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CAS No. : | 875318-46-0 | MDL No. : | MFCD09991532 |
Formula : | C13H19N3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NPJBMYLMWPCRIY-UHFFFAOYSA-N |
M.W : | 265.31 | Pubchem ID : | 53487067 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 73.54 |
TPSA : | 75.55 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.25 cm/s |
Log Po/w (iLOGP) : | 2.58 |
Log Po/w (XLOGP3) : | 0.94 |
Log Po/w (WLOGP) : | 0.48 |
Log Po/w (MLOGP) : | 0.71 |
Log Po/w (SILICOS-IT) : | 1.15 |
Consensus Log Po/w : | 1.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.98 |
Solubility : | 2.77 mg/ml ; 0.0105 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.11 |
Solubility : | 2.04 mg/ml ; 0.00771 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.46 |
Solubility : | 0.92 mg/ml ; 0.00347 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.64 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
99% | Stage #1: With potassium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667 h; Stage #2: for 0.333333 h; |
Stage 1 - Coupling; Piperidin-4yl-methanol (2.48g, 21.55mmol) was stirred in 1 :1 DMF/MeCN (2OmL) with K2CO3 (8.9g, 64.65mmol) for 10 minutes at RT under a nitrogen atmosphere. Intermediate F (5g, 21.55mmol) was then added and the reaction allowed to stir for 20 minutes. It was then diluted with H2O (10OmL) and extracted with EtOAc (2 x 10OmL). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give the product as an orange solid which was used in the next step without further purification (5.7Og, 99percent). m/z = 266 [M+H]+. |
54% | With potassium carbonate In acetonitrile at 10 - 20℃; for 4 h; | A solution of 2-(methylsulfonyl)- 5-pyrimidinecarboxylic acid, ethyl ester (0.094 mol)in acetonitrile (40ml) was added at 10°C to a suspension of 4-piperidinemethanol(0.086 mol) and potassium carbonate (0.172 mol) in acetonitrile (200ml) under N2flow. The mixture was brought to room temperature, then stirred for 4 hours, pouredout into water and extracted with EtOAc. The organic layer was separated, dried(MgSO4), filtered, and the solvent was evaporated. The residue (23 g) was crystallizedfrom acetonitrile/diethyl ether. The precipitate was filtered off and dried, yielding 7.8g(34percent) of intermediate 8. The mother layer was evaporated. The residue (17g) waspurified by column chromatography over silica gel (20-45um) (eluent:DCM/MeOH/NH4OH 97/3/0.1). The pure fractions were collected and the solvent wasevaporated, yielding 4.6g (20percent) of intermediate 8, melting point 129°C. |
20% | With potassium carbonate In acetonitrile at 10 - 20℃; for 4 h; | a) Preparation of intermediate 3 A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid ethyl ester (0.094 mol) in acetonitrile (40ml) was added at 1O0C to a suspension of 4-piperidinemethanol (0.086 mol) and K2CO3 (0.172 mol) in acetonitrile (200ml) under N2 flow. The mixture was brought to room temperature, then stirred for 4 hours, poured into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (23 g) was crystallized from acetonitrile/diethyl ether. The mother layer was evaporated and the obtained residue was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 97/3/0.1; 20-45μm). The pure fractions were collected and the solvent was evaporated, yielding 4.6g (20percent) (M.P.: 129°C) of intermediate 3. |
20% | With potassium carbonate In acetonitrile at 10 - 20℃; for 4 h; | a) Preparation of intermediate 7 A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.094 mol) in acetonitrile (40ml) was added at 100C to a suspension of 4-piperidinemethanol (0.086 mol) and potassium carbonate (0.172 mol) in acetonitrile (200ml) under N2 flow. The mixture was brought to room temperature, then stirred for 4 hours, poured out into water and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (23g) was crystallized from CHβCN/diethyl ether. The precipitate was filtered off and dried, yielding 7.8g (34percent) of intermediate 7. The residue was purified by column chromatography over silica gel (20-45 μm) (eluent: DCM/MeOH/NH4OH 97/3/0.1). The pure fractions were collected and the solvent was evaporated, yielding 4.6g (20percent) of intermediate 7, melting point 129°C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2.5 h; | Step 18a: Ethyl 2-(4-hydroxypiperidin-l-yl)pyrimidine-5-carboxylate (Compound 0701)A mixture of compound 0605 (900 mg, 4.84 mmol), piperidin-4-ylmethanol (0.56 g, 4.86 mmol) and potassium carbonate (330 mg, 2.39 mmol) in DMF (2 mL) was stirred at ambient temperature for 2.5 h. The DMF was removed under reduced pressure and the residue was poured into brine, filtered to obtain the product 0701 (1.20 g, 95 percent) as a yellow solid: LCMS: 266 [M+ 1]+. 1H NMR (400 MHz, DMSO- dβ) δ 1.10 (m, 2H), 1.29 (t, J= 7.2 Hz, 3H), 1.72 (m, 3H), 2.97 (m, 2H), 3.27 (m, 2H), 4.26 (q, J= 7.2 Hz, 2H), 4.75 (m, 2H), 8.76 (m, 2H). |
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