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CAS No. : | 741687-07-0 | MDL No. : | MFCD12408566 |
Formula : | C12H24N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJKGQHBSAKUVNM-UHFFFAOYSA-N |
M.W : | 228.33 g/mol | Pubchem ID : | 45095672 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.92 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 68.95 |
TPSA : | 55.56 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) : | -6.67 cm/s |
Log Po/w (iLOGP) : | 2.87 |
Log Po/w (XLOGP3) : | 1.44 |
Log Po/w (WLOGP) : | 1.74 |
Log Po/w (MLOGP) : | 1.44 |
Log Po/w (SILICOS-IT) : | 1.19 |
Consensus Log Po/w : | 1.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.9 |
Solubility : | 2.88 mg/ml ; 0.0126 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.21 |
Solubility : | 1.4 mg/ml ; 0.00613 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.93 |
Solubility : | 2.66 mg/ml ; 0.0117 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-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 potassium trimethylsilonate; In tetrahydrofuran; at 18 - 25℃; for 18h; | Step B. To a solution of the above solid from step A (3.28g) in THF (50ml) was addedpotassium trimethylsilanolate (3.68g) and the resulting mixture was stirred at roomtemperature for 18 hours. The reaction mixture was partitioned between dichloromethane andsaturated sodium bicarbonate. The organic extracts were dried (MgSO4) and evaporated todryness to give the sub-title compound (2.42g) as an orange oil which was used withoutfurther purification. NMR(d6 DMSO): 0.75 (t, 3H), 1.1-1.4 (m, 6H), 1.3 (s, 9H), 3.1 (m, 2H),3.45(m,2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2: Preparation offers-butyl 4-ethyl-4-([4-(methylsulfonyl)benzyl]amino}carbonyl)piperidine-1 -carboxylate; .To a solution of [4-(methylsulfonyl)phenyl]acetic acid (395mg) in dichloromethane(20ml) was added disopropyldiethylamine (0.38ml) followed by HATU (VOOmg) and mixturewas stirred for 10 minutes before the addition of tert-butyl 4-amino-4-ethylpiperidine-l-carboxylate (420mg). The resulting mixture was stirred at room temperature for 18 hours. Thereaction mixture was partitioned between dichloromethane and water. The organic extractswere dried (MgSCU) and evaporated to dryness. The residue was purified chromatography onsilica eluting with gradient of ethyl acetate and isohexane to give the sub-title compound asan oil (750mg). NMR (CDC13): 0.9 (t, 3H), 1.5 (s, 9H), 1.5 (m, 2H), 1.9 (m, 2H), 2.1 (m, 2H),3.0 (m, 2H), 3.1 (s, 3H), 3.7 (s, 2H), 3.8 (m, 2H), 5.2 (s, 1H), 7.6 9d, 2H), 8.0 (d, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 7: tert-hutyl 4-ethyl-4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin- 4( l/f,3/f,5H)-yl)piperidine- 1 -carboxylate[0168] 1 -tert-QvXy 4-methyl 3-formyl- lH-pyrrolo[2,3-delta]pyridine- 1 ,4-dicarboxylate (211 mg, 0.692 mmol) was dissolved in MeOH (10 mL) and tert-hvXy 4-amino-4- ethylpiperidine-1 -carboxylate (158 mg, 0.692 mmol) were added followed by 2 drops of acetic acid. The solution was allowed to stir at room temperature for 2 h. Then sodium cyanoborohydride (44 mg, 0.692 mmol) was added over the course of 6 h at room temperature. The solution was quenched with water and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated in vacuo. Purification by silica gel chromatography (70% EtOAc/Hexanes) gave 127 mg of l-tert-buty 4-methyl 3-((l -(tert- butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)- lH-pyrrolo[2,3-delta]pyridine- 1 ,A- dicarboxylate. [M+H] found 417.[0169] 1 -tert-BvXy 4-methyl 3 -(( 1 -(tert-butoxycarbonyl)-4-ethylpiperidin-4- ylamino)methyl)-lH-pyrrolo[2,3-delta]pyridine-l,4-dicarboxylate (123 mg, 0.238 mmol) was stirred in MeOH (3 mL), IN NaOH (3 mL), and THF (2 mL) for 16 h. The mixture was concentrated in vacuo. Purification via basic prep HPLC 20% to 50% B in A gave 60 mg of 3-((l-(fert-butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-lH-pyrrolo[2,3-6]pyridine-4-carboxylic acid. 1U NMR (400 MHz, CD3OD) delta 8.29 (d, IH, J= 4.8 Hz),7.68 (s, IH), 7.52 (d, IH, J= 5.1 Hz), 4.31 (s, 2H), 3.95-4.01 (m, IH), 2.03 (q, 2H, J= 7.6Hz), 1.92-1.94 (m, 4H), 1.47 (s, 9H), 1.46 (m, 2H), 1.07 (t, IH, J= 7.3 Hz). [M+H] found403.[0170] 3-((l-(tert-Butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-l/-f-pyrrolo[2,3-6]pyridine-4-carboxylic acid (50 mg, 0.124 mmol), HATU (94 mg, 0.248 mmol), and A- dimethylaminopyridine (46 mg, 0.373 mmol) were stirred in DMF (3 mL) at room temperature for 1 h. The solution was concentrated in vacuo to give the title compound which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; potassium hydroxide; In acetonitrile; at 20℃; | To a solution of the compound 3 (20.5 g, 80 rnmoi) in CH3CN (200 ml) and 5N KOH (10() nil) was added i,3-dibromo-5,5-dimethylimidazohdine-2,4-diorie (11.1 g, 40nunol). The mixture was stirred overnight at room temperature. Afier completion, the mixture was concentrated to remove CH3CN. Adjustment of the pH of the water phase to 5 was with 2N HC1 in ice bath, the mixture was extracted with EA and separated i1en adjustment of the pH of water phase to 10. The precipitate was collected to afford the compound 4 (10 g, 55%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos; In toluene; at 100℃; | A. solution of the compound 4 (1.0 g, 4.4 mmoi). ethyl 4-bromobenzoar.e (943 nig, 4.4 mmol), Pd2(dba)3 (202 mg, 0.22 mmol), Ruphos (103 mg, 0.22 nunol) arid Cs2CO3 (2.9 g, 8.8 inmol) in toluene (25 in) was stirred at 100C overnight. The mixture was concentrated and purified by silica gel column with EA:PE = 1:5 to affbrd compound 5 (1.0 g, 59%) as a light yellow solid. |
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