol) and N,N-dimethylformamide (24.5 mg, 0.34 mmol) in anhydrous dichloromethane (10 mL) was added oxalyl chloride (128 mg, 1.0 mmol). The resulting suspension mixture was stirredat room temperature for 16 h. The mixture was concentrated to afford 275 (105 mg, 89%) as a white solid. ?H NMR (400 MHz, DMSO-d6) oe 9.37 (s, 1H), 8.98 (d, J= 1.0 Hz, 1H), 7.96 (d, J 2.2 Hz, 1H), 7.82 (dd, J 8.7, 2.3 Hz, 1H), 7.60 (d, J= 8.6 Hz, 1H), 3.56 (s, 3H), 3.32+(s, 3H), 3.08 (p, J= 6.9 Hz, 1H), 1.26 (d, J= 6.9 Hz, 6H). MS m/z 354.0 (M+1)

Reference： [1]Patent: WO2017/132538,2017,A1 .Location in patent: Page/Page column 168; 169

10
[ 68302-57-8 ]
2-amino-3-(hydroxymethyl)-7-isopropyl-5H-chromeno[2,3-b]pyridin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		To a stirred suspension of <strong>[68302-57-8]amlexanox</strong> (300 mg, 1.0 mmol), N,N-dimethylformamide (8 mg, 0.11 mmol) and dichloromethane (30 mL) was added thionyl chloride (15 mL, 206 mmol) at room temperature. The resulting mixture was refluxed for 5 h and then concentrated to leave 325 mg of an orange solid. A portion (150 mg, 0.47 mmol) was diluted with tetrahydrofuran (20 mL) and the suspension was treated with sodium borohydride (72 mg, 1.9 mmol) and stirredfor 1.5 h at room temperature. The mixture was quenched with water and the resultant clear orange solution was stirred for 10 mm and extracted with dichloromethane (2x). The organic phase was dried (Na2SO4) and concentrated to a solid that was triturated in a small amount of dichloromethane and dried to give 97 (105 mg, 78%) as a light orange solid. ?H NMR (400 MI-Tz, DMSO-d6) oe 8.16 (s, 1H), 7.93 (d, J= 2.3 Hz, 1H), 7.69 (dd, J 8.6, 2.3 Hz, 1H), 7.51(d, J 8.6 Hz, 1H), 7.21 (s, 2H), 5.37 (t, J 5.6 Hz, 1H), 4.47 - 4.36 (m, 2H), 3.05 (p, J= 6.9 Hz, 1H), 1.26 (d, J 6.9 Hz, 6H). MS m/z 285.12 (M+H).

Reference： [1]Patent: WO2017/132538,2017,A1 .Location in patent: Page/Page column 144
[2]Molecular Pharmacology,2018,vol. 94,p. 1210 - 1219

11
[ 68302-57-8 ]
2-amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 100%	With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; for 4.0h;Reflux;	Literature citation for methodology (Ren et al., 2012). To a stirred suspension of 1 (300 mg, 1 mmol) andDMF (8 mg, 0.11 mmol) in DCM (30 mL) was dropwise added thionyl chloride (15 mL, 206mmol) and the resulting mixture was heated at reflux for 4 h. The mixture was concentrated invacuo to afford 2 (325 mg, ~100%) as an orange solid, which was unstable to further purificationand thus used directly in the next step. 1H NMR (400 MHz, DMSO-d6) delta 8.83 (s, 1H), 7.94 (d, J= 2.2 Hz, 1H), 7.77 (dd, J = 8.5, 2.2 Hz, 1H), 7.64 (d, J = 8.6 Hz, 1H), 3.06 (p, J = 7.2 Hz, 1H),1.25 (d, J = 7.0 Hz, 6H).