1-(2-Methanesulfonylethyl)piperazine dihydrochloride → HCID 86602332, compound
Reaction equation
ClC1C=CC([CH:8]2[CH:12](C3C=CC(Cl)=CC=3)[N:11]([C:20](Cl)=[O:21])[C:10]([C:23]3C=CC(C(C)(C)COC)=CC=3OCC)=[N:9]2)=CC=1.Cl.Cl.[CH3:40][S:41]([CH2:44][CH2:45]N1CCNCC1)(=[O:43])=[O:42]>>[CH3:40][S:41]([CH2:44][CH2:45][N:9]1[CH2:8][CH2:12][N:11]([CH:20]=[O:21])[CH2:10][CH2:23]1)(=[O:43])=[O:42]Participants
Procedure
4,5-Bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(2-methoxy-1,1-dimethyl-ethyl)-phenyl]-4,5-dihydro-imidazole-1-carbonyl chloride (60 mg, 0.107 mmol, example 153) was reacted with 1-(2-methanesulfonyl-ethyl)piperazine dihydrochloride (42.5 mg, 0.161 mmol, example 17) using the procedure described in example 25 to give 4,5-bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(2-methoxy-1,1-dimethyl-ethyl)-phenyl]-4,5-dihydro-imidazol-1-yl}-[4-(2-methanesulfonyl-ethyl)-piperazin-1-yl]-methanone (70.8 mg) as white solids. The enantiomers were separated by chiral chromatography (Diacel ChiralPak OD, eluting with 40/60 hexane/ethanol). The first peak coming off the column is the desired {(4S,5R)-4,5-bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(2-methoxy-1,1-dimethyl-ethyl)-phenyl]-4,5-dihydro-imidazol-1-yl}-[4-(2-methanesulfonyl-ethyl)-piperazin-1-yl]-methanone (32.1 mg, white solids). HR-MS (ES, m/z): observed 715.2485, calculated for C36H45Cl2N4O5S [(M+H)+] 715.2482.
Sources & evidence
- ORD record
- ord-bad341aeff22445cab0646eab44875e8
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964724B2
Reaction notes
Loading…