HCID 67071337, compound → HCID 17754292, compound

HRID 2263913Notes

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.FC(F)(F)C(O)=O.[CH:46]([NH:49][C:50]([N:52]1[CH2:57][CH2:56][CH:55]([N:58]2[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]2)[CH2:54][CH2:53]1)=[O:51])([CH3:48])[CH3:47]>>[CH:46]([NH:49][C:50]([N:52]1[CH2:57][CH2:56][CH:55]([N:58]2[CH2:63][CH2:62][N:61]([C:21]([N:11]3[C@@:12]([C:14]4[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=4)([CH3:13])[C@@:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)([CH3:38])[N:9]=[C:10]3[C:24]3[CH:29]=[CH:28][C:27]([C:30]([C:33]#[N:34])([CH3:31])[CH3:32])=[CH:26][C:25]=3[O:35][CH2:36][CH3:37])=[O:22])[CH2:60][CH2:59]2)[CH2:54][CH2:53]1)=[O:51])([CH3:48])[CH3:47]

Participants

Reactant 2

HCID 67071337HCID 67071337, compound

HCID 72455749rac-(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 17754292HCID 17754292, compound

Procedure

In a manner analogous to the method described in example 5, rac-(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 4-piperazin-1-yl-piperidine-1-carboxylic acid isopropylamide trifluoroacetate 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). LR-MS: 786.0 [(M+H)+]

Sources & evidence

ORD record: ord-7509264f892d41b3844790f58cfcee90
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851626B2

Reaction notes

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