N-((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide → Rac-n-(3-{4-[5-(2-isobutylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide
Reaction equation
[CH2:1]([C:3]1[CH:18]=[C:17]([C:19]2[N:23]=C(C3C=C(C)N=C(NCC)N=3)O[N:20]=2)[CH:16]=[C:15]([CH3:34])[C:4]=1[O:5][CH2:6][C@@H:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])C.[CH2:35]([NH:39][C:40]1[N:45]=[C:44]([C:46]([OH:48])=O)[CH:43]=[C:42]([CH3:49])[N:41]=1)[CH:36]([CH3:38])[CH3:37].OCC(NCC(O)COC1C(C)=CC(C(=N)NO)=CC=1C)=O>>[CH2:35]([NH:39][C:40]1[N:45]=[C:44]([C:46]2[O:48][N:23]=[C:19]([C:17]3[CH:18]=[C:3]([CH3:1])[C:4]([O:5][CH2:6][CH:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])=[C:15]([CH3:34])[CH:16]=3)[N:20]=2)[CH:43]=[C:42]([CH3:49])[N:41]=1)[CH:36]([CH3:37])[CH3:38]Participants
4
Reactant 3
Product 1
Procedure
rac-N-(3-{4-[5-(2-Isobutylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide is prepared in analogy to N—((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide using 2-isobutylamino-6-methyl-pyrimidine-4-carboxylic acid and 2-hydroxy-N-{2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2,6-dimethyl-phenoxy]-propyl}-acetamide; LC-MS: tR=0.96 min; [M+H]+=485.31.
Sources & evidence
- ORD record
- ord-ace3042c822b4e81ae38a711d1169b49
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299086B2
Reaction notes
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