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CAS No. : | 7552-07-0 | MDL No. : | MFCD01102171 |
Formula : | C2H3N3S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | VJHTZTZXOKVQRN-UHFFFAOYSA-N |
M.W : | 101.13 | Pubchem ID : | 290274 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
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 |
---|---|---|
0.711 g | Intermediate F: 5-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)-N-(l,2,4-thiadiazol- 5-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide A solution of tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroisoquinoline-2(lH)-carboxylate (ASW Medchem, Brunswick, NJ, 2.340 g, 6.51 mmol) in 7 mL THF was treated with HC1 4 N in dioxane (8.14 ml, 32.6 mmol) and was allowed to stir at room temperature overnight. LC/MS showed mostly product, so the reaction mixture was concentrated. The resulting residue was triturated with heptane, and the solid was dried and collected . A separate flask charged with l,2,4-thiadiazol-5-amine (1.317 g, 13.03 mmol), 26 mL DCM, and triethylamine (4.54 ml, 32.6 mmol) was cooled to -78 C and was treated with sulfuryl chloride (1.059 ml, 13.03 mmol). After stirring for one hour, the reaction mixture was filtered through a syringe filter and was treated with the 5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l,2,3,4-tetrahydroisoquinoline derived above. After stirring overnight, LC/MS showed product so the reaction mixture was filtered then concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-N-( 1 ,2,4-thiadiazol-5 -yl)-3 ,4-dihydroisoquinoline-2( 1 H)- +H]+ = 423.3 |