2-(3-Methyl-1,2,4-oxadiazol-5-yl)propanoic acid → (S)-1-(4-(3-cyclobutoxy-4-methoxyphenyl)-2-isobutylpiperazin-1-yl)-2-(3-methyl-1,2,4-oxadiazol-5-yl)ethanone

HRID 1423199Notes

Reaction equation

HRID 1423199 reaction equation
C[CH:2]([C:6]1[O:10][N:9]=[C:8]([CH3:11])[N:7]=1)[C:3]([OH:5])=O.[CH:12]1([O:16][C:17]2[CH:18]=[C:19]([N:25]3[CH2:30][CH2:29][NH:28][C@@H:27]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:26]3)[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:15][CH2:14][CH2:13]1>>[CH:12]1([O:16][C:17]2[CH:18]=[C:19]([N:25]3[CH2:30][CH2:29][N:28]([C:3](=[O:5])[CH2:2][C:6]4[O:10][N:9]=[C:8]([CH3:11])[N:7]=4)[C@@H:27]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:26]3)[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:13][CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 213129982-(3-Methyl-1,2,4-oxadiazol-5-yl)propanoic acidHCID 58188990(S)-1-(3-cyclobutlyoxy-4-methoxy-phenyl)-3-isobutyl-piperazine

Product 1

HCID 58189030(S)-1-(4-(3-cyclobutoxy-4-methoxyphenyl)-2-isobutylpiperazin-1-yl)-2-(3-methyl-1,2,4-oxadiazol-5-yl)ethanoneYield 4%

Procedure

Prepared by the method outlined for Example 275 using methyl-(3-methyl-1,2,4-oxadiazol-5-yl)acetic acid and (S)-1-(3-cyclobutlyoxy-4-methoxy-phenyl)-3-isobutyl-piperazine as starting materials. Product was obtained as an off-white solid (4%). LC/MS (Method B) 3.8 min, [M+1]+ 443.

Workup

  1. customPrepared by the method

Sources & evidence

ORD record
ord-26769fe1f384438c9d84a2c04aa67e79
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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