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CAS No. : | 90418-64-7 | MDL No. : | MFCD13179643 |
Formula : | C9H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BWIFRKKQXKCKQQ-UHFFFAOYSA-N |
M.W : | 174.16 | Pubchem ID : | 18663323 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.5 |
TPSA : | 63.08 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.84 cm/s |
Log Po/w (iLOGP) : | 1.05 |
Log Po/w (XLOGP3) : | 0.73 |
Log Po/w (WLOGP) : | 1.33 |
Log Po/w (MLOGP) : | -0.65 |
Log Po/w (SILICOS-IT) : | 1.3 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -1.88 |
Solubility : | 2.28 mg/ml ; 0.0131 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.63 |
Solubility : | 4.05 mg/ml ; 0.0233 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.7 |
Solubility : | 0.349 mg/ml ; 0.002 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Ethyl-1.5-naphthyridin, wss.KMnO4 (70grad); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | Stage #1: 1,5-naphthyridine-3-carboxylic acid With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0℃; for 0.25h; Stage #2: 4-(4-ethylpiperazin-1-yl)-3-fluoroaniline In ethyl acetate at 0 - 20℃; for 16h; | 16 Example 16 Compound 15: N-(4-(4-ethylpiperazin-1-yl)-3-fluorophenyl)-1,5-naphthyridine-3-carboxamide T3P 50% solution in EtOAc (5 mL) was added to a stirred solution of 1,5- naphthyridine-3-carboxylic acid (0.102 g, 0.58 mmol) in pyridine (2 mL) at 0°C and the mixture was stirred for 15 min. Then 4-(4-ethylpiperazin-1-yl)-3-fluoroaniline (0.130 g, 0.58 mmol) was added to the reaction mixture at 0°C. The reaction mixture was stirred at rt for 16 hrs. After completion of the reaction, the reaction mixture was passed through the filter column over neutral alumina twice to remove the excess of T3P. The crude product was purified by prep-HPLC and the fractions were concentrated to minimum volume, filtered through 0.4 µ syringe filter and lyophilized to afford 0.032 g of Compound 15 as an off-white solid in 15% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,5-naphthyridine-3-carboxylic acid With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0℃; for 0.25h; Stage #2: 4-((4-(2-methoxyethyl)-1,4-diazepan-1-yl)sulfonyl)benzene-1,2-diamine In ethyl acetate at 0 - 20℃; for 16h; | 15 Example 15 Compound 14: 3-(6-( 2-methoxyethyl)-1,4-diazepan-1-ylsulfonyl)-1H-benzo[d]imidazol-2- yl)-1,5-naphthyridine T3P 50% solution in EtOAc (5 mL) was added to a stirred solution of 1,5- naphthyridine-3-carboxylic acid (0.25 g, 1.43 mmol) in pyridine (2 mL) at 0°C, and the reaction mixture was stirred for 15 min. Then Int-11 (0.47 g, 1.43 mmol) was added to the reaction mixture at 0°C. The reaction mixture was stirred at rt for 16 hrs. After completion of the reaction, the reaction mixture was passed through the filter column over neutral alumina twice to remove the excess of T3P to afford 0.3 g of crude N-(2-amino-4-(4-(2-methoxyethyl)-1,4-diazepan-1- ylsulfonyl)phenyl)-1,5-naphthyridine-3-carboxamide as a brown solid. The solid was dissolved in 15 mL of acetic acid and 10 mL of xylene was added. The reaction mixture was heated at 100°C for 3 hrs. After completion of the reaction, the mixture was diluted with water (15 mL) and extracted with EtOAc (2 x 50 mL). Combined organic layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resultant crude product was purified by prep-HPLC column chromatography to afford 38 mg of Compound 14 as an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.25 g | Stage #1: 1,5-naphthyridine-3-carboxylic acid With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0℃; for 0.25h; Stage #2: C15H26N4O3S In ethyl acetate at 0 - 20℃; for 16h; | 14 Example 14 Compound 13: 3-(5-(4-(2-methoxyethyl)-1,4-diazepan-1-ylsulfonyl)-1-methyl-1H-benzo[d]- imidazol-2-yl)-1,5-naphthyridine T3P 50% solution in EtOAc (5 mL) was added to a stirred solution of 1,5- naphthyridine-3-carboxylic acid (0.25 g, 1.43 mmol) in pyridine (2 mL) at 0°C, and the reaction mixture was stirred for 15 min. Then Int-14 (0.48 g, 1.43 mmol) was added to the reaction mixture at 0 °C, and it was stirred at rt for 16 hrs. After completion of the reaction, the reaction mixture was passed through the filter column over neutral alumina twice to remove the excess of T3P to give 0.25 g N-(2-amino-4-(4-(2-methoxyethyl)-1,4-diazepan-1-ylsulfonyl)phenyl)-N-methyl-1,5- naphthyridine-3-carboxamide as a brown solid. The solid was dissolved in 15 mL of acetic acid and 10 mL of xylene was added. The reaction mixture was heated at 100°C for 3 hrs. After completion of the reaction, the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL). Combined organic layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resultant crude compound was purified by prep-HPLC method to afford 61 mg of Compound 13 as an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,5-naphthyridine-3-carboxylic acid With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0℃; for 0.25h; Stage #2: 4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)benzene-1,2-diamine In ethyl acetate at 0 - 20℃; for 16h; | 13 Example 13 Compound 12: N-(2-amino-4-(4-methyl-1,4-diazepan-1-ylsulfonyl)phenyl)-1,5-naphthyridine - 3-carboxamide T3P 50% solution in EtOAc (5 mL) was added to a stirred solution of 1,5- naphthyridine-3-carboxylic acid (0.25 g, 1.43 mmol) in pyridine (2 mL) at 0 °C, and the mixture was stirred for 15 min. Then Int-16 (0.405 g, 1.43 mmol) was added to the reaction mixture at 0°C. The reaction mixture was stirred at rt for 16 hrs. After completion of the reaction, the reaction mixture was passed through the filter column over neutral alumina twice to remove the excess of T3P to afford 300 mg of crude N-(2-amino-4-(4-methyl-1,4-diazepan-1- ylsulfonyl)phenyl)-1,5-naphthyridine-3-carboxamide as a brown solid. The solid was dissolved in 15 mL of acetic acid, 10 mL of xylene was added, and the mixture was heated at 100°C for 3 hrs. After completion of the reaction, the mixture was diluted with water (25 mL) and extracted with EtOAc (2 x 50 mL). Combined organic layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resultant crude compound was purified by prep-HPLC to afford 38 mg of Compound 12 as an off-white solid. |
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