1-(2-Methanesulfonylethyl)piperazine dihydrochloride → cis-2-(4-{4,5-bis-(4-chloro-phenyl)-1-[4-(2-methanesulfonyl-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-N,N-diethyl-isobutyramide

HRID 2425725Notes

Reaction equation

HRID 2425725 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20](Cl)=[O:21])[C:10]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([C:32](=[O:38])[N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])([CH3:31])[CH3:30])=[CH:25][C:24]=3[O:39][CH2:40][CH3:41])=[N:9]2)=[CH:4][CH:3]=1.Cl.Cl.[CH3:44][S:45]([CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)(=[O:47])=[O:46]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:20]([N:53]3[CH2:52][CH2:51][N:50]([CH2:49][CH2:48][S:45]([CH3:44])(=[O:46])=[O:47])[CH2:55][CH2:54]3)=[O:21])[C:10]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([CH3:31])([CH3:30])[C:32]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[O:38])=[CH:25][C:24]=3[O:39][CH2:40][CH3:41])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 177498851-(2-Methanesulfonylethyl)piperazine dihydrochlorideHCID 86602333cis-4,5-Bis-(4-chloro-phenyl)-2-[4-(1-diethylcarbamoyl-1-methyl-ethyl)-2-ethoxy-phenyl]-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 60058550cis-2-(4-{4,5-bis-(4-chloro-phenyl)-1-[4-(2-methanesulfonyl-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-N,N-diethyl-isobutyramideYield 87.2%

Procedure

cis-4,5-Bis-(4-chloro-phenyl)-2-[4-(1-diethylcarbamoyl-1-methyl-ethyl)-2-ethoxy-phenyl]-4,5-dihydro-imidazole-1-carbonyl chloride (27 mg, 0.0439 mmol) was reacted with 1-(2-methanesulfonyl-ethyl)piperazine dihydrochloride (17.5 mg, 0.0659 mmol, example 17) using the procedure described in example 25 to give cis-2-(4-{4,5-bis-(4-chloro-phenyl)-1-[4-(2-methanesulfonyl-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-N,N-diethyl-isobutyramide (29.5 mg, 87% yield) as white solids. HR-MS (ES, m/z): observed 770.2909, calculated for C39H50Cl2N5O5S [(M+H)+] 770.2904.

Sources & evidence

ORD record
ord-75e7d8928ff5402d8ff6ed955d267474
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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