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CAS No. : | 864076-05-1 | MDL No. : | MFCD13189816 |
Formula : | C6H7BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ROEZBNMDDJUDSC-UHFFFAOYSA-N |
M.W : | 219.04 | Pubchem ID : | 53302209 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.47 |
TPSA : | 44.12 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) : | -6.77 cm/s |
Log Po/w (iLOGP) : | 2.12 |
Log Po/w (XLOGP3) : | 1.22 |
Log Po/w (WLOGP) : | 0.97 |
Log Po/w (MLOGP) : | 0.36 |
Log Po/w (SILICOS-IT) : | 0.87 |
Consensus Log Po/w : | 1.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.17 |
Solubility : | 1.48 mg/ml ; 0.00675 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.74 |
Solubility : | 3.95 mg/ml ; 0.018 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.73 |
Solubility : | 4.05 mg/ml ; 0.0185 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.22 |
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 |
---|---|---|
81% | Stage #1: at 20℃; Reflux Stage #2: at 20℃; for 3 h; |
A suspension of 1-(4-bromo-l-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanone (0.266 g, 868 μιηο, Eq: 1) in methanol (1.11 g, 1.41 ml, 34.7 mmol, Eq: 40) was heated to reflux for 3 hours then at room temperature overnight. To the reaction mixture, sodium methoxide (15.6 mg, 16.1 μ, 86.8 μιηο, Eq: 0.1) was added and stirring was continued at room temperature for 3 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the desired product as a light brown solid (155 mg, 81 percent). MS (m/z) = 219.1, 221.1 [(M+H)+]. |
68% | at 25℃; for 0.333333 h; | To the solution of 1.18 g of 1-(-4-bromo-1-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanone in 10 mL of methanol was added 42 mg of sodium methoxide and the resulting mixture was stirred at 25° C. for 20 min. TLC showed completion of the reaction. The solution was evaporated, redissolved in 30 mL of DCM, washed with water (15 mL.x.2) and brine (15 mL). The solution was dried over anhydrous sodium sulfate and filtered. The residue was purified by silica gel column (DCM/MeOH=60/1) to give 4-bromo-1-methyl-1H-imidazole-2-carboxylic acid methyl ester (0.575 g, yield 68percent). 1H NMR (300 MHz, CDCl3) δ 7.02 (s, 1H), 4.00 (s, 3H). 3.93 (s, 3H). LC-MS calcd for C6H7BrN2O2 (m/e) 217.97, obsd 219 and 221 [M+1]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | at 20℃; for 0.5 h; | A solution of SI-2 (1.91 g, 6.24 mmol) and DMAP (305 mg, 2.50 mmol) in MeOH (31 mL) was stirred for 30min at room temperature. The reaction mixture was evaporated and the obtained residue was purified by silica gel column chromatography (SiO2, EtOAc) to give the desired product 6a (1.32 g, 96percent yield) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15.6% | Stage #1: With N-Bromosuccinimide In tetrahydrofuran at -10 - 20℃; for 14 h; Stage #2: at 75℃; for 1 h; |
Step 2To a stirred solution of 2,2,2-trichloro-l-(l-methyl-lH-imidazol-2-yl)ethanone (12.42 g, 54.6 mmol) in THF (40 mL) at -10 0C was added n-bromosuccinimide (6.95 ml, 81.9 mmol). The reaction mixturewas kept at -10 0C for 2 h, warmed to RT with stirring for 12 h and concentrated. The residue was purified with ISCO using straight DCM. The solid obtained was dissolved in MeOH (40 mL), 60percent NaH (80 mg) was added and the reaction mixture heated to 75 0C for 1 h. The reaction mixturewas concentrated and the residue purified with ISCO using 0-10percent EtOAc in DCM to give methyl 4-bromo-l-methyl-lH-imidazole-2- carboxylate (1.86 g, 15.6percent yield). |
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