1-Methylimidazoleacetic acid → (S)-1-(4-(3-cyclobutoxy-4-methoxyphenyl)-2-isobutylpiperazin-1-yl)-2-(1-methyl-1H-imidazol-4-yl)ethanone

HRID 1423189Notes

Reaction equation

HRID 1423189 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=O)[N:4]=[CH:3]1.[CH:11]1([O:15][C:16]2[CH:17]=[C:18]([N:24]3[CH2:29][CH2:28][NH:27][C@@H:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:25]3)[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH2:14][CH2:13][CH2:12]1>>[CH:11]1([O:15][C:16]2[CH:17]=[C:18]([N:24]3[CH2:29][CH2:28][N:27]([C:8](=[O:10])[CH2:7][C:5]4[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=4)[C@@H:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:25]3)[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH2:12][CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 758101-Methylimidazoleacetic acidHCID 58188990(S)-1-(3-cyclobutlyoxy-4-methoxy-phenyl)-3-isobutyl-piperazine2×

Product 1

HCID 58189157(S)-1-(4-(3-cyclobutoxy-4-methoxyphenyl)-2-isobutylpiperazin-1-yl)-2-(1-methyl-1H-imidazol-4-yl)ethanone

Procedure

Prepared by the method outlined for Example 189 using 2-(1-methyl-1H-imidazol-4-yl)acetic acid and (S)-1-(3-cyclobutlyoxy-4-methoxy-phenyl)-3-isobutyl-piperazine (Example 34, Compound 122) as starting materials. Product as an oil (13.5%). LC/MS (Method B) 2.6 min, [M+1]+ 441.1. Potency class B.

Workup

  1. customPrepared by the method
  2. customLC/MS (Method B) 2.6 min, [M+1]+ 441.1

Sources & evidence

ORD record
ord-2b06ce7cc90c4e059048845dbe37fb4d
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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