Alternatived Products of [ 116170-90-2 ] Product Details of [ 116170-90-2 ]
| CAS No. : | 116170-90-2 | MDL No. : | MFCD00085050 |
| Formula : |
C9H10N2O2S2 | Boiling Point : | - |
| Linear Structure Formula : | - | InChI Key : | BMYKQPLSSCCDQS-UHFFFAOYSA-N |
| M.W : |
242.32
| Pubchem ID : | 474798 |
| Synonyms : | |
Safety of [ 116170-90-2 ]
| Signal Word: | Warning | Class: | |
| Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
| Hazard Statements: | H302 | Packing Group: | |
| GHS Pictogram: |  |
Application In Synthesis of [ 116170-90-2 ]
* 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.
- Downstream synthetic route of [ 116170-90-2 ]
- 1
[ 5147-80-8 ]
[ 623-51-8 ]
[ 116170-90-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|
| 99% | With triethylamine; In methanol; for 2h;Reflux; | 00461] Step 1: Ethyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2-carboxylate MPI09-013Pl RNWOM PCT FILING[00462] A mixture of [bis(methylsulfanyl)methylene]malononitrile (40 g, 230 mmol), ethylthioglycolate (29 g , 230 mmol) and TEA (24 mL, 173 mmol) in MeOH (600 niL) was allowed to stir at reflux for 2 h. The reaction mixture was allowed to cool overnight and the precipitate was filtered off, washed with cold MeOH (3x50 mL) to give ethyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2- carboxylate (52.4 g, 99 %). LCMS: (FA) ES+ 275. |
| 99% | With triethylamine; In methanol; for 2h;Reflux; | Example 2: 4-(2,4-dichlorophenyl)-2-(2-(fluoromethyl)morphoIino)-5-(4H-l£,4-triazoI- 3-yl)thiophene-3-carbonitrile (Compound 1-11); <n="46"/> [00122] Step 1: Ethyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2-carboxylate; [00123] A mixture of [bis(methylsulfanyl)methylene]malononitrile (40 g, 230 mmol), ethylthioglycolate (29 g , 230 mmol) and TEA (24 mL, 173 mmol) in MeOH (600 mL) was allowed to stir at reflux for 2 h. The reaction mixture was allowed to cool overnight and the precipitate was filtered off, washed with cold MeOH (3x50 mL) to give ethyl 3-amino-4-cyano-5-(methyIsulfanyl)thiophene-2- carboxylate (52.4 g, 99 %). LCMS: (FA) ES+ 275. |
| 72.6% | With triethylamine; In ethanol; at 0 - 20℃; for 12h; | At room temperature, 15.0 g (88.2 mmol) of intermediate 1a and 9.8 mL (88.2 mmol) of ethyl mercaptoacetate were added to 75 mL of ethanol, cooled to 0 C, and 12.2 mL (88.2 mmol) of triethylamine was gradually added dropwise. Reaction at 20 C for 12h. After the reaction was completed, suction filtration was performed, the filter cake was washed with a little ethanol, and dried to obtain 15.5 g of an off-white solid with a yield of 72.6%. |
| 72.6% | With triethylamine; In ethanol; at 0 - 20℃; for 12h; | At 0 C, 2-(Bis(Methylthio)methylene)malononitrile 1 (15.0 g,88.2 mmol) was added to a solution of ethyl 2-mercaptoacetate(9.8 mL, 88.2 mmol) in EtOH (75 mL), then Et3N (12.2 mL,88.2 mmol) was added dropwise to the solution and stirred for12 h at 20 C. The reaction mixture was filtered, washed with EtOH(20 mL) and dried under reduced pressure to afford product 2 as awhite solid (15.5 g, 72.6%). 1H NMR (400 MHz, CDCl3) δ 5.79 (s, 2H).4.28 (q, J 7.2 Hz, 2H) 2.64 (s, 3H) 1.34 (t, J 7.1 Hz, 3H). HRMS (ESI)calculated for C9H11N2O2S2 [M H] m/z 243.0264, found243.0266. |
Reference： [1]Patent: WO2010/90716,2010,A1 .Location in patent: Page/Page column 217-218 [2]Patent: WO2009/154741,2009,A1 .Location in patent: Page/Page column 44-45 [3]Patent: CN110759900,2020,A .Location in patent: Paragraph 0107; 0108 [4]European Journal of Medicinal Chemistry,2020,vol. 197 [5]Organic process research and development,2011,vol. 15,p. 556 - 564 [6]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 3101 - 3106 [7]Chinese Chemical Letters,2012,vol. 23,p. 411 - 414 - 2
- [ 5147-80-8 ]
- [ 116170-90-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|
| 95% | With triethylamine; | Ethyl 3-amino-4-cyano-5-methylsulfanylthiophene-2-carboxylate Ethyl 3-amino-4-cyano-5-methylsulfanylthiophene-2-carboxylate may be prepared by adaptation of the method described in Synthesis 2003, 735, starting with 89.5 g of 2-[bis(methylsulfanyl)methylene]malononitrile and replacing the potassium carbonate with triethylamine. 120.5 g (95%) of crude ethyl 3-amino-4-cyano-5-methylsulfanylthiophene-2-carboxylate are obtained after drying, in the form of a pink powder melting at 149 C. |
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