[(4S,5R)-2-(4-tert-Butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-[4-(3-ethanesulfonyl-propyl)-piperazin-1-yl]-methanone → 2-(4-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(3-ethanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-2-methyl-propionitrile

HRID 2264048Notes

Reaction equation

HRID 2264048 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:38])[C@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[N:11]([C:21](Cl)=[O:22])[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([C:33]#[N:34])([CH3:32])[CH3:31])=[CH:26][C:25]=3[O:35][CH2:36][CH3:37])=[N:9]2)=[CH:4][CH:3]=1.C(C1C=CC(C2N(C([N:72]3[CH2:77][CH2:76][N:75]([CH2:78][CH2:79][CH2:80][S:81]([CH2:84][CH3:85])(=[O:83])=[O:82])[CH2:74][CH2:73]3)=O)[C@@](C3C=CC(Cl)=CC=3)(C)[C@@](C3C=CC(Cl)=CC=3)(C)N=2)=C(OCC)C=1)(C)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:38])[C@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[N:11]([C:21]([N:72]3[CH2:73][CH2:74][N:75]([CH2:78][CH2:79][CH2:80][S:81]([CH2:84][CH3:85])(=[O:82])=[O:83])[CH2:76][CH2:77]3)=[O:22])[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:31])([CH3:32])[C:33]#[N:34])=[CH:26][C:25]=3[O:35][CH2:36][CH3:37])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 58894220[(4S,5R)-2-(4-tert-Butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-[4-(3-ethanesulfonyl-propyl)-piperazin-1-yl]-methanoneHCID 58894275(4S,5R)-4,5-bis-(4-chloro-phenyl)-2-[4-(cyano-dimethyl-methyl)-2-ethoxy-phenyl]-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 588942112-(4-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(3-ethanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-2-methyl-propionitrile

Procedure

In a manner analogous to the method described in example 5, (4S,5R)-4,5-bis-(4-chloro-phenyl)-2-[4-(cyano-dimethyl-methyl)-2-ethoxy-phenyl]-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 1-(3-ethanesulfonyl-propyl)-piperazine dihydrochloride (example 167) to give the title compound. HR-MS (ES, m/z) calculated for C38H48N5O4SCl2 [(M+H)+] 752.2799, observed 752.2799.

Sources & evidence

ORD record
ord-e33964a76616435db62c42d0b39f045f
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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