5-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazole → 5-[(1R)-2-{4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

HRID 1474417Notes

Reaction equation

HRID 1474417 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[CH:17]=[CH:16][C:12]3=[N:13][O:14][N:15]=[C:11]3[CH:10]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:18][C:19]1[C:27]2[CH2:26][O:25][C:24](=[O:28])[C:23]=2[CH:22]=[CH:21][C:20]=1[C@@H:29]1[CH2:31][O:30]1>>[N:13]1[O:14][N:15]=[C:11]2[CH:10]=[C:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][N:4]([CH2:31][C@@H:29]([C:20]4[CH:21]=[CH:22][C:23]5[C:24](=[O:28])[O:25][CH2:26][C:27]=5[C:19]=4[CH3:18])[OH:30])[CH2:3][CH2:2]3)[CH:17]=[CH:16][C:12]=12

Participants

3

Reactant 2

HCID 151663825-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazoleHCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one

Product 1

HCID 595686635-[(1R)-2-{4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

Procedure

5-[(1R)-2-{4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1 (3H)-one was prepared in a similar fashion as to the synthesis described in EXAMPLE 12 starting from 5-[2-(piperazin-1-yl)ethyl]-2,1,3-benzoxadiazole and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one. LC/MS: [(M+1)]+=423.

Sources & evidence

ORD record
ord-b8c3e3db4b62404bb19c7440ae16697d
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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