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CAS No. : | 107818-55-3 | MDL No. : | MFCD12031265 |
Formula : | C6H6BrNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RZYLOBBUEWSONL-UHFFFAOYSA-N |
M.W : | 236.09 | Pubchem ID : | 20158931 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.7 |
TPSA : | 80.56 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.84 cm/s |
Log Po/w (iLOGP) : | 1.95 |
Log Po/w (XLOGP3) : | 2.68 |
Log Po/w (WLOGP) : | 1.89 |
Log Po/w (MLOGP) : | 1.08 |
Log Po/w (SILICOS-IT) : | 2.36 |
Consensus Log Po/w : | 1.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.15 mg/ml ; 0.000636 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.02 |
Solubility : | 0.0223 mg/ml ; 0.0000946 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.24 |
Solubility : | 1.35 mg/ml ; 0.00571 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.49 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 |
---|---|---|
57% | With phenyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane at 20℃; for 24 h; | After dissolving the compound of formula 1-1-1 (15.72 g, 0.1 mol, 1.0 equiv.) In dried DCM (150 mL) and MeOH (150 mL), phenyltrimethylammonium tribromide (112.78 g, 0.3 Mol, 3 equiv.) And calcium carbonate (40.04 g, 0.4 mol, 4 equiv.) Were added dropwise and the mixture was stirred at room temperature for 24 hours. When the reaction was complete, it was filtered and washed with EtOAc. The filtrate was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure, and subjected to flash column chromatography to obtain the compound of Formula 1-1-2 (yield: 57percent) |
57% | With phenyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane at 20℃; | Example 1N-(3-aminopropyl)-N- [ 1 -(3 -benzyl-6-bromo-4-oxo-3,4-dihydrothieno [3,2-dlpyrimidin-2-vl)-2-(dimetfavlaminoV2-oxoethyl]-4-methylbenzamide (Compound 5 in Table 1)Step 1. Methyl 3-amino-5-bromothiophene-2-carboxylate.Br3~ ^ "| ]CO2Me [\\^J Br-_xS\\/CO2MeCaCO3 \\ILJNH2 MeOH / CH2CI2 2rtMethyl-3-amino-2-thiophene carboxylate (1 eq. 25 g) was dissolved in 250 ml methylene chloride and 250 ml of methanol. Phenyl trimethylammonium tribromide (3 eq. 180 g) was added followed by calcium carbonate (4 eq. 63.75 g) and the reaction was left stirring at room temperature overnight. The calcium carbonate was filtered off and the filtrate concentrated down and water (750 ml) was added followed by ethyl acetate (1 L). The ethyl acetate layer was washed with more water, sodium thiosulfate, saturated sodium bicarbonate and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography to yield 21.46 g (57percent) of methyl 3-amino-5-bromothiophene-2-carboxylate as a light brown oil, MH+ = 238.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With water; potassium carbonate In methanol at 20℃; for 2 h; | A mixture of methyl 5-bromo-3- [ (trifluoroacetyl) amino] thiophene-2-carboxylate (5.30 g, 16.0 mmol), potassium carbonate (10.2 g, 70.4 mmol), MeOH (100 mL) and water (25 mL) was stirred at room temperature for 2 h. After removal of the solvent at reduced pressure, the residue was extracted with EtOAc, and the extract was washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, hexane to 10:90 hexane/EtOAc) to give the title compound (3.32 g, 88percent) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 3.70 (3H, s), 6.68 (2H, br s) , 6.75 (IH, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: With bromine In tetrahydrofuran; hexane at -78 - 20℃; for 2.5 h; Stage #3: With water; potassium carbonate In methanol at 20℃; for 1.5 h; |
To stirred tetrahydrofuran (100 inL) at -78°C were added dropwise diisopropylamine (9.00 mL, 63.9 mmol) and n-butyl lithium (37.1 mL, 59.4 mmol, 1.6 M solution in n-hexane) successively. The reaction mixture was allowed to warm to 00C and stirred for additional 10 min. The mixture was cooled to -78°C again and methyl 3- (2,2, 2- trifluoroacetamido) thiophene-2-carboxylate (4.56 g, 18.0 mmol) was added to the mixture. After 1 h, bromine (2.78 mL, 54.0 mmol) was added to the mixture, and stirring was continued at -78°C for 2 h and at room temperature for 30 min. The mixture was then poured into sat. aqueous sodium hydrogen carbonate (180 mL) . Extraction with ethyl acetate (150 mL) , washing with brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was purified by column chromatography (Combiflash, 12 g silica gel, hexanes to 90:10 hexanes/ethyl acetate) to afford a mixture of the title compound and methyl 3-aminothiophene-2-carboxylate (1.86 g) as a white solid. The ratio was about 2:1 estimated by 1H NMR analysis:1H NMR (300 MHz, DMSO-d6) δ 3.84 (3H, s) , 7.79 (IH, s) , 11.22 (IH, br s) .A mixture of methyl 5-bromo-3- (2, 2, 2- trifluoroacetamido) thiophene-2-carboxylate (1.86 g) , potassium carbonate (3.72 g, 26.9 mmol), methanol (40 mL) and water (10 mL) was stirred at room temperature for 1.5 h. The mixture was concentrated in vacuo and then ethyl acetate and water were added to the residue for extraction. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Combiflash, silica gel, hexanes to 90:10 hexanes/ethyl acetate) to afford the title compound (0.781 g, 18percent from methyl 3- (2, 2, 2-trifluoroacetamido) thiophene-2- carboxylate) as a white solid:1H NMR (300 MHz, DMSO-d6) δ 3.70 (3H, s), 6.69 (2H,br s) , 6.75 (IH, s). |
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