HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride → {rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(1-methoxy-1-methyl-ethyl)-phenyl]-4,5-dimethyl-4,5-dihydro-imidazol-1-yl}-[4-(3-methanesulfonyl-propyl)-piperazin-1-yl]-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride | HCID 49853479 | — |
| Reactant | 4,5-Bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(1-methoxy-1-methyl-ethyl)-phenyl]-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride | HCID 73408832 | — |
| Product | {rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(1-methoxy-1-methyl-ethyl)-phenyl]-4,5-dimethyl-4,5-dihydro-imidazol-1-yl}-[4-(3-methanesulfonyl-propyl)-piperazin-1-yl]-methanone | HCID 68683682 | — |
Reaction Steps
In a manner analogous to the method described in example 5, 4,5-bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(1-methoxy-1-methyl-ethyl)-phenyl]-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 1-(3-methanesulfonyl-propyl)-piperazine dihydrochloride (prepared as described in Fotouhi, N. et al. WO 2005110996) to give the title compound as a racemic mixture. The enantiomers were then separated by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Daicel ChiralPak OD-H 3×25 cm, 35° C. at 100 bar, eluting with 30% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C38H49N4O5SCl2 [(M+H)+] 743.2795, observed 743.2795.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07851626B2 |
| Source dataset | uspto-grants-2010_12 |
| ORD ID | ord-ec0580e14e884c71af7cb344a6343051 |
| Source note | uspto-grants-2010_12 |