6-(1-Ethyl-propyl)-4-methyl-pyridine-2-carboxylic acid → N-[(S)-3-(2-Ethyl-4-{5-[6-(1-ethyl-propyl)-4-methyl-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide
Reaction equation
[CH2:1]([CH:3]([C:6]1[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[C:8]([CH3:15])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH2:16]([C:18]1[CH:33]=[C:32]([C:34](=[NH:37])[NH:35]O)[CH:31]=[C:30]([CH3:38])[C:19]=1[O:20][CH2:21][C@@H:22]([OH:29])[CH2:23][NH:24][C:25](=[O:28])[CH2:26][OH:27])[CH3:17]>>[CH2:16]([C:18]1[CH:33]=[C:32]([C:34]2[N:37]=[C:12]([C:10]3[CH:9]=[C:8]([CH3:15])[CH:7]=[C:6]([CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[N:11]=3)[O:14][N:35]=2)[CH:31]=[C:30]([CH3:38])[C:19]=1[O:20][CH2:21][C@@H:22]([OH:29])[CH2:23][NH:24][C:25](=[O:28])[CH2:26][OH:27])[CH3:17]Participants
3
Procedure
The title compound (35 mg) is prepared by coupling and cyclizing 6-(1-ethyl-propyl)-4-methyl-pyridine-2-carboxylic acid (67 mg, 323 μmol) and N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (137 mg, 420 μmol) as described in Example 1; LC-MS*: tR=1.01 min, [M+H]+=497.23; 1H NMR (CDCl3): δ0.85 (t, J=7.5 Hz, 6H), 1.31 (t, J=7.3 Hz, 3H), 1.79 (quint, J=7.0 Hz, 4H), 2.38 (s, 3H), 2.49 (s, 3H), 2.70-2.80 (m, 3H), 3.48-3.56 (m, 2H), 3.75-3.93 (m, 3H), 4.18-4.24 (m, 3H), 7.11 (t, J=5.5 Hz, 1H), 7.16 (s, 1H), 7.90 (s, 1H), 7.91 (s, 1H), 8.00 (s, 1H).
Sources & evidence
- ORD record
- ord-9a20e5d5579a4d22977f687b9c1ee45b
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575200B2
Reaction notes
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