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CAS No. : | 20485-43-2 | MDL No. : | MFCD01863421 |
Formula : | C5H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WLDPWZQYAVZTTP-UHFFFAOYSA-N |
M.W : | 126.11 | Pubchem ID : | 557678 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 30.45 |
TPSA : | 55.12 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) : | -7.16 cm/s |
Log Po/w (iLOGP) : | 1.05 |
Log Po/w (XLOGP3) : | -0.13 |
Log Po/w (WLOGP) : | 0.12 |
Log Po/w (MLOGP) : | -0.8 |
Log Po/w (SILICOS-IT) : | -0.26 |
Consensus Log Po/w : | 0.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.89 |
Solubility : | 16.4 mg/ml ; 0.13 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.57 |
Solubility : | 33.6 mg/ml ; 0.267 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.13 |
Solubility : | 93.7 mg/ml ; 0.743 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.31 |
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% | With dihydrogen peroxide In water at 20℃; for 72 h; | First, 1-methylimidazole-2-carboxaldehyde was prepared according to the literature procedure[23]. The synthesis procedure then followed that of Im2COOH (1b) above and the yield was also quantitative after the removal of water under high vacuum (no washing with diethylether/water was necessary). Note: heating causes decarboxylation. Yield: 100percent. Mp=99–101°C. δH (400MHz, D2O): 7.42, 7.39 (2H, s, Im-H) and 4.08ppm (3H, s, NCH3); δC (400MHz, D2O): 158.67, 139.68, 125.83, 118.46, 36.73ppm. IR ν (KBr): 3347(m) 3119(m), 2663(w), 1641(s), 1683(m), 1507(s), 1449(m), 1388(s), 1338(s), 1285(s), 1173(m), 1123(s), 961(m) 910(m), 776(s), 685(s) cm−1. Anal. Calc. for C5H8N2O3 (144.12); C, 41.67; H, 5.59; N, 19.44percent. Found: C, 41.28; H, 5.23; N, 19.12percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: for 1 h; Heating / reflux Stage #2: With hydrogenchloride In water at 5 - 50℃; |
Dry acetonitrile (600 ML) was added to N-methylimidazole (150 g, 1.8 mol), followed by triethylamine (503 ML, 3.6 mol) in one portion, and the mixture cooled TO-30 °C. Neat ethyl chloroformate (350 mL, 3.6 mol) was added slowly over 15 min. The turbid mixture was then warmed to room temperature and maintained overnight. The solid triethyl ammonium chloride was filtered off, washed with EtOAc, and the filtrate concentrated in vacuo. Dichloromethane (500 ML) was added and the solution was extracted with water (300 mL), the organic phase dried with magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (SIO2, EtOAc) and recrystallization from ether/heptane (2: 1) to provide 188 g (66percent) of N-METHYLIMIDAZOLE-2-CARBOXY ethyl ester. This N-methylimidazole-2-carboxy ethyl ester (120 g, 0.77 mol) was treated with a solution of sodium hydroxide (37 g, 0.9 mol) in water (60 mL), and the mixture heated at reflux for 1 h. The mixture cooled to 50 °C, acidified to pH 2 with concentrated HC1, cooled further to 5 °C and the precipitate filtered. The solid was washed with ether, diluted into water (70 mL), heated gently under 60 °C, and upon cooling the product crystallizes to give 75 g (77percent) of N-METHYLIMIDAZOLE-2-CARBOXYLIC acid, which was converted into the corresponding aldehyde as described for Intermediate 23. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: With sodium hydroxide In water for 1 h; Reflux Stage #2: With hydrogenchloride In water |
A solution of the methylimidazole (3.2 mL, 40.0 mmol) in 30 mL de CH3CN:Et3N (2:1) was cooled to –30 C and quickly added to a previously prepared solution of ethyl chloroformiate (7 mL, 66.0 mmol) in 10 mL of CH3CN. The mixture was stirred for 15h at rt. The solvents were removed under reduced pressure; the crude was re-dissolved in water (20 mL) and extracted with chloroform (3 × 20 mL). The organic fractions were dried and concentrated, and the resulting residue was purified by flash cromatography (aluminum oxide, 90percent MeOH) to give 3.72 g of a crude ester residue which was directly used for the next step. A solution of this residue (1.5 g, 9.74 mmol) in 15 mL of aqueous NaOH (1 M) was refluxed for 1 h. The resulting mixture was acidified to pH 2.0 using HCl 10percent (aprox.15 mL) and lyophilized. The crude was dissolved in MeOH and concentrated underreduced pressure to give 12 as a slighlty pink solid (1.2 g, 98percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine In acetonitrile | Ethy 1-methylimidazole-2-carboxylate N-methylnimdazole (320 g, 3.9 mol) was combined with 2 L acetonitrile and 1 L triethylamine in a 12 L flask equipped with a mechanical stirrer and the solution cooled to -20° C. Ethyl chloroformate (1000 g, 9.2 mol) was added with stirring, keeping the temperature between -20° C. and -25° C. The reaction was allowed to slowly warm to room temperature and stir for 36 h. Precipitated triethylamine hydrochloride was removed by filtration and the solution concentrated in vacuo at 65° C. The resulting oil was purified by distillation under reduced pressure (2 torr, 102° C.) to provide a white solid (360 g, 82percent yield). |
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