HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water ethylacetate → (Rs)-2-[2-(1-{1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-ylmethyl)-3h-imidazol-4-yl]-benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water ethylacetate | HCID 22728543 | — |
| Reactant | HCID 67157688 | HCID 67157688 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | (Rs)-2-[2-(1-{1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-ylmethyl)-3h-imidazol-4-yl]-benzonitrile | HCID 67157921 | 30.3% |
Reaction Steps
The compound of example 95 (0.11 g) and copper(I) cyanide (0.03 g) were combined in N-methylpyrrolidinone (5 ml) and the mixture boiled for 6 h. After cooling to room temperature the reaction mixture was stood overnight, diluted with ethyl acetate, passed through silica gel eluting with ethyl acetate/water. The organic phase was separated washed with water dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 20→100% ethyl acetate/pentane), the appropriate fractions combined and solvent removed at reduced pressure to give the title compound (0.03 g) as a gum
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07943645B2 |
| Source dataset | uspto-grants-2011_05 |
| ORD ID | ord-33b68a02da7c4194a926f6b90ce381ff |
| Source note | uspto-grants-2011_05 |