Dimethylamine → rac-N-(3-{4-[5-(4-dimethylaminomethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-di-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1958824Notes

Reaction equation

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

Participants

Reactant 2

HCID 674Dimethylamine

HCID 87208910rac-N-(3-{4-[5-(4-formyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

Product 1

HCID 66932388rac-N-(3-{4-[5-(4-dimethylaminomethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-di-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

Procedure

The title compound was prepared starting from rac-N-(3-{4-[5-(4-formyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide and dimethyl amine according to Method B. LC-MS*: tR=0.78 min; [M+1]+=455.38, 1H NMR (CDCl3): δ2.30 (s, 6H), 2.38 (s, 6H), 3.47-3.53 (m, 1H), 3.54 (s, 2H), 3.75-3.93 (m, 3H), 4.16-4.25 (m, 3H), 7.00 (br s, 1H), 7.53 (d, J=7.8 Hz, 2H), 7.86 (s, 2H), 8.19 (d, J=7.3 Hz, 2H).

Sources & evidence

ORD record: ord-5086e262528745ab8d88ae895f2bd846
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410151B2

Reaction notes

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