HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propionyl chloride → N-{4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propionyl chloride | HCID 62324 | — |
| Reactant | 2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine | HCID 3513851 | — |
| Reactant | 4-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine | HCID 10091650 | — |
| Reactant | BEMP resin | HCID 16216994 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-{4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-propionamide | HCID 16748081 | — |
Reaction Steps
According to the procedure described in Example 67, the title compound was prepared by using 4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine, (Example 65), (0.19 g, 0.5 mmol), propionyl chloride (87 uL, 1 mmol, Aldrich), and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine, polymer bound (BEMP resin), (0.34 g, 0.75 mmol) in THF (5 mL). Purification by silica gel chromatography (1:4 of EtOAc/hexanes) provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 445 (M+1). Mp: 196.9–197.6° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07148221B2 |
| Source dataset | uspto-grants-2006_12 |
| ORD ID | ord-a58f160489df4061b05ddfa7dbd56f91 |
| Source note | uspto-grants-2006_12 |