4-(Piperazin-1-yl)-1lambda6-thiane-1,1-dione dihydrochloride → 3-(4-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-3-methyl-butan-2-one

HRID 2264015Notes

Reaction equation

HRID 2264015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:39])[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]([CH3:35])([CH3:34])[C:31](=[O:33])[CH3:32])=[CH:26][C:25]=3[O:36][CH2:37][CH3:38])=[N:9]2)=[CH:4][CH:3]=1.Cl.Cl.[O:42]=[S:43]1(=[O:55])[CH2:48][CH2:47][CH:46]([N:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)[CH2:45][CH2:44]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:39])[C@:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[N:11]([C:21]([N:52]3[CH2:53][CH2:54][N:49]([CH:46]4[CH2:45][CH2:44][S:43](=[O:42])(=[O:55])[CH2:48][CH2:47]4)[CH2:50][CH2:51]3)=[O:22])[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:35])([CH3:34])[C:31](=[O:33])[CH3:32])=[CH:26][C:25]=3[O:36][CH2:37][CH3:38])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 567734904-(Piperazin-1-yl)-1lambda6-thiane-1,1-dione dihydrochlorideHCID 72455723rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-[4-(1,1-dimethyl-2-oxo-propyl)-2-ethoxy-phenyl]-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 588942873-(4-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-3-methyl-butan-2-one

Procedure

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-[4-(1,1-dimethyl-2-oxo-propyl)-2-ethoxy-phenyl]-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 1-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazine dihydrochloride (example 22) to give the title product 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 35% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C40H49N4O5SCl2 [(M+H)+] 767.2795, observed 767.2790.

Sources & evidence

ORD record
ord-4df6e37de5994d83a4ce35fd04ca4b85
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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