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CAS No. : | 588720-29-0 | MDL No. : | MFCD11870763 |
Formula : | C8H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GMBMIWBXIHLWDP-UHFFFAOYSA-N |
M.W : | 162.15 | Pubchem ID : | 12132799 |
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) : | -6.31 cm/s |
Log Po/w (iLOGP) : | 1.1 |
Log Po/w (XLOGP3) : | 1.38 |
Log Po/w (WLOGP) : | 1.03 |
Log Po/w (MLOGP) : | 0.32 |
Log Po/w (SILICOS-IT) : | 0.29 |
Consensus Log Po/w : | 0.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.2 |
Solubility : | 1.01 mg/ml ; 0.00626 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.13 |
Solubility : | 1.2 mg/ml ; 0.00742 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 : | 1.4 |
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: |
* 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 N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 3h; | [1145] A flask is charged with <strong>[588720-29-0]imidazo[1,5-a]pyridine-7-carboxylic acid</strong> (4.3 g, 19.9 mmol), (3R)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride (3.6 g, 18.2 mmol), DIEA (19 ml, 109 mmol), and DMF (200 ml). The reaction mixture is cooled to 0 C. and HATU (6.9 g, 18.2 mmol) is added to it. The mixture is allowed to stir at rt for 3 h. The mixture is diluted with MeOH (20 ml) and DOWEX 50WX2-40 ion exchange resin (2 g) is added; the mixture is adjetated in a water bath (35-40 C.) for 20 min, is filtered, and the resin washed with 3 portions of MeOH. The product is liberated from the resin by treatment with a solution of 20% NH4OH/MeOH. The basic alcohol washes are concentrated in vacuo to give a brown oil, which is purified by silica gel chromatography (10% MeOH/79% CH2Cl2/1% NH3OH) to give a yellow solid. The resulting solid is dissolved in MeOH (2 ml) and a solution of d-tartaric acid (0.151 g, 1.0 mmol) in MeOH (3.0 ml) is added to it. The solvent is removed under vacuum to give a yellow solid (0.49 g, 1.0 mmol). HRMS (FAB) calcd for C15H18N4O+H 271.1559, found 271.1560. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride; water; for 3h;Heating / reflux; | [1143] Methylimidazo[1,2-a]pyridin-6-carboxylate (3.2 g, 18.0 mmol) is dissolved in 3N HCl (200 ml) and heated under reflux for 3 h. The solvent is removed under vacuum and the resulting brown solid is recrystallized from H2O/EtOH/Et2O to afford a light brown solid (4.3 g, 21.6 mmol, 119%) for imidazo[1,5-a]pyridine-7-carboxylic acid. HRMS (FAB) calcd for C8H6N2O2+H 163.0508, found 163.0489. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | To a 50 mL single neck RB flask starting 1H-Imidazol (1,5-a)pyridine-7-carboxylic acid (0.5 g, 3.086 mmol) was added, followed by ethyl ester of L-Leucine Hydrochloride (0.5 g, 3.086 mmol), HATU (0.323 g, 0.85 mmol) and DMF (8 mL). The contents were stirred for 5 mins. After clear solution formation DIPEA (1.1 mL, 6.172 mmol) was added and the reaction mass stirred for 16h at 20-30C. After 16h, the completion of the reaction was confirmed byTLC/LCMS, and worked-up. Ice-cold water (2OmL) was added slowly to the reaction mixture with stirring. The product was extracted with ethyl acetate (2x2OmL). The ethyl acetate extracts were separated washed with (1x20 mL) water, separated the organics, dried over anhydrous sodium sulphate and distilled off the volatiles under reduced pressure to get the crude product. This crude material was subjected to purification using preparative RP HPLC. The pure material thus obtained yielded 60-70% yield of the product of desired purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In ethyl acetate; at 20℃; for 1h;Inert atmosphere; | General procedure: To a solution of 2-methyl-3-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine, Intermediate 1, (150 mg, 0.7 mmol) in dichloromethane (DCM) (5.0 mL) was added HATU (348 mg, 0.91 mmol), followed by DIPEA (0.6 mL, 3.5 mmol) and 1-naphthoic acid (222 mg, 1.3 mmol), and the mixture stirred at room temperature for 1 h. The reaction mixture was diluted with water and the aqueous layer extracted with DCM (*2). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase HPLC (Method A) to afford the title compound as a white solid (94 mg, 36% yield). MS (ESI): mass calcd. for C24H21N3O, 367.1; m/z found, 368.1 [M+H]+. 1H NMR (400 MHz, Methanol-d4) delta 8.12-7.93 (m, 2H), 7.89-7.74 (m, 1H), 7.67-7.35 (m, 9H), 5.20-4.92 (m, 2H), 4.46-4.22 (m, 1H), 4.13-3.98 (m, 0.3H), 3.76 (d, J=54.9 Hz, 3H), 3.52-3.41 (m, 1H), 2.93-2.75 (m, 0.7H), 2.57-2.30 (m, 1H). |
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