[ CAS No. 25063-68-7 ] {[proInfo.proName]}

Name: 25063-68-7|2,2-Dimethyl-5-((pyridin-3-ylamino)methylene)-1,3-dioxane-4,6-dione|97%
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SKU: A116104
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Quality Control of [ 25063-68-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 25063-68-7 ]

Product Details of [ 25063-68-7 ]

CAS No. :	25063-68-7	MDL No. :	MFCD21606919
Formula :	C₁₂H₁₂N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QZUHCJHZZJYTGE-UHFFFAOYSA-N
M.W :	248.24	Pubchem ID :	91825792
Synonyms :

Calculated chemistry of [ 25063-68-7 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.4
TPSA :	77.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.02
Log Po/w (MLOGP) :	0.41
Log Po/w (SILICOS-IT) :	1.41
Consensus Log Po/w :	1.23

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.36
Solubility :	1.08 mg/ml ; 0.00433 mol/l
Class :	Soluble
Log S (Ali) :	-2.61
Solubility :	0.608 mg/ml ; 0.00245 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.24
Solubility :	0.142 mg/ml ; 0.000571 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.79

Safety of [ 25063-68-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 25063-68-7 ]

* 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.

Upstream synthesis route of [ 25063-68-7 ]
Downstream synthetic route of [ 25063-68-7 ]

[ 25063-68-7 ] Synthesis Path-Upstream 1~3

1
[ 462-08-8 ]
[ 2033-24-1 ]
[ 122-51-0 ]
[ 25063-68-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	at 100℃; for 2 h;	To a preheated (—100 00) mixture of 3-aminopyridine (0.37g, 4.0 mmol) and 2,2-dimethyl-[1 ,3}dioxane-4,6-dione (Meidrum’s acid, 0.69 g, 4.8 mmol) was added triethyl orthoformate (4.0 mL, 24.0 mmol). The solution was stirred at 100 °C for 2 h. The reaction proceeded by changing color from yellow to wine red accompanying the formation of yellow precipitate. After cooling to room temperature, the excess liquid of triethyl orthoformate was removed via vacuumdistillation. The resulting solid was purified via silica gel chromatography using a gradient of 70 to 100percent EtOAc in hexanes.

Reference： [1] Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 763 - 777
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 4, p. 1343 - 1361
[3] Patent: WO2017/31255, 2017, A1, . Location in patent: Paragraph 0086

2
[ 25063-68-7 ]
[ 5423-54-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	at 260℃; for 0.833333 h;	1,5-Naphthyridin-4-ol ZS96. The solution of ZS95 (100 mg, 0.403 mmol) in diphenyl ether (3.0 mL) was refluxed for 50 min on a Bunsen burner. The mixture was then cooled to room temperature and formed precipitate was then filtered and washed with hexane. The crude product was dried, and purified by sublimation at 210 °C and 20 mbar. The yield was 40 mg (68percent). ZS96: white crystals, slowly sublimes at >200 °C. IR (ATR): 3012m, 2925s, 2855s, 2077w, 1975w, 1623s, 1583m, 1559m, 1502s, 1461m, 1421m, 1328w, 1192w, 1137w, 1073w, 977w, 885w, 818w, 779w, 724w, 682w, 590w, 546w, 481w cm^-1. ¹H NMR (500 MHz, CDCl₃+ d-TFA, δ): 9.15 (dd, J₁ = 8.8, J₂ = 1.2, 1H), 9.12-9.10 (m, 1H), 8.51 (d, J = 7.4), 8.41 (dd, J₁ = 8.9, J₂ = 5.4, 1H), 7.19 (d, J = 7.4, 1H). ¹³C NMR (125 MHz, CDCl₃+ d-TFA, δ): 173.25, 147.30, 144.98, 142.03, 131.98, 131.43, 121.01, 116.06. HRMS: m/z 147.05496 corresponds to molecular formula C₈H₆N₂OH⁺(error in ppm -2.22).

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 4, p. 1343 - 1361
[2] European Journal of Medicinal Chemistry, 2019, p. 32 - 50

3
[ 25063-68-7 ]
[ 53454-31-2 ]
[ 5423-54-1 ]

Reference： [1] Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 763 - 777

[ 25063-68-7 ] Synthesis Path-Downstream 1~13

2
[ 462-08-8 ]
[ 2033-24-1 ]
[ 122-51-0 ]
[ 25063-68-7 ]

Yield	Reaction Conditions	Operation in experiment
90%		(0527) A mixture of triethyl orthoformate (1.665 mL, 10.0 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (865 mg, 6.0 mmol) was heated at 90C for 1.5 h and then cooled to 70C. 3-amino- pyridine 15 (471 mg, 5.0 mol) was slowly added over 10 min with an EtOH (20 mL) rinse while maintaining the reaction temperature between 60 and 70C. The reaction was then heated for an additional 30 min and allowed to cool to RT. The precipitate was filtered, washed with EtOH (20 mL), and dried to yield compound as a light-yellow solid (1118mg, 90%). 1H NMR (400 MHz, chloroform-i delta 1 1.25 (d, J= 14.2 Hz, 1H), 8.66 - 8.59 (m, 2H), 8.55 (dd, J= 4.8, 1.4 Hz, 1H), 7.61 (ddd, J= 8.3, 2.8, 1.4 Hz, 1H), 7.41 (dd, J = 8.3, 4.7 Hz, 1H), 1.77 (s, 6H).
72%	at 100℃; for 2h;	To a preheated (-100 00) mixture of 3-aminopyridine (0.37g, 4.0 mmol) and 2,2-dimethyl-[1 ,3}dioxane-4,6-dione (Meidrum?s acid, 0.69 g, 4.8 mmol) was added triethyl orthoformate (4.0 mL, 24.0 mmol). The solution was stirred at 100 C for 2 h. The reaction proceeded by changing color from yellow to wine red accompanying the formation of yellow precipitate. After cooling to room temperature, the excess liquid of triethyl orthoformate was removed via vacuumdistillation. The resulting solid was purified via silica gel chromatography using a gradient of 70 to 100% EtOAc in hexanes.
65%	In ethanol; at 100℃;	Meldrum?s acid (1.50 g, 10.4 mmol) was dissolved in EtOH (24 mL), and 3-aminopyridine (0.89 g, 9.5 mmol) was added to the solution followed by triethyl orthoformate (1.40 g, 9.45 mmol). The mixture was stirred with heating at 100 C until ethanol evaporated. The solid residue was dissolved in a minimal amount of hot EtOH, charcoal was added, and the suspension was heated to boiling and quickly filtered through warm Cellite. The quickly formed crystals were filtered and washed with a small amount of EtOH. The yield was 1.53 g (65%). ZS95: off-white powder, mp 135 C. IR (ATR): 3236w, 3206w, 3074w, 2993w, 2946w, 1726m, 1686s, 1619s, 1579m, 1480m, 1454w, 1413s, 1380m, 1325m, 1284m, 1262m, 1222m, 1144w, 1022w, 1000w, 936w, 847w, 822w, 803m, 778w, 726w, 704w, 654w, 604w, 507w cm-1. 1H NMR (500 MHz, CDCl3, delta): 11.26 (d, J = 13.4, H-N, exchangeable with D2O), 8.64 (d, J = 14.2, 1H), 8.63-8.61 (m, 1H), 8.56-8.54 (m, 1H), 7.66-7.62 (m, 1H), 7.43-7.39 (m, 1H), 1.77 (s, 6H). 13C NMR (125 MHz, CDCl3, delta): 165.41, 163.04, 152.74, 147.86, 140.51, 134.55, 124.68, 124.25, 105.44, 88.71, 27.06. HRMS: m/z 249.08686 corresponds to molecular formula C12H12N2O4H+ (error in ppm -0.48).

Reference： [1]Patent: WO2019/89648,2019,A1 .Location in patent: Page/Page column 67
[2]Journal of the American Chemical Society,2009,vol. 131,p. 763 - 777
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 1343 - 1361
[4]Patent: WO2017/31255,2017,A1 .Location in patent: Paragraph 0086
[5]European Journal of Medicinal Chemistry,2019,vol. 162,p. 32 - 50

3
[ 25063-68-7 ]
[ 53454-31-2 ]
[ 5423-54-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 763 - 777

4
[ 25063-68-7 ]
[ 5423-54-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	In diphenylether; at 260℃; for 0.833333h;	1,5-Naphthyridin-4-ol ZS96. The solution of ZS95 (100 mg, 0.403 mmol) in diphenyl ether (3.0 mL) was refluxed for 50 min on a Bunsen burner. The mixture was then cooled to room temperature and formed precipitate was then filtered and washed with hexane. The crude product was dried, and purified by sublimation at 210 C and 20 mbar. The yield was 40 mg (68%). ZS96: white crystals, slowly sublimes at >200 C. IR (ATR): 3012m, 2925s, 2855s, 2077w, 1975w, 1623s, 1583m, 1559m, 1502s, 1461m, 1421m, 1328w, 1192w, 1137w, 1073w, 977w, 885w, 818w, 779w, 724w, 682w, 590w, 546w, 481w cm-1. 1H NMR (500 MHz, CDCl3 + d-TFA, delta): 9.15 (dd, J1 = 8.8, J2 = 1.2, 1H), 9.12-9.10 (m, 1H), 8.51 (d, J = 7.4), 8.41 (dd, J1 = 8.9, J2 = 5.4, 1H), 7.19 (d, J = 7.4, 1H). 13C NMR (125 MHz, CDCl3 + d-TFA, delta): 173.25, 147.30, 144.98, 142.03, 131.98, 131.43, 121.01, 116.06. HRMS: m/z 147.05496 corresponds to molecular formula C8H6N2OH+ (error in ppm -2.22).
	With diphenylether; at 215℃; for 4h;	(0528) Intermediate 112 (300 mg, 1.21 mmol) was added portion wise to diphenyl ether (100 ml, 630 mmol) at 215C. The solution was stirred at reflux for 4h and then cooled to room temperature. The combined precipitated solid were filtered off and washed with diethyl ether (2 x 500 ml) to give a pale brown solid. The solid was triturated in diethyl ether (2 x 500 ml), filtered off and dried under vacuum to give of intermediate 2, that was used without further purification for the next step. (78 mg, 44% yeild). 1H NMR (400 MHz, Methanol-i 4) delta 8.75 (dd, J= 4.3, 1.5 Hz, 1H), 8.15- 8.01 (m, 2H), 7.74 (dd, J= 8.6, 4.2 Hz, 1H), 6.52 (d, J= 7.4 Hz, 1H).

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1343 - 1361
[2]European Journal of Medicinal Chemistry,2019,vol. 162,p. 32 - 50
[3]Patent: WO2019/89648,2019,A1 .Location in patent: Page/Page column 68

5
[ 25063-68-7 ]
[ 7689-63-6 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1343 - 1361
[2]European Journal of Medicinal Chemistry,2019,vol. 162,p. 32 - 50
[3]Patent: WO2019/89648,2019,A1

6
[ 25063-68-7 ]
4-((4-methoxybenzyl)thio)-1,5-naphthyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1343 - 1361
[2]Patent: WO2017/31255,2017,A1

7
[ 25063-68-7 ]
[ 79425-89-1 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1343 - 1361
[2]Patent: WO2017/31255,2017,A1

8
[ 25063-68-7 ]
[ 16795-72-5 ]