Acetamide → Rac-n-(3-{4-[5-(2-diethylamino-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:22]([C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([NH:31][CH2:32][CH3:33])[N:25]=3)[O:21][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](N(CC)C1N=C(C(O)=O)C=C(C)N=1)[CH3:36].C(N)(=O)C>>[CH2:32]([N:31]([CH2:35][CH3:36])[C:26]1[N:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([C:17]3[CH:16]=[C:15]([CH3:34])[C:4]([O:5][CH2:6][CH:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])=[C:3]([CH3:1])[CH:18]=3)[N:23]=2)[CH:29]=[C:28]([CH3:30])[N:27]=1)[CH3:33]Participants
Reactant 3
Product 1
Procedure
rac-N-(3-{4-[5-(2-Diethylamino-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-diethylamino-6-methyl-pyrimidine-4-carboxylic acid and 2-hydroxy-N-{2-hydroxy-3-(N-hydroxycarbamimidoyl)-2,6-dimethyl-phenoxy]-propyl}-acetamide; LC-MS: tR=1.01 min; [M+H]+=485.30. 1H NMR (D6-DMSO): δ 1.18 (t, J=6.8 Hz, 6H), 2.34 (s, 6H), 2.43 (s, 3H), 3.25 (m, 1H), 3.45 (m, 1H), 3.67 (q, J=6.8 Hz, 4H), 3.70-3.82 (m, 2H), 3.84 (d, J=5.5 Hz, 2H), 3.96 (m, 1H), 5.29 (d, J=5.3 Hz, 1H), 5.55 (t, J=5.5 Hz, 1H), 7.27 (s, 1H), 7.69 (t, J=5.5 Hz, 1H), 7.76 (s, 2H).
Sources & evidence
- ORD record
- ord-89440de2931444c58f8990ea1b69d0f5
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299086B2
Reaction notes
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