HCID 58418037, compound → N-((2S)-3-{2-Chloro-4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide
Reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[N:14]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:17][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]>>[Cl:17][C:18]1[CH:33]=[C:32]([C:34]2[N:37]=[C:9]([C:8]3[CH:12]=[C:13]([O:15][CH3:16])[N:14]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:7]=3)[O:11][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]Participants
3
Procedure
The title compound (135 mg) is prepared in analogy to Example 6 starting from 2-cyclopentyl-6-methoxy-isonicotinic acid (100 mg, 452 μmol) and (S)—N-(3-[2-chloro-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (150 mg, 452 μmol): LC-MS**: tR=0.85 min, [M+H]+=517.21; 1H NMR (CDCl3): δ1.69-1.80 (m, 2H), 1.83-1.95 (m, 4H), 2.06-2.15 (m, 2H), 2.42 (s, 3H), 3.19-3.29 (m, 1H), 3.53-3.61 (m, 1H), 3.81 (ddd, J=14.1, 6.5, 3.5 Hz, 1H), 3.97-4.01 (m, 1H), 4.01 (s, 3H), 4.06 (dd, J=9.5, 4.8 Hz, 1H), 4.21 (s, 2H), 4.21-4.26 (m, 1H), 7.12 (t br, J=6.0 Hz, 1H), 7.27 (d, J=1.3 Hz, 1H), 7.48 (d, J=1.0 Hz, 1H), 7.92 (d, J=1.5 Hz, 1H), 8.05 (d, J=1.8 Hz, 1H).
Sources & evidence
- ORD record
- ord-3d3f5890bbe8411ca9c9693a9e0e12d7
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658675B2
Reaction notes
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