HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropanol → ethyl((1S)-5-{3-[4-(4-isopropoxy-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | 2-chloro-N,N-dimethylacetamide | HCID 75886 | — |
| Reactant | ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy)-2,3-dihydro-1H-inden-1-yl)acetate | HCID 16110447 | — |
| Product | ethyl((1S)-5-{3-[4-(4-isopropoxy-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate | HCID 16110530 | 49% |
Reaction Steps
A solution of ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (500 mg, 1.1 mmol) (Example 146) and 2-chloro-N,N-dimethylacetamide (800 mg, 6.6 mmol) in i-PrOH (anhydrous, 15 mL) was stirred at 70° C. for 8 h. The reaction was cooled to rt, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc:hexane (v/v)=1.2) gave 292 mg (49%) of the title compound as a yellow oil. LC-MS: RT=4.27 min; (M+H)+: 526.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07714004B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-875db0c3277740db810c8c56a128e078 |
| Source note | uspto-grants-2010_05 |