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CAS No. : | 27398-39-6 | MDL No. : | MFCD01318438 |
Formula : | C5H3ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PMRPVXLESNMKLG-UHFFFAOYSA-N |
M.W : | 158.54 | Pubchem ID : | 1501900 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 34.0 |
TPSA : | 63.08 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) : | -6.84 cm/s |
Log Po/w (iLOGP) : | 0.6 |
Log Po/w (XLOGP3) : | 0.6 |
Log Po/w (WLOGP) : | 0.83 |
Log Po/w (MLOGP) : | -0.61 |
Log Po/w (SILICOS-IT) : | 0.97 |
Consensus Log Po/w : | 0.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.58 |
Solubility : | 4.18 mg/ml ; 0.0264 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.5 |
Solubility : | 5.03 mg/ml ; 0.0317 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.63 |
Solubility : | 3.72 mg/ml ; 0.0234 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
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 |
---|---|---|
100 mg | With diazomethyl-trimethyl-silane In dichloromethane at 20℃; for 2 h; | To a solution of 3-.chioropyrazine-.2—carboxyiic acid (100 mg, 0.63 mmoi) in DCM/MeOFI (2 mL : ().2 mL) was added TMSCHN2 (0.47 mL, 0.95 mmoi) at RT and the resulting mixture stirred at RT for 2 h. Acetic acid (0.2 mL) was added and the mixture diluted with water (2 mL) and extracted with DCM (4 mL x 3). The combined organic layers werewashed with brine, dried over Na2 SO4, filtered and concentrated in vacuo to give the title compound (100 mg) as a colorless oil. LRMS mIz (M+H) 173.0 found, 173.0 required. Step 2: Methyl 3-.pyridin-.2-.yl)pyrazine—2--carboxyiate (M2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Stage #1: With triethylamine; methyl chloroformate In tetrahydrofuran for 0.5 h; Cooling with ice Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water for 1 h; Cooling with ice |
3-Chloropyrazine-2-carboxylic acid (2.97 g, 18.73 mmol, 1 eq.) was dissolved in tetrahydrofuran (75 mL). The solution was stirred in an ice bath and triethylamine (5.2 mL, 37.5 mmol, 2 eq.) was added followed by addition of methyl chloroformate (1.74 mL, 22.5 mmol, 1.2 eq.) dropwise. After 30 m, the reaction was filtered and the solid rinsed with more tetrahydrofuran (10 mL). The tetrahydyofuran solution was stirred in an ice bath and a suspension of sodium borohydride (1.4 g, 37.5 mmol, 2 eq.) in water (3 mL) was added. After 1 h, a saturated aqueous ammonium chloride solution (100 mL) was added to the reaction and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic phases were washed with a saturated aqueous sodium chloride solution (25 mL) and dried over sodium sulfate. After filtration and evaporation, the residue was purified by silica gel chromatography (5 - 70percent ethyl acetate/hexanes) to give (3-chloropyrazin-2-yl)methanol (0.84 g, 31percent) as a faintly colored oil. |
22% | Stage #1: With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; for 0.166667 h; Stage #2: With sodium tetrahydroborate In water at 0℃; for 1 h; |
102901 To a solution of 3-chloropyrazine-2-carboxylic acid (2.0 g, 12.70 mmol, 1.0 eq.) andTEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL,15.20 mmol, 1.2 eq.) atO °C. The mixture was stirred at 0°C for 10 mm and filtered. To thisfiltrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0 °C. The mixture was stirred at 0 °C for 1 h, quenched with NH4C1 (aq) solution, and extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2- yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) 8.58 (d,J 2.5 Hz,1H), 8.38 (d,J= 2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 0.166667 h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1 h; |
Step 1 To a solution of 3-chloropyrazine-2-carboxylic acid (2.0 g, 12.70 mmol, 1.0 eq.) and TEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL, 15.20 mmol, 1.2 eq.) at 0° C. The mixture was stirred at 0° C. for 10 min and filtered. To this filtrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, quenched with NH4Cl(aq) solution, and extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2-yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) δ 8.58 (d, J=2.5 Hz, 1H), 8.38 (d, J=2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1. |
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