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CAS No. : | 2484-60-8 | MDL No. : | MFCD01311243 |
Formula : | C9H14O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 186.21 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.78 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.32 |
TPSA : | 63.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 1.68 |
Log Po/w (XLOGP3) : | 1.19 |
Log Po/w (WLOGP) : | 1.05 |
Log Po/w (MLOGP) : | 0.86 |
Log Po/w (SILICOS-IT) : | 0.79 |
Consensus Log Po/w : | 1.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.55 |
Solubility : | 5.29 mg/ml ; 0.0284 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.12 |
Solubility : | 1.41 mg/ml ; 0.00756 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.54 |
Solubility : | 54.1 mg/ml ; 0.29 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.86 |
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 |
---|---|---|
100% | at 100℃; for 1.0h; | A solution of cis-cyclohexane-1,2-dicarboxylic anhydride(7.0 g, 45.5 mmol) in methanol (2 mL, 49.5 mmol) wasstirred at 100C for 1 h. Then, the solvent was evaporated to afford 1 as a white solid which was used in the next stepwithout further purification (8.46 g, 45.5 mmol, 100 %yield). Melting point: 67-69C. IR (KBr): nu 3060, 1710,1670 cm-1. 1H NMR (400 MHz, CDCl3): delta 7.54 (s, 1H),3.68 (s, 3H), 2.89-2.81 (m, 2H), 2.09-1.96 (m, 2H), 1.83-1.72 (m, 2H), 1.61-1.36 (m, 4H). 13C NMR (100 MHz,CDCl3): delta 179.76, 174.06, 51.71, 42.48, 42.33, 26.25, 25.95,23.74, 23.62. HRMS (ESI): calcd. for C9H13O4 [M-H]-185.0792, found 185.0790. |
Reflux; | Step A: Synthesis of Racemic Methyl Hemiester (7?29, 30) [0198] Meso-anhydride (7) was refluxed in MeOH (10 vol. w/v) to obtain racemic mix of hemiesters (29 and 20). Racemic mixture of 29 and 30 (12.08 g) was treated with quinine (21.28 g) in acetone (225 ml) at 55-60 C. and stirred for 30 min. To this clear solution hexane was added (650 ml) and cooled to rt. while stirring for 3 hr. At this stage white solid crashed out of solution. This was filtered and dried to obtain 22 g of the quinine salt (34). The quinine salt was characterized by NMR. [0199] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With quinine; In acetone; at 55 - 60℃;Resolution of racemate; | Step A: Synthesis of Racemic Methyl Hemiester (7?29, 30) [0198] Meso-anhydride (7) was refluxed in MeOH (10 vol. w/v) to obtain racemic mix of hemiesters (29 and 20). Racemic mixture of 29 and 30 (12.08 g) was treated with quinine (21.28 g) in acetone (225 ml) at 55-60 C. and stirred for 30 min. To this clear solution hexane was added (650 ml) and cooled to rt. while stirring for 3 hr. At this stage white solid crashed out of solution. This was filtered and dried to obtain 22 g of the quinine salt (34). The quinine salt was characterized by NMR. [0199]1 g of quinine salt (34) was taken in acetone (20 ml) and heated at 55-60 C. to obtain clear solution and this was cooled to RT while stirring overnight. White solid so obtained was filtered and dried to obtain 490 mg of pure quinine salt of acid isomer 29. The salt was neutralized with 1N HCl to obtain free acid (29) with high chiral purity (99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 2.0h; | To a solution of [7-tert-butyl-5-(4-chloro-3-fluoro-phenyl)furo[3,2-b]pyridin-2-yl]-(2,2- dimethylpiperazin-1-yl)methanone (Hydrochloride salt) (150 mg, 0.312 mmol) in DMF (2 mL) were added <strong>[2484-60-8](cis)-2-methoxycarbonylcyclohexanecarboxylic acid</strong> (69 mg, 0.37 mmol), DIPEA (270 muL, 1.55 mmol) and HATU (142.4 mg, 0.375 mmol). The mixture was stirred at RT for 2h. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with EtOAc/hexanes 0- 60% to obtain methyl (cis)-2-[4-[7-tert-butyl-5-(4-chloro-3-fluoro-phenyl)furo[3,2- b]pyridine-2-carbonyl]-3,3-dimethyl-piperazine-1-carbonyl]cyclohexanecarboxylate (130 mg, 68%) as a white solid. ESI-MS m/z calc.611.2562, found: 612.05. Retention time: 2.23 minutes usinig Method C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium methylate; In methanol; for 5.0h;Inert atmosphere; Reflux; | To a solution of 1 (9.65 g, 51.9 mmol) in dry methanol(20 mL) a 13 % weight sodium methoxide solution in drymethanol (138 mL) was added. The reaction mixture wasstirred at reflux under argon atmosphere for 5 h. Here, thesolvent was evaporated, and 2 N aqueous hydrochloric acidwas added until acidic pH was reached. Then, the aqueousphase was extracted with ethyl acetate (3 x 60 mL). Thecombined organic extracts were dried over magnesium sulfate,filtered, and evaporated to afford 2 as a white solidwhich was used in the next step without further purification(9.07 g, 48.8 mmol, 94 % yield). Melting point: 55-57C.IR (KBr): nu 3020, 1735, 1700 cm-1. 1H NMR (400 MHz,DMSO-d6): delta 12.18 (s, 1H), 3.56 (s, 3H), 2.46-2.32 (m, 2H),2.00-1.85 (m, 2H), 1.75-1.62 (m, 2H), 1.45-1.16 (m, 4H).13C NMR (100 MHz, DMSO-d6): delta 175.87, 175.03, 51.45,44.37, 44.35, 28.64, 28.51, 24.89, 24.78. HRMS (ESI):calcd. for C9H13O4 [M-H]- 185.0792, found 185.0789. |
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