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CAS No. : | 1422205-93-3 | MDL No. : | MFCD28523171 |
Formula : | C9H9N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UXYQMISKWTUVMQ-UHFFFAOYSA-N |
M.W : | 191.19 | Pubchem ID : | 84663096 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 51.78 |
TPSA : | 81.0 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) : | -7.0 cm/s |
Log Po/w (iLOGP) : | 0.79 |
Log Po/w (XLOGP3) : | 0.66 |
Log Po/w (WLOGP) : | 0.94 |
Log Po/w (MLOGP) : | 0.34 |
Log Po/w (SILICOS-IT) : | 1.11 |
Consensus Log Po/w : | 0.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.78 |
Solubility : | 3.14 mg/ml ; 0.0164 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.94 |
Solubility : | 2.21 mg/ml ; 0.0116 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.63 |
Solubility : | 0.447 mg/ml ; 0.00234 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.75 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
269 mg | With 5%-palladium/activated carbon; hydrogen; In methanol; under 760.051 Torr; | [Step 3] Methyl 6-amino-1H-benzimidazole-4-carboxylate Methyl 6-nitro-1H-benzimidazole-4-carboxylate (304 mg) was suspended in MeOH (10 mL), the suspension was added with 5% palladium on carbon (30 mg), and stirred under hydrogen (1 atm) atmosphere. The catalyst was filtered off on celite and washed with MeOH, and the mother liquor was concentrated in vacuo to obtain the titled compound (269 mg) as pale yellow powder. MS(ESI+) m/z 192(M+H)+ |
With 5%-palladium/activated carbon; hydrogen; In methanol; under 760.051 Torr; | Methyl 6-nitro-1H-benzimidazole-4-carboxylate (304 mg) was suspended in MeOH (10 mL), the suspensionwas added with 5% palladium on carbon (30 mg), and stirred under hydrogen (1 atm) atmosphere. The catalyst wasfiltered off on celite and washed with MeOH, and the mother liquor was concentrated in vacuo to obtain the titledcompound (269 mg) as pale yellow powder.MS(ESI+) m/z 192(M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
309 mg | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 3.0h;Cooling with ice; | [Step 4] methyl 6-([2-(Trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimida zole-4-carboxylate To a solution of <strong>[1422205-93-3]methyl 6-amino-1H-benzimidazole-4-carboxylate</strong> (266 mg) in dehydrated THF (12 mL), N,N-diisopropylethylamine (284 muL) was added, and the solution was stirred under ice-cooling. To this solution, 2-(trifluoromethyl)benzoyl chloride (284 muL) in dehydrated THF (5 mL) was added slowly dropwise, and stirred at the same temperature for 3 hours. After ice water was added, THF was removed under reduced pressure, and aqueous saturated sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on NH silica gel column chromatography (ethyl acetate -> ethyl acetate/MeOH) to obtain the titled compound (309 mg) as pale yellow powder. |
309 mg | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 3.0h;Cooling with ice; | To a solution of <strong>[1422205-93-3]methyl 6-amino-1H-benzimidazole-4-carboxylate</strong> (266 mg) in dehydrated THF (12 mL), N,Ndiisopropylethylamine(284 mL) was added, and the solution was stirred under ice-cooling. To this solution, 2- (trifluoromethyl)benzoyl chloride (284 mL) in dehydrated THF (5 mL) was added slowly dropwise, and stirred at the sametemperature for 3 hours. After ice water was added, THF was removed under reduced pressure, and aqueous saturatedsodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed withbrine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residuewas purified on NH silica gel column chromatography (ethyl acetate -> ethyl acetate/MeOH) to obtain the titled compound(309 mg) as pale yellow powder. |
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