Methyl 2-(3-methyl-1,2,4-oxadiazol-5-yl)acetate → (S)-1-(2-benzyl-4-(3-cyclobutoxy-4-methoxyphenyl)piperazin-1-yl)-2-(3-methyl-1,2,4-oxadiazol-5-yl)ethanone

HRID 1423215Notes

Reaction equation

HRID 1423215 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[CH2:26][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.C[O:28][C:29](=O)[CH2:30][C:31]1[O:35][N:34]=[C:33]([CH3:36])[N:32]=1>>[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[CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:29](=[O:28])[CH2:30][C:31]1[O:35][N:34]=[C:33]([CH3:36])[N:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 54453761Methyl 2-(3-methyl-1,2,4-oxadiazol-5-yl)acetateHCID 58188985HCID 58188985, compound

Product 1

HCID 58188997(S)-1-(2-benzyl-4-(3-cyclobutoxy-4-methoxyphenyl)piperazin-1-yl)-2-(3-methyl-1,2,4-oxadiazol-5-yl)ethanoneYield 35%

Procedure

Prepared using the same procedure described in Example 275 from (S)-3-benzyl-1-(3-cyclobutyloxy-4-methoxy-phenyl)-piperazine and (3-methyl-[1,2,4]oxadiazol-5-yl)-acetic acid methyl ester with heating for 5 days to afford the title compound as an off-white solid (49 mg, 35%). LC/MS (Method B) 3.80 min, [M+1]+ 477.

Workup

  1. customPrepared
  2. temperaturewith heating for 5 days

Sources & evidence

ORD record
ord-11837709ee7e44a583297f9a7954ddab
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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