2-(1-Ethylpropyl)-6-methoxyisonicotinic acid → N-(2-Ethyl-4-{5-[2-(1-ethyl-propyl)-6-methoxy-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenyl)-methanesulfonamide
Reaction equation
[CH2:1]([CH:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[N:14]=1)[C:9]([OH:11])=O)[CH2:4][CH3:5])[CH3:2].[CH2:17]([C:19]1[CH:20]=[C:21]([CH:26]=[C:27]([CH3:34])[C:28]=1[NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:22]([NH:24]O)=[NH:23])[CH3:18]>>[CH2:17]([C:19]1[CH:20]=[C:21]([C:22]2[N:24]=[C:9]([C:8]3[CH:12]=[C:13]([O:15][CH3:16])[N:14]=[C:6]([CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[CH:7]=3)[O:11][N:23]=2)[CH:26]=[C:27]([CH3:34])[C:28]=1[NH:29][S:30]([CH3:33])(=[O:31])=[O:32])[CH3:18]Participants
3
Procedure
The title compound (24 mg) is prepared in analogy to Example 11 starting from 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid (32 mg, 143 μmol) and 3-ethyl-N-hydroxy-4-methanesulfonylamino-5-methyl-benzamidine (40 mg, 150 mmol); LC-MS**: tR=0.91 min, [M+H]+=459.09; 1H NMR (CDCl3): δ0.85 (t, J=7.3 Hz, 6H), 1.36 (t, J=7.3 Hz, 3H), 1.69-1.89 (m, 4H), 2.56 (s, 3H), 2.57-2.65 (m, 1H), 2.93 (q, J=7.5 Hz, 2H), 3.18 (s, 3H), 4.02 (s, 3H), 5.92 (s, 1H), 7.33 (s, 1H), 7.44 (s, 1H), 7.97 (s, 1H), 7.99 (s, 1H).
Sources & evidence
- ORD record
- ord-ee34247045c842c499bb695179612d74
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658675B2
Reaction notes
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