HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetamide → N-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-yl]acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetamide | HCID 178 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 6-Bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole | HCID 59588803 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-yl]acetamide | HCID 23728857 | 24% |
Reaction Steps
A mixture of 6-bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (480 mg, 1.42 mmol), acetamide (251 mg, 4.26 mmol), Pd(OAc)2 (15.9 mg, 0.071 mmol), Cs2CO3 (694 mg, 2.13 mmol) and xantphos (62 mg, 0.107 mmol) in 1,4-dioxane (10 mL) was heated at reflux for 12 h. Water (5 mL) was added and the mixture was filtered. The filtrate was extracted with EtOAc (3×5 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to give a residue, which was purified by the preparative HPLC to give 108 mg (24%) of N-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-yl]acetamide as a trifluoroacetate salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08772285B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-3351aa586f3a40cc8b5aa2c4f0d2a2eb |
| Source note | uspto-grants-2014_07 |