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CAS No. : | 150054-50-5 | MDL No. : | MFCD09859804 |
Formula : | C8H10ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CQKHUAFREIMBJI-UHFFFAOYSA-N |
M.W : | 171.62 | Pubchem ID : | 9795246 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.31 |
TPSA : | 33.12 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) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 1.93 |
Log Po/w (XLOGP3) : | 1.36 |
Log Po/w (WLOGP) : | 1.69 |
Log Po/w (MLOGP) : | 1.14 |
Log Po/w (SILICOS-IT) : | 2.72 |
Consensus Log Po/w : | 1.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.1 |
Solubility : | 1.37 mg/ml ; 0.00797 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.66 |
Solubility : | 3.77 mg/ml ; 0.022 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.24 |
Solubility : | 0.0988 mg/ml ; 0.000575 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.7 |
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 |
---|---|---|
55% | With sodium methylate In <i>N</i>-methyl-acetamide; methanol; water | EXAMPLE 8 Synthesis 2-hydroxymethyl-4-Methoxy-3,5-Lutidine In a round bottom flask equipped with a stirrer, a condenser and a nitrogen bubbler, 4-Chloro-2-hydroxymethyl-3,5-Lutidine (1 eq.) was dissolved in Dimethylformamide (3-9 volumes) and Methanol (1.5-4.5 volumes). Sodium methoxide (4 eq.) was added and the temperature was raised to (95-100.image. C.). At the end of the reaction the solvent was distilled under vacuum. Water (2 volumes) was added to the residue and the product was extracted with dichloromethane (2*4 volumes). The combined organic extracts were dried over sodium sulfate, filtered and evaporated. The crude product, 2-hydroxymethyl-4-Methoxy-3,5-lutidine, was obtained in 55percent yield. In another work-up method, after evaporation of the dimethylformamide/methanol, water (2 volumes was added to the residue and the product was extracted with toluene (3*4 volumes). The organic extracts were combined and while cooling and stirring HCl gas (1.2 eq.) was bubbled into solution. The product 2-hydroxymethyl-4-Methoxy-3,5-lutidine hydrochloride salt was filtered and washed with toluene. The crude product was obtained as a white solid in 50percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: at 60 - 95℃; for 7 h; Stage #2: With sodium hydroxide In water; toluene at 50℃; for 18 h; |
At 90-95 0C, a solution of 4-chloro-2,3,5-trimethylpyridine-Λ/-oxide (60.0 g, 350 mmol) in toluene (920 mL), which was kept at about 60 0C, was added over 7 h to acetic anhydride (232 mL). Under vacuum at about 60 0C, the reaction mixture was concentrated until 820 mL had been distilled off. Toluene (840 mL) was added and, again, solvents were distilled off (940 mL). Then, toluene (180 mL) and 40percent aqueous NaOH (80 mL) were added before the reaction mixture was heated at 50 0C for about 15 h. After addition of saturated aqueous sodium bicarbonate (120 mL), the phases were separated and the aqueous layer was extracted once more with toluene (80 mL). Finally, the combined organic phase was washed with saturated aqueous sodium bicarbonate (120 mL) and evaporated to dryness to give 4-chloro-2-hydroxymethyl-3,5-dimethylpyridine as a brownish oil which solidified upon standing; yield 61.8 g (quantitative).1H-NMR (200 MHz, DMSO-d6): δ= 2.30 (s, 3H), 2.36 (s, 3H), 4.58 (br s, 2H), 5.11 (br s, 1H), 8.27 (s, 1 H); LC-MS: MH+ = 172/174. |
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