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CAS No. : | 479028-72-3 | MDL No. : | MFCD09834780 |
Formula : | C8H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IAXRYEXXAPLEGT-UHFFFAOYSA-N |
M.W : | 162.15 | Pubchem ID : | 18983819 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.15 |
TPSA : | 54.6 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) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 1.11 |
Log Po/w (XLOGP3) : | 1.62 |
Log Po/w (WLOGP) : | 1.03 |
Log Po/w (MLOGP) : | 0.32 |
Log Po/w (SILICOS-IT) : | 0.29 |
Consensus Log Po/w : | 0.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -2.35 |
Solubility : | 0.716 mg/ml ; 0.00442 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.38 |
Solubility : | 0.678 mg/ml ; 0.00418 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.45 |
Solubility : | 5.77 mg/ml ; 0.0356 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.65 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In ISOPROPYLAMIDE; toluene; acetonitrile at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With palladium 10% on activated carbon; hydrogen; sodium hydroxide In ethanol; water at 50℃; Flow reactor; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 30℃; for 48h; | 146 Example 146 : N-(5-((5-methyl-8-(2-oxopyrrolidin- l-yl)-5H-chromeno [4,3-c] pyridin-3- yl)amino)pyridin-3-yl)imidazo[l,2-a]pyridine-5-carboxamide A mixture of l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.16 mmol, HC1 salt), imidazo[l,2-a]pyridine-5- carboxylic acid (38 mg, 0.23 mmol) and EDCI.HC1 (45 mg, 0.23 mmol) in pyridine (2 mL) was heated at 30 °C for 48 h. A brown suspension was formed. LCMS (Rt = 0.652 min; MS Calcd: 531.2; MS Found: 532.1 [M+H]+). The mixture was concentrated and the residue was poured into water (20 mL) and stirred for 2 minutes. The aqueous layer was extracted with ethyl acetate (20 mL x3).The combined organic layer was washed with water (20 mL x2) and brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by prep-TLC (DCM/MeOH, 10/1) then further purified by prep-HPLC (0.05% NH3.H2O as an additive) and lyophilized to giveN-(5-((5-methyl-8-(2-oxopyrrolidin-l-yl)-5H- chromeno[4,3-c]pyridin-3-yl)amino)pyridin-3-yl)imidazo[l,2-a]pyridine-5-carboxamide (5.8 mg, yield: 7%) as a yellow solid. NMR (400 MHz DMSO-rie) d 1.56 (3H, d, J= 6.5 Hz), 2.02-2.10 (2H, m), 2.52-2.54 (2H, m, overlapped with the peak of DMSO), 3.85 (2H, t, J= 7.8 Hz), 5.29 (1H, q , J= 6.5 Hz), 6.79 (1H, s), 7.33 (1H, dd, J= 8.5, 2.3 Hz), 7.40-7.47 (2H, m), 7.69 (1H, d , J= 7.3 Hz), 7.74 (1H, s), 7.86-7.91 (2H, m), 8.48-8.52 (2H, m), 8.67-8.75 (3H, m), 9.57 (1H, brs), 10.94 (1H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.7% | With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Cooling with ice; Inert atmosphere; | Imidazo[1,2]pyridin-5-ylmethanol Dissolve imidazo[1,2]pyridine-5-carboxylic acid (100mg, 0.62mmol) in tetrahydrofuran (5ml), add lithium aluminum hydride (35mg, 0.93mmol) under ice bath, protect with argon, and react at room temperature 2 After hours, add 15ml of water and 15ml of 15% sodium hydroxide solution to the reaction solution for quenching, extract with dichloromethane (20ml*3 times) and combine the organic phases, then wash with saturated brine (15ml*1 times) . The organic phase was dried and concentrated, and 45 mg of the title compound was obtained by column separation. The yield was 48.7%. |