(S)-1-(3-cyclobutoxy-4-methoxyphenyl)-3-(4-fluorobenzyl)piperazine → (S)-1-(4-(3-cyclobutoxy-4-methoxyphenyl)-2-(4-fluorobenzyl)piperazin-1-yl)-2-(1H-pyrazol-4-yl)ethanone

HRID 1423202Notes

Reaction equation

HRID 1423202 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([O:9]C)=O)[CH:3]=[N:2]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][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[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:7](=[O:9])[CH2:6][C:4]4[CH:5]=[N:1][NH:2][CH:3]=4)[C@@H:26]([CH2:30][C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[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 58189210(S)-1-(3-cyclobutoxy-4-methoxyphenyl)-3-(4-fluorobenzyl)piperazineHCID 58189211methyl 2-(1H-pyrazol-4-yl)acetate

Product 1

HCID 58189207(S)-1-(4-(3-cyclobutoxy-4-methoxyphenyl)-2-(4-fluorobenzyl)piperazin-1-yl)-2-(1H-pyrazol-4-yl)ethanoneYield 58%

Procedure

Prepared by the method outlined for Example 275 using methyl 1H-pyrazol-4-ylacetate and (S)-1-(3-cyclobutoxy-4-methoxyphenyl)-3-(4-fluorobenzyl)piperazine as starting materials. Product was obtained as a colorless solid (58%). LC/MS 3.44 min, [M+1]+ 479.

Workup

  1. customPrepared by the method

Sources & evidence

ORD record
ord-7a00bcb86d0d4275a16565fb94a36457
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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