Structure of 17115-51-4
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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. : | 17115-51-4 |
Formula : | C4H6O3S |
M.W : | 134.15 |
SMILES Code : | O=C(CC1)CS1(=O)=O |
MDL No. : | MFCD00154869 |
InChI Key : | UOEHJNULMZMQNM-UHFFFAOYSA-N |
Pubchem ID : | 5150067 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With manganese(II) oxide; In dichloromethane; at 20℃; for 16h; | Mn02 (35 equiv, 2.2 g) was added to the alcohol (1 equiv, 100 mg) in DCM (20 mL) and the reaction was stirred at room temperature for 16 h. The reaction mixture was filtered and concentrated in vacuo. The residue was used in the next step without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; | EXAMPLE 10C Tetrahydrothiophene-3-one-1,1-dioxide A mechanically stirred solution of the crude product from Example 10B in acetone (300 mL) was treated with Jones reagent (2.7M, 30 mL total) in portions over 2 hours until the brown color persisted, stirred for 1 hour, treated slowly with isopropyl alcohol (7.5 mL), stirred for 15 minutes, diluted with acetone (400 mL) and filtered through celite to remove the chromium salts. The filtrate was concentrated and purified by chromatography on silica gel (1:1 hexane:ethyl acetate) to provide 5.88 g of the title compound. 1H NMR (CDCl3) δ 3.08 (t, 2H), 3.58 (t, 2H), 3.70 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene; | EXAMPLE 1 1-tert-butyl-3-(4,5-dihydro-3-thienyl)urea S,S-Dioxide To a solution of 6.7 g 3-oxo-tetrahydrothiophene S,S-dioxide [(J. Chem. Soc. (C), 2171 (1967)] in 100 ml of benzene is added 5.6 g of tert-butyl urea and 100 mg p-toluene acid. The solution is heated at reflux under nitrogen with water removal for three hours. At the end of this period the solution is cooled and concentrated. The residual material is recrystallized from acetonitrile to give 6.8 g of 1-tert-butyl-3-(4,5-dihydro-3-thienyl)urea S,S-dioxide, m.p. 195-197 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; acetic acid;Reflux; | Example 115-Methyl-7-(3-methyl-lH-indazol-5-yl)-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile-l,l- dioxide850 mg (6.336 mmol) dihydrothiophen-3(2H)-one-l,l-dioxide, 1.78 g (6.336 mmol) (2£)-2-[(3- methyl-lH-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A) and 586 mg (7.603 mmol) ammonium acetate in acetic acid (30 ml) were heated to reflux overnight. After cooling, the mixture was evaporated to dryness, and the residue was taken up in ethyl acetate and washed with water and brine. The organic layer was separated and dried over sodium sulfate. After filtration and evaporation to dryness, the remaining solid was purified by preparative RP-ΗPLC (acetonitrile/water gradient) to yield 89 mg (4% of th.) of the title compound.LC-MS (method 5): R, = 1.36 min; MS (ESIpos): m/z = 341 (M+Η)+ 1H-NMR (400 MHz, DMSOd6): δ = 9.73 (s, IH), 7.50 (s, IH), 7.41 (d, IH), 7.24 (d, IH), 4.73 (s, IH), 3.37-3.26 (m, 2H), 3.01-2.93 (m, IH), 2.84-2.77 (m, IH), 2.47 (s, 3H), 2.07 (s, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; acetic acid;Reflux; | Example 107-(lH-Indazol-5-yl)-5-methyl-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile-l,l -dioxide127 mg (0.947 mmol) dihydrothiophen-3(2H)-one-l,l-dioxide, 266 mg (0.947 mmol) (2£)-2-(lH- indazol-5-ylmethylidene)-3-oxobutanenitrile (Example 8A) and 88 mg (1.136 mmol) ammonium acetate in acetic acid (5 ml) were heated to reflux overnight. After cooling, the mixture was evaporated to dryness, and the residue was purified by preparative RP-HPLC (acetonitrile/water gradient) to yield 16 mg (5% of th.) of the title compound.LC-MS (method 5): R1 = 1.31 min; MS (ESIpos): m/z = 327 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): δ = 9.75 (s, IH), 8.05 (s, IH), 7.59 (s, IH), 7.49 (d, IH), 7.26 (d, IH), 4.73 (s, IH), 3.37-3.26 (m, 2H), 3.01-2.93 (m, IH), 2.84-2.77 (m, IH), 2.07 (s, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | at 90℃; for 12h;Neat (no solvent); | Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | at 90℃; for 10h;Neat (no solvent); | Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4. |
A120236 [17396-35-9]
4-Tetrahydrothiopyranone 1,1-dioxide
Similarity: 0.86
A120236 [17396-35-9]
4-Tetrahydrothiopyranone 1,1-dioxide
Similarity: 0.86