5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → N-((2S)-3-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2-chloro-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide
Reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][C:8]=1[CH3:15])[CH2:4][CH3:5])[CH3:2].[OH:16][CH2:17][C:18]([NH:20][CH2:21][C@H:22]([OH:37])[CH2:23][O:24][C:25]1[C:30]([CH3:31])=[CH:29][C:28]([C:32](=[NH:35])[NH:33]O)=[CH:27][C:26]=1[Cl:36])=[O:19]>>[CH2:4]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:14][N:33]=[C:32]([C:28]3[CH:29]=[C:30]([CH3:31])[C:25]([O:24][CH2:23][C@@H:22]([OH:37])[CH2:21][NH:20][C:18](=[O:19])[CH2:17][OH:16])=[C:26]([Cl:36])[CH:27]=3)[N:35]=2)=[CH:9][C:8]=1[CH3:15])[CH2:1][CH3:2])[CH3:5]Participants
3
Reactant 2
Product 1
Procedure
The title compound (31 mg) is prepared starting from 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (30 mg, 130 μmol) and (S)-2-hydroxy-N-(2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2-chloro-6-methyl-phenoxy]-propyl)-acetamide (39 mg, 117 μmol) according to Method A; LC-MS: tR=0.53 min; [M+1]+=523.14; 1H NMR (D6-DMSO): δ1.03 (t, J=7.0 Hz, 6H), 2.22 (s, 3H), 2.40 (s, 3H), 2.58 (q, J=7.0 Hz, 4H), 3.20-3.29 (m, 1H), 3.40-3.48 (m, 1H), 3.74 (s, 2H), 3.83 (d, J=5.8 Hz, 2H), 3.86-4.01 (m, 3H), 5.32 (d, J=5.3 Hz, 1H), 5.55 (t, J=6.0 Hz, 1H), 7.70 (t br, J=6.0 Hz, 1H), 7.82 (s, 1H), 7.86-7.89 (m, 1H), 7.89-7.90 (m, 1H).
Sources & evidence
- ORD record
- ord-64590d11815245ce93e7958f27c376a5
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148410B2
Reaction notes
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