Imidazole-4-acetic acid → (S)-1-(2-benzyl-4-(3-isopropoxy-4-methoxyphenyl)piperazin-1-yl)-2-(1H-imidazol-5-yl)ethanone

HRID 1423162Notes

Reaction equation

HRID 1423162 reaction equation
[N:1]1[CH:5]=[C:4]([CH2:6][C:7]([OH:9])=O)[NH:3][CH:2]=1.[CH2:10]([C@@H:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]([CH3:34])[CH3:33])[CH:24]=2)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([C@H:17]1[CH2:18][N:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]([CH3:34])[CH3:33])[CH:24]=2)[CH2:20][CH2:21][N:22]1[C:7](=[O:9])[CH2:6][C:4]1[NH:3][CH:2]=[N:1][CH:5]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 96215Imidazole-4-acetic acidHCID 58189029HCID 58189029, compound2×

Product 1

HCID 58189013(S)-1-(2-benzyl-4-(3-isopropoxy-4-methoxyphenyl)piperazin-1-yl)-2-(1H-imidazol-5-yl)ethanone

Procedure

Prepared by the method outlined for Example 189 using (3H-imidazol-4-yl)-acetic acid and 3(S)-benzyl-1-(3-(1-methylethoxy)-4-methoxy-phenyl)-piperazine (Example 9, Compound 97) as starting materials. Product as an oil. LC/MS (Method B) 2.52 min, [M+1]+ 449. Potency class A.

Workup

  1. customPrepared by the method
  2. customLC/MS (Method B) 2.52 min, [M+1]+ 449

Sources & evidence

ORD record
ord-79067c4f0c754bddaa3c81beee8dd90c
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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