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Structure of 165806-95-1
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 165806-95-1 |
Formula : | C15H12FNO2S |
M.W : | 289.33 |
SMILES Code : | FC1=CC=C(C=C1)C([N+]#[C-])S(=O)(C2=CC=C(C)C=C2)=O |
MDL No. : | MFCD03787932 |
InChI Key : | UXCQPEDHCCJBNL-UHFFFAOYSA-N |
Pubchem ID : | 10827289 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301-H315-H319-H335 |
Precautionary Statements: | P261-P301+P310-P305+P351+P338 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
Example 50: Synthesis of {4-[5-(4-Fluoro-phenyl)-3-methyl-3H-imidazol-4-yl]-pyridin-2- yl}-ureaStep 1: Synthesis of 2-Bromo-4-[5-(4-fluoro-phenyl)-3-methyl-3H-imidazol-4-yl]-pyridine2-Bromo-pyridine-4-carbaldehyde (479 mg, 2.58 mmol) and 2.0 M methylamine THF solution (1.73 mL, 3.46 mmol) are mixed in THF (6.0 mL) and the reaction mixture is stirred for 4 hrs at room temperature. Then piperazine (224 mg, 2.58 mmol) and [l-(4-fluorophenyl)-l- tosyljmethylisocyanide (500 mg, 1.73 mmol) are added. The reaction mixture is stirred for another 16 hrs before water (35 mL) is added. The resulting mixture is extracted with EtOAc (3 x 35 mL) and the organic layers are combined, washed with saturated NaHCC>3 aqueous solution (20 ml) and water (25 mL), dried and concentrated to give the crude product. Purification by silica flash column chromatography using EtOAc in heptane (gradient from 20percent to 90percent) affords 460 mg of desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperazine; ammonium hydroxide; In tetrahydrofuran; water; at 20℃; for 16h; | Example 54: Synthesis of {4-[4-(4-Fluoro-phenyl)-oxazol-5-yl]-pyridin-2-yl}-ureaStep 1: Synthesis of 2-Bromo-4-[4-(4-fluoro-phenyl)-oxazol-5-yl]-pyridine2-Bromo-pyridine-4-carbaldehyde (958 mg, 5.15 mmol), 28percent aqueous ammonium hydroxide solution (2.01 mL, 15.5 mmol), piperazine (448 mg, 5.15 mmol) and [l-(4-fluorophenyl)-l- tosyljmethylisocyanide (1.0 g, 3.5 mmol) are mixed in THF (15 mL). The reaction mixture is stirred for 16 hrs at room temperature. Then water (35 mL) is added and the mixture is extracted with EtOAc (3 x 25 mL). The organic layers are combined, washed with saturated NaHCC>3 aqueous solution (20 mL) and water (25 mL), dried and concentrated to give the crude product. Purification by silica flash column chromatography using EtOAc in heptane (gradient from 10percent to 80percent) affords 748 mg of desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used |
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