1-(Methanesulfonyl)piperidin-4-amine → rac-(4S,5R)-4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carboxylic acid (1-methanesulfonyl-piperidin-4-yl)-amide

HRID 2264002Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:37])[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]([F:33])([F:32])[F:31])=[CH:26][C:25]=3[O:34][CH2:35][CH3:36])=[N:9]2)=[CH:4][CH:3]=1.[CH3:38][S:39]([N:42]1[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44][CH2:43]1)(=[O:41])=[O:40]>>[CH3:38][S:39]([N:42]1[CH2:43][CH2:44][CH:45]([NH:48][C:21]([N:11]2[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)([CH3:37])[N:9]=[C:10]2[C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][C:25]=2[O:34][CH2:35][CH3:36])=[O:22])[CH2:46][CH2:47]1)(=[O:41])=[O:40]

Participants

Reactant 2

HCID 113558261-(Methanesulfonyl)piperidin-4-amine

HCID 73408688rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 72455727rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carboxylic acid (1-methanesulfonyl-piperidin-4-yl)-amide

Procedure

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 1-methanesulfonyl-piperidin-4-ylamine (prepared as described by Bartkovitz, D. J. et al. WO2004069139) to give the title compound. HR-MS (ES, m/z) calculated for C33H36N4O4SF3Cl2 [(M+H)+] 711.1781, observed 711.1778.

Sources & evidence

ORD record: ord-2a01bfcb2f5e49bda544f8ddd1b36add
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851626B2

Reaction notes

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