HuagongsheHuagongshe Chemistry Print Report · For research reference only
N,N,N',N'-Tetramethylazodicarboxamide → 1-(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-cyclobutanecarboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N,N,N',N'-Tetramethylazodicarboxamide | HCID 4278 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | Ethyl 1-(4-hydroxyphenoxy)-1-cyclobutanecarboxylate | HCID 59723885 | — |
| Reactant | 2-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole | HCID 66619202 | — |
| Product | 1-(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-cyclobutanecarboxylic acid ethyl ester | HCID 66619404 | — |
Reaction Steps
The title compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Example 1, intermediate c), 1-(4-hydroxy-phenoxy)-cyclobutanecarboxylic acid ethyl ester (CAS RN: 879094-83-4), tri-n-butylphosphin and N,N,N′,N′-tetramethylazodicarboxamide. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow foam (45%). MS (Turbo Spray): m/z=609.3 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08088930B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-60f2548602444f0c9569461269301303 |
| Source note | uspto-grants-2012_01 |