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CAS No. : | 26663-77-4 | MDL No. : | MFCD03407310 |
Formula : | C9H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WJHHIVYNOVTVGY-UHFFFAOYSA-N |
M.W : | 176.17 | Pubchem ID : | 2779733 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.37 |
TPSA : | 54.98 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.2 cm/s |
Log Po/w (iLOGP) : | 1.39 |
Log Po/w (XLOGP3) : | 1.66 |
Log Po/w (WLOGP) : | 1.35 |
Log Po/w (MLOGP) : | 0.9 |
Log Po/w (SILICOS-IT) : | 1.84 |
Consensus Log Po/w : | 1.43 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.36 |
Solubility : | 0.772 mg/ml ; 0.00438 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.43 |
Solubility : | 0.657 mg/ml ; 0.00373 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.98 |
Solubility : | 0.183 mg/ml ; 0.00104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.45 |
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 |
---|---|---|
67% | With methanol; sodium hydroxide In tetrahydrofuran at 70℃; | Step 1: A mixture of compound 1 (520 mg, 3 mol) and 2M NaOH (5 ml) in MeOH (10 ml) and THF (10 ml) was stirred 70°C for overnight. TLC was used to monitor the reaction. The mixture was then concentrated to a residue, added water (30mL) and used citric acid to adjust PHto 5-6. Extracted with EA, the organic layer was separated, washed, dried, filtered and concentrated to get compound 4 as yellow solid (320 mg, 67percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | for 12 h; Heating / reflux | Example 109; (2Z50-5- (l-benzimidazol-5-vlmethvlidene)-2- [ (2. 6-dichlorophenvl) imino]-1. 3-t hiazolidin-4-one; (a) methyl lH-benzimidazole-5-carboxylate; Thionyl Chloride (0.135 mL, 1. 85 mmol) was added dropwise to a solution of lH-benzimidazole-5-carboxylic acid (0.300 g, 1.85 mmol) in methanol (50.0 mL). The solution was refluxed for 12 h and then cooled to room temperature. The mixture was slurried into sat. aq. sodium hydrogen carbonate, separated into layers and extracted using ethyl acetate (3 x 15 mL). The combined organic layers are dried over magnesium sulfate, filtrated and concentrated to give a purple solid as the desired product in 90 percent yield. The crude was used without further purification. [MS (ES+) m/e 177 [M+H] +]. |
90% | at 0℃; for 18 h; Reflux | Example 1 N2-((lH-Benzo[d]imidazol-5-yl)methyl)-N'-(5-cyclopropyl-lH-pyrazol-3-yl)pyrimidine-2,4- diamine (I- 13) step 1 : Thionyl chloride (10 mL) was added dropwise to a solution of lH-benzo[d]imidazole-5-carboxylic acid (4.8 g, 30 mmol) in MeOH (150 mL) cooled to 0 °C. The reaction mixture was heated at reflux for 18 h, and then solvent (about 2/3) was concentrated under reduced pressure. After cooling, a yellow solid was precipitated from the solution and was filtered to afford 4 g (90percent) of methyl lH-benzo[d]imidazole- 5-carboxylate (20): MS (ESI) m/z = 111 [M+l]+. |
90% | for 12 h; Heating / reflux | Thionyl Chloride (0.135 ml_, 1.85 mmol) was added dropwise to a solution of 1 /-/-benzimidazole-5-carboxylic acid (0.300 g, 1.85 mmol) in methanol (50.0 ml_). The solution was refluxed for 12 h and then cooled to room temperature. The mixture was slurried into sat. aq. sodium hydrogen carbonate, separated into layers and extracted using ethyl acetate (3 x 15 ml_). The combined organic layers are dried over magnesium sulfate, filtrated and concentrated to give a purple solid as the desired product in 90 percent yield. The crude was used without further purification. [MS(ES+) m/e 177 [M+H]+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sulfuric acid; sodium hydrogencarbonate In methanol | 8.1. PREPARATION OF 5-BENZIMIDAZOLE-CARBOXYLIC ACID, METHYL ESTER A 500 ml round bottom flask equipped with a heating mantle, reflux condenser, and a DrieriteR filled drying tube was charged with 16.22 g (0.10 mol) of 5-benzimidazolecarboxylic acid (Aldrich), 400 ml of anhydrous methanol and then (Caution)) 20 ml of concentrated sulfuric acid (Fisher). The reaction mixture was heated to reflux for 18 h and then cooled to ambient temperature. Approximately 75percent of the solvents were removed under vacuum and then the remaining liquid residue was slowly poured into 500 ml of saturated sodium bicarbonate solution. The resultant two phase system was then extracted with three 250 ml portions of ethyl acetate. The organic layers were combined and washed with three 250 ml portions of 5percent sodium bicarbonate solution followed by one 250 ml portion of brine. The ethyl acetate layer was dried over MgSO4, filtered and the solvents were then removed under reduced pressure to give 15.68 g (0,089 mol, 89percent yield) of 5-benzimidazolecarboxylic acid, methyl ester, as a tan solid. 1 H NMR (CDCl3) δ7.3-7.9 (m, 3H), 3.70 (s, 3H). |
89% | With sulfuric acid; sodium hydrogencarbonate In methanol | 8.1. PREPARATION OF 5-BENZIMIDAZOLECARBOXYLIC ACID, METHYL ESTER, 10 A 500 ml round bottom flask equipped with a heating mantle, reflux condenser, and a Drierite.(R). filled drying tube was charged with 16.22 g (0.10 mol) of 5-benzimidazolecarboxylic acid (Aldrich), 400 ml of anhydrous methanol and then (Caution)) 20 ml of concentrated sulfuric acid (Fisher). The reaction mixture was heated to reflux for 18 h and then cooled to ambient temperature. Approximately 75percent of the solvents were removed under vacuum and then the remaining liquid residue was slowly poured into 500 ml of saturated sodium bicarbonate solution. The resultant two phase system was then extracted with three 250 ml portions of ethyl acetate. The organic layers were combined and washed with three 250 ml portions of 5percent sodium bicarbonate solution followed by one 250 ml portion of brine. The ethyl acetate layer was dried over MgSO4, filtered and the solvents were then removed under reduced pressure to give 15.68 g (0.089 mol, 89percent yield) of 5-benzimidazolecarboxylic acid, methyl ester, 10, as a tan solid. 1 H NMR (CDCl3, TMS): δ7.3-7.9 (m, 3H), 3.70 (s, 3H). |
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