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

HRID 2425726Notes

Reaction equation

HRID 2425726 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](N3CCN(CCS(C)(=O)=O)CC3)=[O:21])[C:10]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([CH3:49])([CH3:48])[C:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])=[O:42])=[CH:36][C:35]=3[O:50][CH2:51][CH3:52])=[N:9]2)=[CH:4][CH:3]=1.[N:53]1([C:59](=[O:67])[CH2:60][N:61]2[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]2)[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1>>[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:64]3[CH2:63][CH2:62][N:61]([CH2:60][C:59]([N:53]4[CH2:54][CH2:55][O:56][CH2:57][CH2:58]4)=[O:67])[CH2:66][CH2:65]3)=[O:21])[C:10]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([CH3:49])([CH3:48])[C:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])=[O:42])=[CH:36][C:35]=3[O:50][CH2:51][CH3:52])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1006221-(Morpholinocarbonylmethyl)piperazineHCID 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-isobutyramide

Product 1

HCID 57732411cis-2-(4-{4,5-bis-(4-chloro-phenyl)-1-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-N,N-diethyl-isobutyramideYield 85%

Procedure

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, example 157) was reacted with 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (14 mg, 0.0659 mmol, Oakwood Products) using the procedure described in example 25 to give cis-2-(4-{4,5-bis-(4-chloro-phenyl)-1-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-N,N-diethyl-isobutyramide (29.4 mg, 85% yield) as white solids. HR-MS (ES, m/z): observed 791.3445, calculated for C42H52Cl2N6O5 [(M+H)+] 791.3449.

Sources & evidence

ORD record
ord-6f50d1ee6c2b4bf7b63dd31a211a90d4
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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