Dimethylformamide → N-(3-{5-[1-(2-Phenoxy-acetyl)-piperidin-2-yl]-[1,2,4]oxadiazol-3-yl}-phenyl)-succinamic acid
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][N:14]3[C:19](=[O:28])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)N[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:29]1(=[O:35])[O:34][C:32](=[O:33])[CH2:31][CH2:30]1.CN(C=[O:40])C>>[O:21]([CH2:20][C:19]([N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[C:10]1[O:40][N:12]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:29](=[O:35])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:7]=[CH:6][CH:5]=2)[N:9]=1)=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
4
Procedure
0.1 mmol of 1-{2-[5-(3-Amino-phenyl)-2H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-2-phenoxy-ethanone were dissolved in 1 ml DMF and 1 eq of succinic anhydride added. The reaction was stirred overnight and the intermediate (N-(3-{5-[1-(2-Phenoxy-acetyl)-piperidin-2-yl]-[1,2,4]oxadiazol-3-yl}-phenyl)-succinamic acid) isolated via preparative HPLC. The isolated material was redissolved in DMF and 1 eq of HATU was added. The reaction mixture was heated to 120° C. using microwave heating. The product was isolated via preparative HPLC.
Sources & evidence
- ORD record
- ord-aef340acf3ab44c1a6bbd65d847cb67b
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645776B2
Reaction notes
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