(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine → (S)-1-[2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-2-(5-nitro-1H-[1,2,4]triazol-3-yl)-ethanone

HRID 1423232Notes

Reaction equation

HRID 1423232 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:28]([C:31]1[NH:35][N:34]=[C:33]([CH2:36][C:37](O)=[O:38])[N:32]=1)([O-:30])=[O:29]>>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:37](=[O:38])[CH2:36][C:33]1[N:32]=[C:31]([N+:28]([O-:30])=[O:29])[NH:35][N:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazineHCID 1354301112-(5-Nitro-1H-1,2,4-triazol-3-yl)acetic acid

Product 1

HCID 135988893(S)-1-[2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-2-(5-nitro-1H-[1,2,4]triazol-3-yl)-ethanone

Procedure

Prepared using the same procedure described in Example 189 from (S)-3-benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine and (5-nitro-1H-[1,2,4]triazol-3-yl)-acetic acid to afford (S)-1-[2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-2-(5-nitro-1H-[1,2,4]triazol-3-yl)-ethanone as white solid (58 mg). The resulting nitrotriazole was reduced with 10% Pd/C under 1 atm of hydrogen in MeOH to afford the title compound as an off-white solid (15 mg, 39% overall). LC/MS (Method B) 2.20 min, [M+1]+ 491.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4541e10920fd4411bc0792d3e6e7223b
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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