Triethylamine → 5-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-N-tert-butyl-2-chloro-4-ethoxy-benzenesulfonamide

HRID 2263929Notes

Reaction equation

HRID 2263929 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([Cl:42])=[CH:11][C:12]([O:39][CH2:40][CH3:41])=[C:13]([C:15]2[N:16]([C:36](Cl)=[O:37])[C:17]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)([CH3:28])[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)([CH3:20])[N:19]=2)[CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.Cl.[CH3:52][S:53]([CH2:56][CH2:57][CH2:58][N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)(=[O:55])=[O:54]>C(Cl)Cl>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@@:18]2([CH3:20])[C@:17]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)([CH3:28])[N:16]([C:36]([N:62]3[CH2:61][CH2:60][N:59]([CH2:58][CH2:57][CH2:56][S:53]([CH3:52])(=[O:54])=[O:55])[CH2:64][CH2:63]3)=[O:37])[C:15]([C:13]3[C:12]([O:39][CH2:40][CH3:41])=[CH:11][C:10]([Cl:42])=[C:9]([S:6]([NH:5][C:1]([CH3:3])([CH3:2])[CH3:4])(=[O:8])=[O:7])[CH:14]=3)=[N:19]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 498534791-(3-(Methylsulfonyl)propyl)piperazine dihydrochlorideHCID 72455726rac-(4S*,5R*)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl chloride

Product 1

HCID 588943015-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-N-tert-butyl-2-chloro-4-ethoxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(5-tert-butylsulfamoyl-4-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (260 mg, 0.39 mmol, example 45) and triethylamine (350 mg, 3.34 mmol) in methylene chloride (10 mL) was treated with 1-(3-methanesulfonyl-propyl)-piperazine dihydrochloride (110 mg, 0.39 mmol, 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 C38H49N5O6S2Cl3 [(M+H)+] 840.2185, observed 840.2179

Sources & evidence

ORD record
ord-0161b754bb524fb9a1d76c084117c0a5
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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