2-Methoxy-6-(3-methyl-butyl)-isonicotinic acid → (S)-3-(2-Ethyl-4-{5-[2-methoxy-6-(3-methyl-butyl)-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diol
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:11]=1)[C:6]([OH:8])=O.CC1(C)[O:22][C@H:21]([CH2:23][O:24][C:25]2[C:34]([CH3:35])=[CH:33][C:28]([C:29]([NH:31]O)=[NH:30])=[CH:27][C:26]=2[CH2:36][CH3:37])[CH2:20][O:19]1>>[CH2:36]([C:26]1[CH:27]=[C:28]([C:29]2[N:31]=[C:6]([C:5]3[CH:9]=[C:10]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[O:8][N:30]=2)[CH:33]=[C:34]([CH3:35])[C:25]=1[O:24][CH2:23][C@@H:21]([OH:22])[CH2:20][OH:19])[CH3:37]Participants
3
Procedure
The title compound is prepared in analogy to Example 1 starting from 2-methoxy-6-(3-methyl-butyl)-isonicotinic acid and (R)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-N-hydroxy-5-methyl-benzamidine; LC-MS: tR=1.14 min, [M+H]+=456.16; 1H NMR (CDCl3): δ 1.00 (d, J=6.3 Hz, 6H), 1.33 (t, J=7.5 Hz, 3H), 1.64-1.74 (m, 3H), 2.41 (s, 3H), 2.77 (q, J=7.5 Hz, 2H), 2.81-2.86 (m, 2H), 3.82-3.94 (m, 2H), 3.94-3.98 (m, 2H), 4.03 (s, 3H), 4.14-4.21 (m, 1H), 7.32 (d, J=0.8 Hz, 1H), 7.49 (d, J=0.8 Hz, 1H), 7.88 (s, 1H), 7.89 (s, 1H).
Sources & evidence
- ORD record
- ord-9d490097de3645cf981cfc87fb8644bd
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658675B2
Reaction notes
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