Acetic Acid → HCID 178419476, compound

Temperature

60 °C

To a suspension of 2,4-dibromo-1,3-thiazole-5-carboxamide (0.110 g, 0.385 mmol) in dry toluene (8.0 mL, 75 mmol) was added DMF-DMA (0.204 mL, 1.54 mmol). The mixture was stirred at 60° C. under a nitrogen atmosphere for 3 hours. The solvent was removed and to the intermediate was added acetic acid (2.0 mL, 35 mmol), followed by hydrazine (0.0604 mL, 1.92 mmol). The mixture was heated to 120° C. for 30 min. The mixture was cooled to room temperature, the solvent was removed and the residual acetic acid was azeotroped with toluene (2×5 mL) to give an oily material, which was basified with saturated aqueous NaHCO3 to pH˜8 and extracted with EtOAc (3×30 mL). The EtOAc layer was washed with water, brine, dried over Na2SO4, filtered, and evaporated to give a crude product. Chromatography on a silica column using EtOAc/hexane (0/100 to 50/50) gave a solid product (0.073 g, 61%). LCMS: (FA) ES+ 311 and ES− 309. 1H NMR (400 MHz, d4-methanol) δ: 8.53 (s, 1H).

1. customThe solvent was removed and to the intermediate
2. temperatureThe mixture was heated to 120° C. for 30 min
3. temperatureThe mixture was cooled to room temperature
4. customthe solvent was removed
5. customthe residual acetic acid was azeotroped with toluene (2×5 mL)
6. customto give an oily material, which
7. extractionextracted with EtOAc (3×30 mL)
8. washThe EtOAc layer was washed with water, brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. customevaporated
12. customto give a crude product

ORD record

ord-237dbb10385945d09ee755062ea2fb95

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796271B2