Benzo-1,3-dioxole-5-acetic acid → 3-((Benzo[d][1,3]dioxol-5-yl)methyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

Temperatur

170 °C

As shown in FIG. 2, 2-(benzo[d][1,3]dioxol-5-yl)acetic acid (1 mmol) and thiocarbonohydrazide (1.5 mmol) were heated at 170° C. for 15 min. The mixture was cooled and taken up in 5% MeOH/CH2Cl2 and saturated NaHCO3. The organics were washed with water, saturated NaCl, dried over Na2SO4, and concentrated in vacuo. The resulting 5-((benzo[d][1,3]dioxol-5-yl)methyl)-4H-4-amino-3-mercapto-1,2,4-triazole (compound 1001) was used as is in the next reaction. Accordingly, a mixture of compound 1001 and thiopene-2-carbonyl chloride (0.176 g, 1.2 mmol) suspended in excess phoshoryl chloride (˜10 mL) was refluxed 5 hours. The excess phoshoryl chloride was removed under reduced pressure and the subsequent residue was mixed with crushed ice. The solids were filtered, washed with water, and dried in vaciio. Purification by reversed-phase HPLC produced pure 3-((benzo[d][1,3]dioxol-5-yl)methyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (compound 2).

1. temperatureThe mixture was cooled
2. washThe organics were washed with water, saturated NaCl
3. dry with materialdried over Na2SO4
4. concentrationconcentrated in vacuo
5. customas is in the next reaction
6. temperaturewas refluxed 5 hours
7. customThe excess phoshoryl chloride was removed under reduced pressure
8. additionthe subsequent residue was mixed with crushed ice
9. filtrationThe solids were filtered
10. washwashed with water
11. customdried in vaciio
12. customPurification by reversed-phase HPLC

ORD-Eintrag

ord-ecce3c714f654f259f67249d6ff0a797

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07728017B2