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CAS No. : | 34604-60-9 | MDL No. : | MFCD11978170 |
Formula : | C5H4N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CGQFCIHUUCMACC-UHFFFAOYSA-N |
M.W : | 140.10 | Pubchem ID : | 161825 |
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 : | 2.0 |
Molar Refractivity : | 31.82 |
TPSA : | 83.05 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) : | -7.85 cm/s |
Log Po/w (iLOGP) : | 0.19 |
Log Po/w (XLOGP3) : | -0.98 |
Log Po/w (WLOGP) : | -0.53 |
Log Po/w (MLOGP) : | -1.36 |
Log Po/w (SILICOS-IT) : | 0.47 |
Consensus Log Po/w : | -0.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.47 |
Solubility : | 47.6 mg/ml ; 0.339 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.28 |
Solubility : | 73.8 mg/ml ; 0.527 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.91 |
Solubility : | 17.4 mg/ml ; 0.124 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
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 |
---|---|---|
65% | Stage #1: at -20℃; for 0.5 h; Stage #2: for 2 h; Reflux |
Preparation 405-Hvdroxy-pyrazine-2-carboxylic acid methyl esterThionyl chloride (152ml_, 2.08mol) was added dropwise at -20 °C to methanol (5L). After the addition was completed, the mixture was stirred at this temperature for 30 minutes. Then 5- hydroxy-pyrazine-2-carboxylic acid (100g, 714mmol) was added, and the mixture was heated at reflux for 2 hours. The reaction mixture was concentrated in vacuo, and the residue was recrystallised from methanol (400ml_) to give 71 g (464mmol) of the title compound in 65percent yield. |
61% | With hydrogenchloride In 1,4-dioxane; water at 60 - 80℃; for 4 h; | (62a) Methyl 5-hydroxypyrazine-2-carboxylate Commercially available 5-hydroxypyrazine-2-carboxylic acid (1.00 g, 7.14 mmol) was dissolved in methanol (5 mL), and a 4N hydrochloric acid/dioxane solution (25 mL) was added, followed by stirring at 60°C for 1.5 hours and heating to reflux at 80°C for 2.5 hours. The reaction solution was brought back to room temperature, the solvent was distilled off under reduced pressure, and ethyl acetate (20 mL) was added to the resulting residue to allow it to be suspended. The resulting precipitate was filtered off, and washed with ethyl acetate, followed by vacuum drying, to afford the desired compound (673 mg, yield 61percent) as an orange-brown solid. 1H-NMR (CD3OD, 400 MHz): δ 3.31 (1H, s), 3.85 (3H, s), 8.00 (1H, d, J=1.2 Hz), 8.13 (1H, d, J=1.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 16 h; | Step 1: Preparation of 5-chloropyrazine-2-carboxylic acid [0170] To a solution 5-hydroxypyrazine-2-carboxylic acid (10 g, 71.42 mmol) in thionyl chloride (100 mL) was added N, N- dimethyl formamide (1 mL) and the reaction mixture was stirred at 80 °C for 16 h. Thionyl chloride was distilled off, the residue was diluted with ice water and extracted ethyl acetate (600 mL x 3). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude was triturated with diethyl ether to afford the title compound 5-chloropyrazine-2-carboxylic acid (10.53 g, 93percent yield) as a brown solid. Calculated M+H: 158.99; Found M+H: 159.0. |
75% | for 16 h; Reflux | Intermediate 44; 5-Chloropyrazine-2-carboxylic acid; 5-Hydroxypyrazine-2-carboxylic acid (1.0 g, 0.007 mol) was taken in thionyl chloride (10 mL), to this solution dimethylformamide (0.1 mL) was added which was heated to reflux for 16 h. After this period, excess thionyl chloride was distilled off to get crude compound, which was added to ice (20 g) and extracted with ethyl acetate (2 x 70 mL). The organic layers were combined and dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain brown solid which was triturated with diethyl ether (30 mL) to afford 600 mg (75percent) of 5-chloropyrazine-2-carboxylic acid.1H NMR (400 MHz, DMSO-d): δ 8.94 (s, IH), 9.04 (s, IH), 13.92 (s, IH). Mass (APCI): m/z 157.0 (M-H). |
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