1H-imidazole-2-carbaldehyde → (S)-5-(4-((1H-imidazol-2-yl)methyl)-3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinoline

HRID 1423249Notes

Reaction equation

HRID 1423249 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:28])[F:27])=[N:19]3)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH:35]=O>>[NH:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH2:35][N:13]1[CH2:12][CH2:11][N:10]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:27])[F:28])=[N:19]3)[CH2:9][C@@H:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 249551H-imidazole-2-carbaldehydeHCID 58188941(S)-5-(3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinoline

Product 1

HCID 52920014(S)-5-(4-((1H-imidazol-2-yl)methyl)-3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinolineYield 27%

Procedure

Prepared using the same procedure described in Example 75 from 5-((S)-3-benzyl-piperazin-1-yl)-8-methoxy-2-trifluoromethyl-quinoline and 1H-imidazole-2-carbaldehyde to afford the title compound as a yellow solid (39 mg, 27%). LC/MS (Method B) 2.85 min, [M+1]+ 482.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-adf7721f9537497db66de4170aabd265
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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