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CAS No. : | 113293-71-3 | MDL No. : | MFCD06659089 |
Formula : | C6H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TXPRFSOGPYITOT-UHFFFAOYSA-N |
M.W : | 124.14 | Pubchem ID : | 2794829 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 34.77 |
TPSA : | 59.14 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) : | -7.22 cm/s |
Log Po/w (iLOGP) : | 1.03 |
Log Po/w (XLOGP3) : | -0.23 |
Log Po/w (WLOGP) : | 0.01 |
Log Po/w (MLOGP) : | -0.34 |
Log Po/w (SILICOS-IT) : | 0.49 |
Consensus Log Po/w : | 0.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.89 |
Solubility : | 15.9 mg/ml ; 0.128 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.55 |
Solubility : | 34.6 mg/ml ; 0.279 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.45 |
Solubility : | 4.39 mg/ml ; 0.0354 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
72% | Stage #1: for 16 h; Heating / reflux Stage #2: With sodium carbonate In ethanol; water |
Concentrated sulfuric acid (0.95 ml, 17.2 mmol, 0.5 equiv) is added to a solution of 6- aminonicotinic acid (5.0 g, 34.4 mmol) in ethanol (50 ml). After heating to reflux for 16 hours, the reaction mixture is carefully poured into a concentrated aqueous Na2CO3 solution. The aqueous phase is extracted three times with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue is dissolved in anhydrous THF (25 ml). At -60 0C, lithium aluminium hydride (2.68 g, 68.6 mmol, 3.0 equiv) is carefully added. The mixture is warmed to 0 0C, and then refluxed for 1 hour. After cooling, water (1.5 ml) and 5 N aqueous NaOH solution (1.5 ml) are added. The precipitate is filtered off, and the filtrate is concentrated in vacuo. The residue is purified via flash chromatography (EtOAc / MeOH 95 : 5) to afford the title compound (2.15 g, 72percent). 1H NMR (400 MHz, d6-DMSO): δ = 7.82 (d, J = 1.7 Hz, 1H), 7.32 (dd, J = 8.3 / 2.5 Hz, 1 H), 6.40 (dd, J = 9.3 / 1.0 Hz, 1 H), 5.77 (br s, 2H), 4.88 (t, J = 5.5 Hz, 1 H), 4.27 (d, J = 5.5 Hz, 2H). MS (ES+): 125 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran Stage #2: With methanol In tetrahydrofuran at 0℃; |
Compound 15 (1.0 equiv., 3.94 mmol, 0.600 g) was added portion wise to a suspension OfLiAlH4 (3.00 equiv., 11.83 mmol, 0.449 g) in dry THF (17 ml) at 00C. The reaction mixture was stirred at room temperature overnight. Excess LiAlH4 was destroyed by addition of methanol (while cooling on ice), the reaction mixture was filtered over Celite and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography (dichloromethane / methanol 75:25) to give 6-amino-3-pyridinemethanol (16) (0.330 g, yield = 67percent) as a white solid. 1H NMR (δ, CD3OD): 4.43 (2H, s), 6.58 (IH, d, J = 8.5 Hz), 7.48 (IH, dd, J = 8.5, ~ 2 Hz) 7.86 (IH, d, J ~ 2 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With hydrazine In methanol for 2 h; Heating / reflux | To a solution of acetic acid 6- (1, 3- dioxo-1, 3-dihydroisoindol-2-yl) pyridin-3-ylmethyl ester (0.200g, 0. 675mmol) was added methanol (lOmL). Hydrazine (0.065g, 2. 03mmol) was added and the mixture was heated to reflux for 2 hrs. A white precipitate formed after 30 min. The reaction was cooled to room temperature and filtered. The filtrate was concentrated and the residue was chromatographed on silica gel (Biotage 15,15percent 7N methanol ammonium/dichloromethane) to give 0.025g (30percent) of the title compound as clear oil. LCMS (APCI+) RT=0. 31 min. m/z 125 (M+H) +. |
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