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CAS No. : | 217448-86-7 | MDL No. : | MFCD16659092 |
Formula : | C11H9F2N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XVEURJOWGBWEPY-UHFFFAOYSA-N |
M.W : | 253.20 | Pubchem ID : | 22716778 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 56.97 |
TPSA : | 57.01 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.66 cm/s |
Log Po/w (iLOGP) : | 2.3 |
Log Po/w (XLOGP3) : | 1.67 |
Log Po/w (WLOGP) : | 2.23 |
Log Po/w (MLOGP) : | 2.12 |
Log Po/w (SILICOS-IT) : | 2.01 |
Consensus Log Po/w : | 2.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.65 |
Solubility : | 0.567 mg/ml ; 0.00224 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.48 |
Solubility : | 0.836 mg/ml ; 0.0033 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.6 |
Solubility : | 0.0637 mg/ml ; 0.000252 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
94% | With ascorbic acid In ethanol; water at 25℃; | Example 7Synthesis of Compound (II)Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate; 2,6-Difluorobenzyl azide (3.0 g, 17.7 mmoles) is suspended in ethanol (30 ml), then methyl propiolate (IV) (1.6 g, 19.6 mmoles), ascorbic acid (317 mg, 1.8 mmoles) and CuSO4 pentahydrate (50 mg, 0.18 mmole) are added. The reaction mixture is kept at 25° C. under stirring overnight. The mixture is concentrated, taken up with ethyl acetate and washed with an ammonia diluted solution. The organic phase is dried, filtered, concentrated under reduced pressure. A crystalline white solid is obtained in 94percent yield.1H NMR (400 MHz, DMSO-d6), δ ppm: 8.86 (s, 1H), 7.52 (m, 1H), 7.27-7.12 (m, 2H), 5.74 (s, 2H), 3.83 (s, 3H). |
94% | With ascorbic acid In ethanol at 25℃; | Example 7; Synthesis of compound (II): Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 2,6-Difluorobenzyl azide (3.0 g, 17.7 mmoles) is suspended in ethanol (30 ml), then methyl propiolate (IV) (1.6 g, 19.6 mmoles), ascorbic acid (317 mg, 1.8 mmoles) and CuSO4 pentahydrate (50 mg, 0.18 mmole) are added. The reaction mixture is kept at 25°C under stirring overnight. The mixture is concentrated, taken up with ethyl acetate and washed with an ammonia diluted solution. The organic phase is dried, filtered, concentrated under reduced pressure. A crystalline white solid is obtained in 94percent yield. 1H NMR (400 MHz, DMSO-d6), δ ppm: 8.86 (s, 1 H), 7.52 (m, 1H), 7.27-7.12 (m, 2H), 5.74 (s, 2H), 3.83 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: at 10 - 80℃; Stage #2: at 10 - 65℃; for 7 h; |
Example 3 Preparation of methyl-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate [(V), R is methyl]. Mixture of 120 g (0.502 mol) 1-(2, 6-difluorobenzyl)-1H-1, 2, 3-triazole-4-carboxylic acid (IV) and 1000 ml of methanol was stirred at ambient temperature. 25.10 gm sulphuric acid was added slowly followed by addition of 200 ml methanol. The reaction mixture was heated to 60-65° C. for 6 hours. Cooled to 10° C. for 1 hour. Solid was filtered, washed with methanol and dried under reduced pressure. Yield 111.15 g (87percent); HPLC purity: 99.92percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | at 60 - 65℃; for 6 h; | Mixture of 120 g (0.502 mol) l-(2, 6-difluorobenzyl)-lH-l, 2, 3-triazole-4-carboxylic acid (IV) and 1000 ml of methanol was stirred at ambient temperature. 25.10 gm sulphuric acid was added slowly followed by addition of 200 ml methanol. The reaction mixture was heated to 60-65°C for 6 hours. Cooled to 10°C for 1 hour. Solid was filtered, washed with methanol and dried under reduced pressure. Yield 111.15 g (87percent); HPLC purity: 99.92percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.3 g | With triethylamine In isopropyl alcohol at 75 - 80℃; for 25 h; | Example 5: Preparation of methyl l-(2, 6-difmorobenzyl)-lH-l,2,3-triazole- 4-carboxylate 2,6-difluorobenzyl azide (20 g), 2,3-dibromo methyl propionate (43.63 g), tri ethyl amine (19.36 g) and isopropyl alcohol (200 ml) were charged in a reaction vessel. The reaction mixture was heated to 75-80°C for 25 hours. The progress of the reaction was monitored by TLC. After completion of the reaction, isopropyl alcohol was evaporated in vacuum to give brown solid to which water was added and extracted using dichloromethane (150 ml). The organic layer was washed with brine, dried on sodium sulphate and evaporated in vacuum below 40°C to give brown solid. This solid was slurried in n-heptane, filtered and dried at 60-65°C to give methyl l-(2, 6-difluorobenzyl)-lH-l,2,3- triazole- 4-carboxylate (19.3g) as light brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
120 g | at 75 - 80℃; for 24 h; | Example-3 Preparation of methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate A mixture of 2-(azidomethyl)-1,3-difluorobenzene in t-butanol prepared as per example 2, methyl 2-bromoacrylate (120 gms) and water (200 ml) were heated to 75-80° C. The contents was stirred at 75-80° C. for 24 hours. After the completion of reaction, the reaction mixture was cooled to room temperature. The solid obtained was filtered and then crude mass was added to cyclohexane (240 ml) and the mixture was stirred at room temperature for 2 hours. The solid was filtered and washed with cyclohexane (50 ml). The product was dried for 2 hours to give methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate. Yield: 120gms |
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